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Holiday Rentals in Cape Ann

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    All 143 Rentals in Cape Ann
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    Periwinkle Cottage - Unit 11 / 23
    (30)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Waterfront 2 Bedroom !1 / 14
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Quaint Seaside Village Studio Steps  From Beach1 / 12
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Porch
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2017
    We so much enjoyed this cozy little apartment! It is a great find and well kept with everything you need to enjoy your stay in Rockport. Walk to Bearskin Neck in the heart of...
    Reviewed 21 September 2015
    My husband and I stayed in the studio and loved it. The location is great. You are near all the shops in town and the beach is a block away. The train station is nearby and...
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    About this property
    BOOKING ACCEPTED NOW FOR SUMMER 2018!!. DEDICATED OFF-STREET PARKING FOR ONE CAR. BEST LOCATION IN ROCKPORT steps away from everything! Ground floor studio boasts comfortable and clean efficiency with AC, cable TV and microwave kitchenette, private entrance, private bathroom all on the ground...
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    01966, Rockport, Cape Ann
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town1 / 42
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • Grill
    • Balcony
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 2017
    When we arrived our host met us at the door and let us in, the first thing we noticed was the wonderful view and a balcony to sit on. We were close to most places by walking.
    Reviewed 1 May 2017
    Every where you look out from inside the apt. is a "new picture of the fantastic harbor and boats going out for the catch of the day". Absolutely gorgeous! There is much...
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    About this property
    Reservations from June 22 to end of September must be for 7 nights minimum with Check-in on Friday afternoon. The view is spectacular! The apartment is inside a commercial marine building so it's right on top of the water, where the ships come in to unload lobsters and other catches. The...
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    01930, Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Romantic SUMMERWIND COTTAGE- Scenic Harbor View1 / 26
    (17)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Secure Parking
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2017
    We had a fantastic holiday in Gloucester. Summer wind was the perfect location - the house was beautiful, with all mod cons and fabulous views over the harbour. It was also...
    Reviewed 25 May 2017
    We recently stayed at Summerwind Cottage in Gloucester MA. We thoroughly enjoyed our stay. The decor was wonderfully New England cottage. The living area was cozy with lots...
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    About this property
    Picture a romantic, seaside cottage with a lovely large deck, set on a hillside overlooking the harbor... catching the summer wind, salt air and sounds of seagulls as they drift up from the harbor. Open living space - large living room with sliding door onto large private deck overlooking the...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Family Friendly Apartment, Short Walk to Beach/Downtown, Parking, WiFi, Grill1 / 21
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Grill
    • DVD Player
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2016
    We really enjoyed our stay. Originally from Massachusetts, we looked for a place that would be interesting and relaxing. The rental is perfect. We were comfortable, had...
    Reviewed 19 February 2016
    With two bedrooms, a convenient, well-stocked kitchen, and a homey living room, the Salty Dog was just what we needed for a family getaway to Rockport, MA. Owners were friendly...
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    About this property
    The Salty Dog Summer Stay is a spacious, bright, furnished apartment with all the comfort and amenities one may need to enjoy time in our seaside town. Perfectly located on Atlantic Avenue in the Old Garden Beach neighborhood, many of Rockport's shops, restaurants, and attractions are a short walk...
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    01966, Rockport, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    4 Bedroom Cottage on the Beach!1 / 17
    (5)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Outdoor Dining Area
    • Parking
    • Waterfront
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2017
    We all had a wonderful stay at this ocean front home. The home was very clean and comfortable. The location is great! We had 7 people staying and they all loved it there! The...
    Reviewed 6 October 2014
    We rented this quaint, pretty cottage to celebrate a birthday weekend. Our only complaint is that we didn't have more time to spend here. Jennifer was great to work with-very...
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    About this property
    Sitting directly on picturesque Long Beach, this is the perfect spot for a romantic get-away or a family retreat. With decks in the front and back of the house, sun-chasers and shade-seekers alike will be pleased at any time of day. The cottage is sunny and open with a large eat-in kitchen and...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    Waterfront Woodsy 3BR Cottage1 / 12
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Waterfront
    • Parking
    • Wi-Fi
    • Ocean Views
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2017
    Our family of 4 (plus two standard poodles) thoroughly enjoyed our stay at this charming spot in the Lanesville section of Gloucester. The sunsets are spectacular, it's very...
