We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals near Wingaersheek Beach

Gloucester, Massachusetts
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    RM 2,315 Average
    |||
    |||
    RM 0RM 4,000+
    Suitability
    More filters
    Travellers to Gloucester are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    All 65 Rentals in Gloucester
    Romantic SUMMERWIND COTTAGE- Scenic Harbor View1 / 30
    (17)Excellent
    5.6 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Stunning SUNSET STUDIO w/Scenic Harbor View1 / 29
    (5)Excellent
    5.6 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    5.9 kilometres from Wingaersheek Beach
    7 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check-in Check-out
    Show Prices
    La Boheme RETREAT Studio1 / 26
    (3)Very good
    5.6 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Lovely 'Blue Heron Cottage' on Annisquam River!1 / 24
    (1)Excellent
    4.3 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Washer
    • Wi-Fi
    • Waterfront
    • Parking
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2017
    We walked to the beach at Good Harbor and enjoyed crossing the sandbar at low tide to Salt Island. Two grocery stores, liquor store were very close. Gloucester had a small...
    See all reviews
    About this property
    Located less than 5 miles from beautiful beaches, popular parks and local hot spots, the ‘Blue Heron Cottage’ is the perfect New England escape. Head down to Stage Fort Park for a waterside picnic or enjoy riverfront dining right here at home! This 3-bedroom, 1-bath vacation rental sits on the...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    At the Footbridge entrance to Good Harbor Beach1 / 17
    (2)Very good
    5.8 kilometres from Wingaersheek Beach
    6 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Terrace
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 April 2017
    This beachhouse is a dream. Classy beautiful old beachhouse yet super comfy and homey. Plenty of room and different spaces to accommodate a family with a variety of interests...
    Reviewed 26 October 2016
    Great place to spend a week or more with your entire family. Large house with big kitchen and dining room for family dinners. Walk across the bridge to the beach or sit on the...
    See all reviews
    About this property
    At the edge of Good Harbor Beach, one of the very best beaches in all of New England. Good Harbor Beach, less than 1 hour north of Boston, has a fine white sandy bottom, is cleaned daily, beautiful surf. little undertow, incorporates a saltwater creek. Great for children. 1890s 2-storey cottage...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 10
    5.9 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    6.1 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Grill
    • Parking
    • Washer
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location! This vacation home is large and comfortable and is just steps to the white sands and surf of Good Harbor Beach. The location offers the best of all worlds as it is so close to Cape Ann's most popular beach and also has water views of Bass Rocks. This dramatic rocky bit...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    1.7 kilometres from Wingaersheek Beach
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    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...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    1.7 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Waterfront
    • DVD Player
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all and unwind at this comfortable riverfront vacation retreat. Located in a quiet neighborhood, Thurston Point Cottage offers a relaxing atmosphere with spectacular sunset views over the Annisquam River. You might choose to sip a cool drink on one of the large porches and watch...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
    Save time - get the best Gloucester rentals sent straight to your email!
    Get the List
    5.9 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • Wi-Fi
    • Grill
    • DVD Player
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    5.3 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Parking
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will love this extraordinary waterfront vacation rental home with spectacular views and top-notch amenities. Set on a bluff over picturesque Strawberry Cove and the open Atlantic, water views abound from almost every room. The house offers a sophisticated, yet comfortable living space, full of...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    5.0 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • Grill
    • Wi-Fi
    • Terrace
    • DVD Player
    • Balcony
    • Cable/satellite TV
    Suitability
    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,...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    1.3 kilometres from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront 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 custom kitchen, spacious open concept living/dining room and...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    5.6 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in a quiet, leafy neighborhood, Family Tides offers convenience and comfort, just a half-mile to Gloucester's Good Harbor Beach. Cathedral ceilings with skylights, large picture windows, and French doors to the deck illuminate the the open-plan main floor. Starting in the fully-applianced...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    6.1 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Parking
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely beach house has it all: prime Good Harbor Beach location, views, historic charm and modern comfort and style. The original cottage was built as a stone carriage house to a neighboring estate. A wonderful octagonal addition has created a three bedroom/two full bath home that boasts a...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    6.1 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. The location for this...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    2.8 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Patio
    • Grill
    • Balcony
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Gloucester, America’s oldest seaport! This two acre, family-friendly, contemporary private retreat on Gloucester’s Rust Island offers 4 Bedrooms with stunning panoramic views of beautiful marshes and the Jones River, which flows into the Annisquam River and Ipswich Bay. Surrounded by...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    4.1 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Parking
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Picture yourself on the huge wraparound deck of Ships Bell House, enjoying the setting of the sun over breathtaking water views. That's the moment you'll never forget when you stay in this charming vacation rental home in Gloucester's Lanesville neighborhood. Ships Bell House is located on a...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1.2 kilometres from Wingaersheek Beach
    6 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Parking
    • Grill
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cedar Ledge Annisquam (formerly known as Annisquam Heights) is a classic New England vacation home that pays homage to the past but has modern sensibilities. From the vast wraparound porch, you'll be able to relax and catch salty sea breezes while taking in the incredible ocean views. Inside, the...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 14
    List your property for free!
