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Southold House Rentals

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    Travellers to Southold are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    22 Matching Rentals in the Southold AreaView all 38 rentals
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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
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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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
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    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
    5 Bedrooms, 4 Bathrooms, Sleeps 14 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 14
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    Southold
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Washer
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    • Internet Access
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    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 8
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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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    Southold, North Fork 11971
    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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    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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    The following rentals are within 10 kilometres of Southold.
    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
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Private Garden
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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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    Greenport
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
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    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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    Greenport, North Fork 11944
    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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    Suitability
    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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    Greenport, North Fork 11944
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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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
    Greenport, North Fork 11944
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Victorian Seasons Stirling1 / 32
    (2)Excellent
    Greenport
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 13 March 2018
    Stirling is a beautiful Victorian home meticulously restored to it's original glory. The hosts are gracious and attentive to all guest needs. The interior spaces are stunning...
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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
    Greenport, North Fork 11944
    Holiday Rental House - 5 Bedrooms, 3 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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    Cutchogue, North Fork 11935
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Greenport
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
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    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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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    Greenport, North Fork 11944
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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
    • 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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    Cutchogue, North Fork 11935
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cutchogue
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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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
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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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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