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Vacation Rentals near The Old Field Vineyards

59600 New York 25, Southold, New York 11971
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    Travelers to Southold are booking April dates now. Secure your vacation rental today, and have the perfect trip.
    27 Matching Rentals in the Southold AreaView all 31 rentals
    PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES1 / 17
    (2)Excellent
    Southold
    2.0 miles from The Old Field Vineyards
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Beautiful Classic North Fork Home, wrap around porch, pool, walk to beach1 / 19
    (1)Excellent
    Southold
    2.1 miles from The Old Field Vineyards
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Southold
    1.1 miles from The Old Field Vineyards
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Beach House In Wine Country; walk to beach, large sun room, outdoor dining1 / 16
    (2)Excellent
    Southold
    1.6 miles from The Old Field Vineyards
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Porch
    • Grill
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 3, 2015
    An absolutely stunning and beautiful home. Clean, comfortable, fully updated, this house is perfect for peace and relaxation. The bright and spacious sun room is perfect for...
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    About this property
    Walk to our private beach just houses away, kick back with a local bottle of pinot in our beautiful sunroom, barbecue in the backyard or cook your favorites in our new kitchen and dine al fresco on the patio, dining room or eat at the counter and entertain the cook. We provide 2 comfortable...
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    Southold, North Fork
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Shorecrest Beach House, 4 bedroom private beach front, new renovation1 / 32
    (3)Excellent
    Southold
    1.3 miles from The Old Field Vineyards
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Waterfront
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    • 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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Southold
    1.2 miles from The Old Field Vineyards
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Ocean Views
    • Porch
    • Grill
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    • 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
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Southold
    0.6 miles from The Old Field Vineyards
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Grill
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Southold, NY Beach Cottage, Walk to Beautiful Founders Landing Beach, Farm Stands, Wine, Shopping, Let us know your dates! BI - Weekly Rental - Bring the Dog(s) & Work Here! WIFI & CABLE Beautiful Restful Retreat! Come experience award-winning wineries, antique shops, art galleries, Summer 2017...
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    Southold, North Fork
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Southold
    2.7 miles from The Old Field Vineyards
    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Southold
    2.7 miles from The Old Field Vineyards
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Southold
    1.8 miles from The Old Field Vineyards
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Parking
    • Patio
    • DVD Player
    • Grill
    • 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Southold
    0.1 miles from The Old Field Vineyards
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The following rentals are within 5 miles of Southold.
    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (11)Excellent
    Greenport
    2.3 miles from The Old Field Vineyards
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Waterfront
    • Wi-Fi
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    • Cable/satellite TV
    • Balcony
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 5, 2018
    Very nice, spacious apartment. Tranquil surroundings. Small pebble stone beach with a serene atmosphere. Beautiful sunsets. Very bucolic. Communication with the owner was...
    Reviewed February 11, 2018
    Great accommodations, beautiful view, FANTASTIC SUNSETS, what’s not to like!As a repeat customer staying here in Spring, Summer and Fall I give stars.
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    About this property
    Overview: Waterfront Water's Edge suite, Suite C-204, accommodates up to 6 guests (see below) with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. Quoted rental rates include all taxes, I do not charge resort fees...
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    Greenport, North Fork
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Shelter Island Heights
    3.5 miles from The Old Field Vineyards
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Yard
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated with top of the line furniture, this house is close to: world renown Sunset Beach restaurant by famed owner Andre Balazs, Commander Cody's, Marie Eiffel Dockside Market, Mashomack Preserve, Salt Restaurant, Sylvestor Manor, Gardeners Bay country club, Shelter Island Heights, and the...
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    Shelter Island Heights, Shelter Island
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Farmhouse1 / 15
    (1)Very good
    Greenport
    2.9 miles from The Old Field Vineyards
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Secure Parking
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    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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    Greenport, North Fork
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Greenport
    3.4 miles from The Old Field Vineyards
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Private Yard
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    • 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
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    Victorian Seasons Stirling1 / 88
    (5)Excellent
    Greenport
    3.5 miles from The Old Field Vineyards
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Yard
    • Wi-Fi
    • Air Conditioning
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    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
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    North Fork Beach House on LI Sound1 / 14
    (1)Excellent
    Peconic
    3.7 miles from The Old Field Vineyards
    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 April 27, 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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    Peconic, North Fork
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Relaxed Village Farmhouse1 / 17
    (1)Excellent
    Greenport
    3.5 miles from The Old Field Vineyards
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
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    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Greenport
    3.2 miles from The Old Field Vineyards
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Greenport
    3.7 miles from The Old Field Vineyards
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
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    • Balcony
    • Porch
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    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Entirely renovated, spacious and quiet farmhouse two blocks from the marina, and a 5 minute bike ride to the beach or town. With original hardwood floors, modern kitchen with Viking appliances, two fireplaces, grill, and al fresco dining under a pergola. Located in Greenport, NY, the middle of wine...
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    Greenport, North Fork
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Greenport
    3.5 miles from The Old Field Vineyards
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic Greenport Village has been recently renovated and is in walking distance to all. This is a 2 family home that can be rented separately or together. Pricing here is for house 2. One bedroom has a queen and the other can be configured as a king or two twins. Parking, beach access, convenient...
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    Greenport, North Fork
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Cutchogue
    4.3 miles from The Old Field Vineyards
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Private Yard
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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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Greenport
    3.4 miles from The Old Field Vineyards
    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Shelter Island Heights
    2.2 miles from The Old Field Vineyards
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Grill
    • Hot Tub
    • Patio
    • Terrace
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    55 Shore is a spectacular waterfront villa on Shelter Island, just a short walk from Sunset Beach and its stylish hotel. Enjoying panoramic bay and sunset views and a private beach with two boat docks, the 7,500 square-foot villa features beautiful alfresco living areas, exquisite interior spaces,...
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    Shelter Island Heights, Shelter Island
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Greenport
    3.5 miles from The Old Field Vineyards
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Outdoor Dining Area
    • Wi-Fi
    • Patio
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    • Grill
    • Children's Pool
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic home in Greenport Village walking distance to restaurants, water, shopping etc..bike or short drive from vineyards. Large yard with outdoor patio with BBQ and outdoor shower. 2 family home with two separate duplex units that can be rented separately or together. Perfect for family...
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    Greenport, North Fork
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Greenport
    3.2 miles from The Old Field Vineyards
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Greenport
    3.6 miles from The Old Field Vineyards
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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