    List your holiday rental where Tripadvisor travellers can find it.
    Add a Listing
    1.1 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of the quaint and charming village of Annisquam, this newly renovated Gloucester cottage offers the perfect vacation spot. The bright and airy ground floor has many windows, letting in lots of natural light. Upstairs, there are 3 bedrooms and a full bath with claw foot tub and...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    5.8 kilometres from Wingaersheek Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Terrace
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New Property for 2020. Plaisance is a comfortable modern home nestled in a quiet, leafy neighborhood not far from Good Harbor Beach and the Bass Rocks Golf Club. The ground floor is open and airy and lets in plenty of natural light throughout the day. The living room is perfect for keeping the...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    5.6 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Hot Tub
    • Parking
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just up the street from Good Harbor Beach, this well-appointed and perfectly located vacation rental is the ideal home base for your Gloucester beach vacation with family or friends. Over By Good Harbor sits prominently on a grassy knoll with abundant views of Good Harbor Beach and the sea beyond....
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    2.3 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • Terrace
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated on a knoll in Gloucester's Bay View neighborhood, Helena House offers peekaboo views of Ipswich Bay from the second floor bedroom with deck. Decorated with a European sensibility, the home is sunny, comfortable and cheerful, with hardwood floors throughout. A Queen Anne-style house, you...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
    2.0 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Waterfront
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll find river life at its best when you stay at this newly-built vacation rental home that sits along the banks of scenic Annisquam River in Gloucester. From the private patio, you will be mesmerized by spectacular sunsets and the parade of boats as they sail, motor, or paddle by. Annisquam...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    5.7 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Grill
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfectly-located vacation rental is a delightful ground floor apartment (in a two-unit building), right at Good Harbor Beach. With one bedroom and sleeping space for 3, this beach house is the perfect arrangement for couples and small families. Just step out the door, walk over the Good...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    4.4 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the beauty of Cape Ann at this romantic cottage. Direct ocean front in America's oldest seaport. Immaculate 2 bedroom cottage brings back memories of long ago. At the end of a dirt road, the cottage offers a wrap around porch, rolling green grass, granite steps leading to a flat rocky...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    3.8 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Grill
    • Ocean Views
    • Patio
    • Washer
    • Balcony
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront tri-level, with 4 bedrooms, 2 full baths, fire pit and a dock will accommodate up to 10 people. Located on Little River overlooking the water, the yard, screened porch and patio face west for the most spectacular sunsets. Launch your trailered boat at the public launch or use your...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    1.2 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Patio
    • Air Conditioning
    • Parking
    • Waterfront
    • Wi-Fi
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Greet each day with inspiring views of the Annisquam River from this charming vacation home and enjoy the most spectacular sunsets each evening. Terra Nova offers that 'get away from it all' feeling, with a large verdant lawn, breathtaking water views, and comfortable furnishings. Inside, find an...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1.1 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Terrace
    • Waterfront
    • Grill
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully renovated home is located directly on Lobster Cove in the historic village of Annisquam. Around 1623, Captain John Smith described the cove as a 'a safe harbor in a Northeast storm.' Nothing has changed. Swim from your own private dock where there is a paddle board and kayak for...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Cottage at the Cove: A delightful vacation home close to Plum Cove Beach.1 / 27
    (1)Excellent
    2.7 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2020
    I highly recommend this location. The house is wonderful, super cute, super clean, and has EVERYTHING you could possibly need (we especially appreciated the beach chairs...