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    About this property
    Imagine yourself walking across the lawn to the ocean, sweetly lapping the rocks. You take off your sandals and put your feet into the cool water. Second thought, jump right in! Great space for activities; near beaches, restaurants, galleries. The Space This cottage has been hosting travelers and...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM1 / 18
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Grill
    • Ocean Views
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2016
    The Seaward is the perfect getaway! I travelled from Boston to Rockport to take a little break from the city with my boyfriend. It's about a 50 minute drive or you can take the...
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    About this property
    Formerly Seaward Inn, 'The Seaward' continues to offer a spectacular setting and charming accommodations. Here you can fully relax while listening to the ocean waves. Experience the charm, serenity, and unspoiled beauty that is The Seaward. Suite 205, also known as Gully Point, offers...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cozy Rockport Cottage with Ocean Views1 / 14
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 2016
    This simple seaside cottage is well situated to some lovely views of the coast, including the light houses of Thatcher Island. The cottage itself is well-maintained with a very...
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    About this property
    Walk to the water from this cozy peaceful cottage with ocean views. This bright and cheerful recently updated vintage cottage is just minutes from nearby beaches. Enjoy beautiful sunrises, birds chirping, and leisurely strolls along the rugged coast. Stunning views of the Thacher’s Island Twin...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Pet friendly
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    About this property
    Completely renovated 2+ bedroom, 1.25 bath. Second floor unit. Spacious designer kitchen w/ stainless steel appliances. Large Living room and wonderful master bedroom suite. Close to town center, commuter rail, and Singing Beach. 4 minute drive to Singing beach, 20 minute walk (1.2 mile) 2 minute...
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    01944, Manchester-by-the-Sea, Cape Ann
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Ocean Views
    • Terrace
    • Waterfront
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Seaward offers a spectacular setting and charming accommodations. Loblolly Cove, offers accommodations for up to 4 people. One bedroom has a queen sized bed, while the rather spacious living room has accommodations for two more. At Loblolly Cove, you will enjoy a deck with ocean views and...
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    01966, Rockport, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Charming 2 bedroom Rockport Carriage House1 / 14
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Parking
    • DVD Player
    • Patio
    • Shared Garden
    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 October 2014
    We stayed in this fantastic house for over a week with my husband, my sister and her husband. What a wonderful find and what a beautiful place Rockport is. Cannot recommend it...
    Reviewed 4 August 2014
    We stayed in this lovely two bedroom home for two weeks and enjoyed every minute. The location was convenient to down town and various walking trails as well as the other...
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    About this property
    Rockport, a part of Cape Ann, is one of the most scenic towns in Massachusetts located on Boston’s North Shore, Rockport and nearby Gloucester are filled with attractions: art, music, shopping, beaches, whale watching, boating, fishing, bicycling… you name it! Historic Lexington, Concord & Boston...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Captain Quarters1 / 14
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2017
    We stayed for three nights over the July 4th holiday. Perfect location for walking to most places. There is parking right next to the house which is a real bonus in Rockport...
    Reviewed 2 July 2017
    We stayed in the Captain's Quarters of Changing Tides Bed and Breakfast for four nights. THe room's skylight greeted us each morning with blue skies filtered through the...
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    About this property
    Captain's Quarters,at Changing Tides Bed and Breakfast, features a queen-sized bed, two skylights and a shared bath, sleep well and look forward to a gourmet breakfast. Beaches, downtown shops and galleries are all within a short walk of our home. This room is located in the front of our home....
