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Southold House Rentals

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    Travellers to Southold are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    26 Matching Rentals in the Southold AreaView all 42 rentals
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    Beautiful Classic North Fork Home, wrap around porch, pool, walk to beach1 / 19
    (1)Excellent
    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Patio
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning views, master suite, deck, sunrooms, private lane and beaches Completely renovated and handicapped accessible throughout with wrap around deck, extra wide doorways, new kitchen, two and a half new bathrooms with tubs and showers and large master bedroom suite overlooking the Ashamomaque...
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    Southold, North Fork 11971
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Southold
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Grill
    • Private Garden
    • Internet Access
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    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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    Southold, North Fork 11971
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Parking
    • Patio
    • DVD Player
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    • Housekeeping Included
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Peaceful Year-Round Escape in the Middle of Wine Country It's starting to warm up so come to the North Fork - Sip local wine on the front porch or watch the waves at the private beach which is just a short walk away. Relax and kick back in our 3 bedroom house in Long Island's North Fork. Close...
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    Southold, North Fork 11971
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Shorecrest Beach House, 4 bedroom private beach front, new renovation1 / 32
    (3)Excellent
    Southold
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Washer
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    • Internet Access
    • Air Conditioning
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2018
    We were absolutely blown away by how lovely our stay was at this beach front cottage right on the water in Southold! From the gorgeous sunsets seen from the porch over the water...
    Reviewed July 24, 2018
    This beach house is located right on the north shore of the long island sound, perfectly placed in the middle of the North Fork close to all the beautiful wineries and breweries...
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    About this property
    Newly renovated with two new full bathrooms, new kitchen and second floor bedroom/family room with glorious views overlooking the Long Island Sound, the Shorecrest Beach House has never looked so good! The Shorecrest beach house is located on a grassy bluff overlooking the ocean and available for...
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    Southold, North Fork 11971
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    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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    Southold, North Fork 11971
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Southold
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Ocean Views
    • Porch
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to this idyllic beachfront located directly on the Sound in Southold NY, only 1 hour 45 minutes from NYC. Open-air, camp-style rooms are part of the house's simple charm. Linger over meals with family and friends on the screened-in porch, watch mesmerizing sunsets, swim in the salt water,...
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    Southold, North Fork 11971
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Cable/satellite TV
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    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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    Southold, North Fork 11971
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Southold, a picturesque and unspoiled mecca nestled along the shore of secluded Long Island creek. Located only 5 minutes from the fantastic Greenport with over 50 wineries and incredible restaurants nearby, Long Island is a foodie’s heaven. Walk to the beach from the 2-bedroom,...
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    Southold, North Fork 11971
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    The following rentals are within 10 kilometres of Southold.
    Relaxed Village Farmhouse1 / 17
    (1)Excellent
    Greenport
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Air Conditioning
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    • Washer
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 11, 2018
    Beautiful home in a great location. Very comfortable bedding and areas to relax. The backyard feels like you've been transported to Italy as you sip wine under the grapes...
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    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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    Greenport, North Fork 11944
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Victorian Seasons Stirling1 / 44
    (5)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 July 10, 2018
    I stayed here with two families for a weekend getaway and our jaws dropped when we saw this stunning property. Walking through the door felt like stepping back in time into the...
    Reviewed July 5, 2018
    Amazing stay at Victorian seasons and beautiful hospitality walking distance to Greenport village .. The grounds were breathtaking surrounded by beautiful gardens and amazing...
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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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    Greenport, North Fork 11944
    Holiday Rental House - 5 Bedrooms, 3 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
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 6, 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
    Greenport, North Fork 11944
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    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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    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Cutchogue, North Fork 11935
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Greenport Home w/Furnished Patio - Walk Downtown!1 / 24
    (1)Very good
    Greenport
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 22, 2018
    We booked this for a family Wedding! Was really close to the coast and just a few mins walk to the shops so suited us! Would be good for young families but as we were 7 adults...
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    About this property
    Spend your summer days in Long Island as you relax in 'Jason's Haven,' a 3-bedroom, 1-bathroom vacation rental home that sleeps 6. Nestled within the historical town of Greenport, this home provides a unique New York experience, sans big buildings and bustling sidewalks. Whether you spend your...
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    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Rare Waterfront Experience :: Forever Bay Vistas ::1 / 59
    (2)Excellent
    New Suffolk
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Housekeeping Included
    • Waterfront
    • Washer
    • Grill
    • Patio
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 15, 2018
    This is the most peaceful and beautiful location where the water literally is spread out in front of you from every part of this divine house. The view from the main open plan...
    Reviewed July 9, 2018
    We had a wonderful time, can't wait to go back. Our host were happy to answer all of our questions. We walked to a few resteraunts, the beach and visited some wineries. The...
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    About this property
    Nautical, Waterfront Spa Retreat Setting - Exceptionally Designed New Home This 4-Bedroom, 3.5 Bathroom waterfront home is set in the charming North Fork Village of New Suffolk. Enjoy stunning water views from almost every room in The Houseboat - truly a coastal, spa retreat setting that is one of...
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    New Suffolk, North Fork 11956
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Greenport
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
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    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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    Greenport, North Fork 11944
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    Cutchogue
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    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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    Cutchogue, North Fork 11935
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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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    Greenport, North Fork 11944
    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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    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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    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cutchogue
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Private Garden
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    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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    Cutchogue, North Fork 11935
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Greenport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walking distance to Greenport Village, Sound and Bay Beaches! 1200 sq ft Victorian cottage perfect for a retreat from the heat. Large patio, new kitchen and bath! 1840s historic poet's house, perfect for couples, small family or single seeking reprieve from Manhattan. Original hardwood floors, 2...
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    Greenport, North Fork 11944
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cutchogue
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience Long Island's vibrant North Fork wine country like a local when you stay at this charming 'Vintage Cottage.' Nestled in the sought after beach community of Nassau Point in the heart of wine country, this 4-bedroom, 1.5-bath vacation rental for 10 is the perfect place for your Cutchogue...
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    Cutchogue, North Fork 11935
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater...
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    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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