    See all reviews
    About this property
    Cottage at the Cove is a bright, inviting vacation home situated in Gloucester's charming Bay View neighborhood that radiates an aura of sun and warmth. Just a short walk down the lane to Plum Cove Beach to spend your summer vacation relaxing by the water, discovering local fauna, swimming to your...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    6.0 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2021! Centrally located in the heart of East Gloucester, The Mount is a beautiful rental home in close proximity to the America's oldest art colony and to one of Cape Ann's many beaches, Niles Beach. The location is also ideal for theater goers and art lovers to take in a top-rated...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3.7 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Exquisitely renovated by the owner-architect, every detail of this charming vacation home has been thoughtfully considered. Located in an American Foursquare home on a quiet dead end street, it's backyard fronts the Annisquam River. Relax on the deck and watch the boats or launch a kayak in at high...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 4
    2.3 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience river life at its best along the banks of Mill River when you stay at this spectacular waterfront rental home with exquisite water views, a large back yard, and a private tidal dock for swimming and kayaking. For the full river experience, ask us about renting a Kayak or Stand-Up...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1.1 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Terrace
    Suitability
    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...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1.3 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check-in Check-out
    Show Prices
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy casual and carefree living in West Gloucester this summer! Just a half mile from Wingaersheek Beach, this charming single-story cottage awaits your arrival. The living room’s cathedral ceiling lends an airy feel to the space and your eyes will be riveted to the windows that offer a surprising...
    View all property information
    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    The Sail Loft of Bearskin Neck- Old Harbor Retreat1 / 17
    (1)Excellent
    6.0 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2018
    We loved our stay at the Sail Loft—the apartment has all the amenities we needed (including air conditioning!) and was a pleasure to cook and relax in. If you like being in the...
    See all reviews
    About this property
    The Building was once the historic Sail loft- oozing with character and charm. Inside is a 2 Bedroom, 1 Bath apartment unit. A good sized living area with a leather couch, TV with Netflix and Amazon Prime TV & dining table that can fit up to 6. There is a small patio in front with a table, bench...
    View all property information
    Location Information
    Rockport, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Back Beach1 / 15
    (2)Excellent
    5.3 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet1 / 23
    (44)Excellent
    5.5 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Outdoor Dining Area
    • Parking
    • Cable/satellite TV
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2019
    This is truly a home away from home. A short walk to town where parking is at a premium. Stocked with everything you might need, with extra touches like a new kitchen sponge...
    Reviewed 28 July 2019
    Dear Rosemarie and Family!Our second lovely stay in #1 Periwinkle Cottage!So rejuvenating – we had to stay the extra day! We are very grateful for the ease of keeping our...
    See all reviews
    About this property
    OPEN YEAR ROUND - 2 night minimum stay. 2019.. Celebrating our 10th year hosting guests from all over the world! PERIWINKLE COTTAGE - truly a place to call 'a home from home'. This 2-unit, townhouse cottage offers guests privacy and an updated seaside decor with today's modern amenities. (You...
    View all property information
    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    5.9 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Washer
    • DVD Player
    • Grill
    • Waterfront
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Rockporter is a charming waterfront vacation rental home that sits on a quiet lane in Rockport's Pigeon Cove. You'll be as close to the ocean as one can be on Cape Ann, enjoying sweeping views of Sandy Bay from most rooms in the house. Set up to comfortably sleep 7, the house has an eat-in...
    View all property information
    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    18th Century Cottage with attached guest suite1 / 21
    (1)Excellent
    5.4 kilometres from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 October 2016
    We just completed our first visit here and plan to return to this house. A Very clean, historic home that more than met our expectations. It is off the beaten path with both...