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    01966, Rockport, Cape Ann
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
    • Air Conditioning
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    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Bedrooms, 3 Baths (Sleeps 8) beautiful views, steps to private coffins beach Beautiful single family beach cottage, nestled among the pine trees, located on the private side of Wingaersheek Beach, which is well known as one of the most beautiful beaches on the North Shore, with 1.5 miles of pure...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine a summer of bliss, swimming from the dock at high tide, or from the sandy beach at low tide, when you stay at Annisquam Singing Pines. Or easily paddle to one of the nearby islands or to Wingaersheek Beach for a day in the sand and surf. Annisquam Singing Pines is situated on over an...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    A Year-Round Vacation Home1 / 15
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 2017
    5 adultsHouse is in a great location.Very uncomfortable beds unfortunately. (In all rooms!) -wished there was a queen bed instead of a double in ocean view room-) there...
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    About this property
    $1750 (off season) - $2,100 (peak season) per week .... Fresh sea breezes keep the inside cool during the summer and a large fireplace in the living room makes this a cozy winter getaway. The home comfortably sleeps five, has a completely furnished kitchen, a dining room, and a masonry fireplace in...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • Hot Tub
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just 10 yards from the white sands and lively surf of Long Beach, this vacation rental condo sleeps 8 in central air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named Long Beach is one mile long and spans both Gloucester and Rockport. This...
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    01930, Gloucester, Cape Ann
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stately Victorian home just above Gloucester’s historic harbor evokes the feel of a gracious bygone era. Elegant and spacious, the home has belonged to the same family since the 1880's and was lovingly renovated to offer modern amenities and comfort. Beachmont has a formal parlor, separate...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This bright and open contemporary vacation rental home was custom-designed and built by the architect owner. The care and skill is reflected in the soaring ceilings, multitudes of windows and skylights, and warm pine floors, all of which bring the outside in -- yet all is kept cool with central air...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sea Mist Cottage1 / 18
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    Reviewed 12 November 2017
    We came to celebrate our 32nd anniversary. We absolutely loved the Seamist cottage. There were did many wonderful details that were put into this place, we couldn't list them...
    Reviewed 14 August 2017
    We were extremely happy with our stay. The cottage was very clean and had an ocean theme through out. Everything we needed was there! Our daughter (14) slept in the loft and...
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    About this property
    Seamist Cottage is located on a private yard in historic downtown Rockport, Massachusetts, a charming seaside community. Short walks to shopping and art galleries on Bearskin Neck, beaches, train station as well as the Shalin Liu Perfomance Center. We, as new owners, welcome inquiries & feedback....
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    01966, Rockport, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Antique colonial offering a large place to spend time with family and friends. With lot's of place to sleep and chat. The location is perfect - just across from Stage Fort Park -- featuring a kids playground, Dog Park, Half-Moon Beach, Farmers Market, Sunday summer concert series, Gloucester Blue...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 14
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this bright and delightfully furnished two bedroom vacation rental apartment. It is the perfect place to stay during your New England summer getaway! Both the living room and the...
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    01930, Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Waterfront
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From its waterfront perch, this 4BR vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor and has spectacular, unobstructed views of Sandy Bay. The location of the home is ideal, away from all the hustle of town, but within a 10-15 minute walk to everything you might want,...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    This spacious 5 BR vacation rental home is steps from Old Garden Beach as well as a short stroll into the seaside village of Rockport. Make this delightful house your home base for your beach escape this summer. The main level of the home consists of the gracious and architecturally stunning sun...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    Pet friendly
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    About this property
    Waterfront on Gloucester’s Rocky Neck. Swim from your private beach or from your tidal dock and enjoy the waters of scenic Gloucester Harbor. Nestled close to the shore, vistas abound from its ample deck and most interior rooms. The view of sailboats, Gloucester’s fabled boulevard and the “Greasy...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    About this property
    Enjoy the ambiance of Victorian Gloucester with all the amenities of the 21st century from this classic period vacation rental home, which is tastefully decorated with the traveler in mind. Enter the house through the front door and enjoy two parlors--one with a large bay window and entertainment...
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    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Back Beach1 / 15
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 31 July 2017
    House was wonderful and location perfect. Three generations spending a week making memories and no one was disappointed. Smoke detector battery issue (not something ever...
