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Elder Access Holiday Rentals in Southold

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    RM 1,676 Average
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    Travellers to Southold are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    20 Matching Rentals in the Southold AreaView all 38 rentals
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    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES1 / 17
    (2)Excellent
    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Southold
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Grill
    • Private Garden
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large beach front with 5 bedrooms (2 ensuite), 4 living rooms, 3.5 baths This is the perfect home for the extended family vacation, with not only 5 bedrooms, including 2 with ensuite bathrooms but 4 separate sitting/family/den or game rooms plus a pool room! The unique layout offers areas to gather...
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    11971, Southold, North Fork
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms 3 Bathroom home for rent. Beautiful landscape and privacy on a full acre with gigantic fenced in backyard with playground. 5 minute walk or 1 minute drive to private community Peconic Bay beach. Excellent condition and comfort. Weber Grill, sun filled deck , quality entertainment system....
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    11971, Southold, North Fork
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Ocean Views
    • Washer
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    near beach 3 Bedrooms and 1.5 baths Plus and outdoor shower, nice yard,WiFi,bbq Begin Description: Awesome Beach House (less than 50 yards [30 second walk to the beach] from private sandy bay beach) location location location This House was built in the 1700's (revolutionary era) and has been...
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    11971, Southold, North Fork
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Garden
    • Cable/satellite TV
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Guests are sure to enjoy a memorable vacation in this Pristine 3 bedroom/2 bath contemporary property in a quiet bay front community located steps away from a private beach facing Shelter Island and across from a well known North Fork vineyard. This property is located on a quiet dead end street...
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    11971, Southold, North Fork
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The following rentals are within 10 kilometres of Southold.
    Cutchogue Beach Cottage1 / 36
    (9)Excellent
    Cutchogue
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Outdoor Dining Area
    • Washer
    • Wi-Fi
    • Grill
    • Patio
    • Central Heating
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2016
    We had a very happy stay here. Contact with Julie was first class, the house is very tastefully decorated and comfortable. It is ideally situated to explore further but has...
    Reviewed 9 August 2016
    We so enjoyed our time here. You really can't find a more homey cottage and the close proximity to the great beach and scenic hilltop playground was tops. Julie was wonderful...
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    About this property
    Cozy Cutchogue Beach Cottage on the North Fork of Long Island. It has 2 bedrooms with queen sized beds and there is a sleeping loft appropriate for children over 9 years old (one queen sized bed and one twin). Deck and backyard with gas grill, outdoor picnic table, fire pit, and tire swing....
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    11935, Cutchogue, North Fork
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Cutchogue
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Patio
    • Private Garden
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated cottage has a spacious living room, large eat-in-kitchen, 2 bedrooms; one with queen-sized bed, the other with two twins, and one full and one half bath. There is a waterview across the street from the relaxing 'pebble lounge' the garden seating area in front of the house....
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    Location Information
    11935, Cutchogue, North Fork
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 1828 for a ship’s captain, this historic property remains as one of the oldest structures in the village. Original details abound. Large, bright & airy rooms. Brand new furnishings. Perfect for entertaining or a quiet weekend retreat. The Space Located on a tree lined street this...
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    Location Information
    11944, Greenport, North Fork
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    The Farmhouse1 / 15
    (1)Very good
    Greenport
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 February 2017
    My family rented this house for the holiday week between Christmas and New Years. The house is located within walking distance to town - which was quite great The house has...
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    About this property
    Renovated and tastefully furnished, The Farmhouse features one of the largest wrap around porches in the village and it is enviably located steps away from the town's best restaurants and bars, as well as just 3 short blocks to the beach. The space Just steps away from the center of the Greenport...
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    Location Information
    11944, Greenport, North Fork
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Victorian Seasons Stirling1 / 32
    (3)Excellent
    Greenport
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    Victorian Seasons Stirling is a breathtaking home on a very large beautiful property!This was a weekend trip with 3 couples. The house is a gorgeous Victorian style home totally...
    Reviewed 16 March 2018
    A group of childhood girlfriends looking for a getaway and one of my girlfriends took care of all the arrangements. We arrived Friday afternoon to a warm welcome tour by the...
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    About this property
    Elegant and especially designed and built for one of the wealthiest bankers on the North Fork. Situated on enormous property in the most prestigious setting of the National Historic District in Greenport Village. Lovingly restored to its original elegance and authentic Classic Queen Anne...
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    Location Information
    11944, Greenport, North Fork
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    Greenport
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will love this 4 bedroom 4.5 bathroom charmer on a quiet street. Walk to town, shops, carousel LIRR Jitney and ferry to Shelter Island Golf course and beaches 1 mile away. There are over 40 wineries nearby. The front deck has 2 Adirondack chairs to just relax. A full deck off the back over...
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    11944, Greenport, North Fork
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    Greenport
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1903 Village Farmhouse, full of character, light and air. A place to relax, unwind and drink wine on the front porch, say hello to our neighbors or take an afternoon nap. Walk into the village for shopping and dinner or ride your bike to the beach. Visit one of the many local wineries and stop...
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    Location Information
    11944, Greenport, North Fork
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    North Fork Beach House on LI Sound1 / 14
    (1)Excellent
    Peconic
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Housekeeping Included
    • Air Conditioning
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 April 2018
    House had everything we needed to enjoy a vacation at the beach. Great outdoor barbecue area, huge outdoor shower. Sunsets are amazing from the deck!Comfortable beds and...
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    About this property
    Enter a world of tranquility and surround yourself with the beauty of nature! Decorated with an eclectic mix of antique and contemporary furniture, the home has three bedrooms, one bath, dining room, living room with large flat screen tv, sunroom with seating and dining area. Kitchen is remodeled...
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    11958, Peconic, North Fork
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    New Suffolk
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
    • Porch
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A renovated home in the heart of the North Fork near the beach and several wineries. Please inquire about weekends, weeks or monthly/summer rental for 2015. Sleeps 8 Enjoy a bright renovated home with 12 skylights, cathedral ceilings and entirely new furnishings only ¼ mile to Cutchogue harbor and...
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    11956, New Suffolk, North Fork
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cutchogue
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Grill
    • Cable/satellite TV
    • Washer
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A new Fleets Neck home( May 2017), 2 blocks from Wickham Creek and a 10 minute walk to a lifeguard protected town beach and park. Beach parking permit supplied. Enjoy great restaurants and wineries near by. Sit on the covered front porch and commune with the wildlife while enjoying morning coffee....
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    Location Information
    11935, Cutchogue, North Fork
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cutchogue
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home is relatively brand new, four bedrooms and 3 and a half bathrooms. Master suite with bathroom, and an additional bedroom with private bathroom. Two Bedrooms share a bathroom. Home is located on two acres of privacy. Beautiful pool and landscaping. Owner has a basement apartment that will be...
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    Location Information
    11935, Cutchogue, North Fork
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Designed and built in 2003, this cozy house has water views of Peconic Bay, enormous glass skylights, fully equipped kitchen, two bedroom, two bath, washer, dryer, Wifi, flat screen tv, private rose garden, private parking, a kayak, two bicycles, public swimming dock at end of block, and is one...
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    11944, Greenport, North Fork
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated ranch private home with spacious deck, large teak dining set, new grill, CAC, washer/dryer, front porch, fully equipped kitchen, wall mounted flat screen TVs in every bedroom and family room, farm dining room table. Nicely appointed home within walking distance to gorgeous private...
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    Location Information
    11944, Greenport, North Fork
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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