    See all reviews
    About this property
    Down a quaint lane you will find an Artists cottage and guest suite. The smaller of the two buildings contains a private double bed retreat with en suite, cable TV & Wi fi. The Main house boasts a charming loft bedroom with 2 ex-long twin beds. The ceiling of the second floor bathroom is a large...
    View all property information
    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    5.5 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From it's private deck, enjoy the views of Sandy Bay dotted with sailboats. Or, walk down the quiet lane to Granite Pier and experience the unsurpassed views of the sun rising over the Atlantic Ocean, and of fishing boats moored nearby. The full moon over Granite Pier is spectacular, and even...
    View all property information
    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    5.4 kilometres from Wingaersheek Beach
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Parking
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and enjoy all that Cape Ann has to offer at Happy Days Cottage, across the street from enchanting Folly Cove. Right at the waterfront, there is a shared deck from which you can take in the views, or you can walk down to the water to swim or launch your kayak. The cottage is bright and...
    View all property information
    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
    Quaint Seaside Village Ground floor Studio Steps  From Beach WITH PARKING1 / 12
    (7)Excellent
    5.6 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Porch
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2020
    Wendy was a fabulous hostess! We had a kitchen stocked with cereals, milk, soda and cold water in the fridge, ice, and even a small cooler on top of the fridge. Wendy was warm...
    Reviewed 24 August 2018
    What a wonderful place!! I had the upstairs to myself as well as a living room. Wendy has thought of everything! Very hospitable. I wish I could have stayed here for a month...
    See all reviews
    About this property
    WEEKLY BOOKINGS ACCEPTED NOW FOR SUMMER 2020!!. 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, WIFI, cable TV and microwave kitchenette, private entrance, private bathroom all on...
    View all property information
    Location Information
    Rockport, Cape Ann
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Quarry Crest House: Includes swimming rights to Little Parker quarry1 / 27
    (1)Excellent
    5.4 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Patio
    • Wi-Fi
    • DVD Player
    • Parking
    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...
    See all reviews
    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 you can also swim at the nearby quarry, Little Parker's Pit. This is a sparkling fresh...
    View all property information
    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    5.9 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Grill
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Midway between two picturesque places, the seaside village of Rockport and the historic fishing port of Gloucester, Sage Hill is the perfect vacation destination. Walk to Long Beach (it’s about a 5 minute walk), or take a short drive to Good Harbor Beach. Sage Hill is well appointed, with a...
    View all property information
    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Beach &  King Street Inn / Beach House Rental1 / 20
    (4)Excellent
    5.5 kilometres from Wingaersheek Beach
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • Porch
    • DVD Player
    • Cable/satellite TV
    • Parking
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    Parking was a little tricky and I have to say I was quite concerned when we first arrived. However, Tim was there to greet us and made sure we found appropriate parking for all...
    Reviewed 8 August 2017
    The Beach & King is the perfect vacation home for our four generation family. The house is spacious and beautifully decorated. The front porch is a lovely spot to enjoy...
    See all reviews
    About this property
    Located across from Rockport's Front Beach, Beach & King Beach House is an intimate Cape Ann home located on the North Shore in Massachusetts. Accommodations at our Rockport home offer a picturesque setting with stunning ocean views and a 5-minute stroll to historic Bearskin Neck and the village....
    View all property information
    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    5.8 kilometres from Wingaersheek Beach
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Parking
    • Grill
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
    View all property information
    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
    SEASIDE GARDENS AFFORDABLE GUEST ROOM(S)  IN VILLAGE BY BEACH, WALK EVERYWHERE!1 / 15
    (3)Excellent
    5.6 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Terrace
    • Private Garden
    • Balcony
    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!
    See all reviews
    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...
    View all property information
    Location Information
    Rockport, Cape Ann
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    5.4 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Grill
    • DVD Player
    • Parking
    Suitability
    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...
    View all property information
    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1
    List your property
    Owner log in
    © 2021 TripAdvisor LLC All rights reserved.

    This is the version of our website addressed to speakers of English in Malaysia. If you are a resident of another country or region, please select the appropriate version of Tripadvisor for your country or region in the drop-down menu.