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    About this property
    Cozy, bright , and ideally located. Unrestricted view of ocean from back of house and large deck. Walk across to Back Beach, 5 minute walk to Front Beach and Main Street downtown. Large fenced yard across from ocean. Beautiful sunrises and sunsets. Train Station 1/2 mile down Granite Street for a...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quaint cozy pre-Revolutionary house with priceless view of picturesque Rockport village and Atlantic Ocean. Located on quiet dead-end lane next to tranquil pond and small town park. Two-minute walk to beach and town's attractive Main street with shops, art galleries and restaurants.The new...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Ocean Front Cottage on Scenic Long Beach1 / 26
    (6)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Front Cottage Directly on the Boardwalk of Scenic Long Beach - Cape Ann, MA Ocean front-row cottage (152 Long Beach) has a 270-degree ocean front view and is the last house facing east on the boardwalk of beautiful & sandy Long Beach. Location allows full views of the twin lighthouses of...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
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    • Waterfront
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique beachfront vacation home has been completely remodeled but retains hints of its historical importance; it was the original U.S. base for the first Trans-Atlantic Cable in 1884. Originating in Ireland, the cable went from Nova Scotia to Cape Ann and back to France. Here is an excerpt...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Wi-Fi
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    Enjoy the comforts of modern day living while you step back in time in this updated colonial-era vacation rental home. From the moment you turn the brass door knob, which is original to the house, you will feel steeped in history. Filled with light from the large windows throughout, and with 4...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Waterfront
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A riverfront property on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river and of Ipswich Bay. You will never forget the sunsets seen from the deck or from the delightful gazebo. This home has a brand new custom kitchen, spacious open concept...
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    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Patio
    • Waterfront
    • Wi-Fi
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rockport oceanfront! This sunlit vacation rental home couldn’t be closer to the water, situated on a bluff overlooking Sandy Bay and Pigeon Cove Harbor. Popples Cove House offers everything you could hope for in a vacation getaway – scenic views, location, privacy, comfort and air conditioning....
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Beach Front, Ocean Views in downtown Rockport1 / 26
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Ocean Views
    • Patio
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 September 2016
    We just returned from Mary's by the Sea in Rockport feeling refreshed, enthused and entirely satisfied with every aspect of our stay. We are bonafide ocean/beach lovers so to...
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    About this property
    Mary's by the Sea in Rockport is located less than one block from downtown and directly across the street from Rockport's best attraction, Front Beach. Walk to shopping, restaurants and the many art galleries that old Rockport is known for. Enjoy excellent privacy from our spacious Ocean View...
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    01966, Rockport, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    One Bedroom Loft Apartment B at Cedar Hill Farm B & B1 / 6
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Wi-Fi
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2017
    This was our first stay in a B&B, it did not disappoint! It was very clean, cozy and conveniently located to the town of Essex. Appreciated the breakfast choices, especially...
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    About this property
    We can now offer Apartment B to our options at Cedar Hill Farm B & B. This apartment is identical to Apt. A also located in our lower barn. The bedroom is on second floor with open to living area and cathedral ceiling. 8 Foot sliders open to open pastures, woods and meadows. Guests can enjoy...
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    Location Information
    01929, Essex, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
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    • Waterfront
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    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gloucester Waterfront Waterfront Vacation House with Dock Direct riverfront home with dock overlooking Annisquam River, Lobster Cove, Wingaersheek Beach, and out towards Ipswich Bay. Open living spaces with endless views of both the river and marshland. This is true waterfront living! So...
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    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Completely renovated 2 bedroom, 1.25 bath. Spacious designer kitchen w/ stainless steel appliances. Large Living room and wonderful master bedroom suite. Close to town center, commuter rail, and Singing Beach. 4 minute drive to Singing beach, 20 minute walk (1.2 mile) 2 minute drive to Train...
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    01944, Manchester-by-the-Sea, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Quarry Crest House: Includes swimming rights to Little Parker quarry1 / 28
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Grill
    • Patio
    • Wi-Fi
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 January 2017
    We had a really nice vacation staying at Quarry Crest House in Rockport with our daughter, son-in-law and 23-month old grandson for nine days. The house was perfect for us with...
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    About this property
    Enjoy the best of all worlds in this spacious and bright vacation rental home overlooking Rockport's stunningly picturesque Flat Ledge Quarry. Not only can you walk to town or to the beach in a few minutes, but the property includes full deeded swimming rights to Little Parker Quarry – a second...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All that Rockport has to offer is within a short walk from this completely remodeled property located in the picturesque Historic District. This vacation rental home gleams with modern amenities yet retains the charm of the original house, which dates from the 1800’s. One of two condo units in the...
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    Location Information
    01966, Rockport, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched overlooking the Wonson Cove’s prismatic waters, this 4 bedroom, 2.5 bath vacation rental home situated in Gloucester’s cultural district known as Rocky Neck will take your breath away. From Eastern Point to the Dog Bar Breakwater, from lighthouses to glorious sunrises, the views from Wonson...
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    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Close to Half Moon Bay1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    • Grill
    • Terrace
    • Patio
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your morning coffee and breathtaking sun rises on the covered porch, listen to the birds singing before you walk to Half Moon beach for a relaxing day at the ocean. Private entrance, dedicated parking spot on premise, fully equipped kitchen (with fridge, oven, stove, microwave, coffeemaker,...
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    01930, Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    About this property
    Ideally situated between two of Cape Ann's most beautiful beaches, this ideal vacation rental home is a mere 3-minute walk to Long Beach and an 8-minute walk to Good Harbor Beach. The home has a single level and an open floor plan that offers convenience and practicality. For comfort, each of the...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Waterfront
    • Patio
    • DVD Player
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This waterfront vacation rental is a wonderful inviting family vacation home with bountiful space, located in the highly desirable area of 'The Avenues' at the northern end of Rockport. Boasting 5 bedrooms/3.5 baths and the ability to comfortably sleep 12 people, this is a house to bring the...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This inviting family vacation home has bountiful space and is located in the highly desirable area of 'The Avenues' at the northern end of Rockport. Boasting 6 bedrooms, 3.5 baths and the ability to comfortably sleep 10 people, this is a house for the extended family to enjoy. This area of Rockport...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    SEASIDE GARDENS AFFORDABLE GUEST ROOM(S)  IN VILLAGE BY BEACH, WALK EVERYWHERE!1 / 15
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    • Private Garden
    • Balcony
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 October 2017
    Loved our stay at Gloucester Harborview Inn . Great location, spotlessly clean and very welcoming . Highly recommend
    Reviewed 16 March 2017
    I had a wonderful stay at this lovely charming bed and breakfast. Location, accommodations and hostess were excellent.Highly recommend!
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    About this property
    Are you looking for a conveniently located affordable place to stay while you enjoy all that Rockport has to offer? Are you traveling with family or friends and would like the privacy of separate rooms? Our top floor guest rooms (2 available) are perfect for travelers on a budget. Clean and...
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    01966, Rockport, Cape Ann
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    La Boheme RETREAT Studio1 / 26
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Patio
    • Central Heating
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 September 2016
    This unit was a great location! It was easy to get to the train to go into Boston as well as to travel to other sites in and around Boston. My daughter and I loved to sit on the...
    Reviewed 27 January 2015
    I had a chance to stay at this wonderful studio for 2 weeks and couldn't my believe good luck. This property, a former Unitarian Church and sexton's residence, has been...
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    About this property
    UNPLUG, UNWIND & UPLIFT your spirits! No TV (wifi only). For those seeking to truly rest, relax, rejuvenate and contemplate their journey on earth. Step back in time with this 60's Boho, funky-style studio. Creative objets d'art and romantic lighting creates a very cozy, dark atmosphere (a...
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    Location Information
    01930, Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your family will love this extraordinary waterfront vacation rental home with spectacular views. Set on a bluff over picturesque Strawberry Cove and the open Atlantic, views abound from almost every light-filled room. The house offers three levels of sophisticated, yet comfortable living space....
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    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    • Grill
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacy Boulevard is home to the iconic 'Gloucester Fisherman at the Wheel' sculpture -- a symbol of the fishing port's rich history as a working waterfront and as the subject of poets,...
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    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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