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Southold Vacation Rentals

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    Travelers to Southold are booking April dates now. Secure your vacation rental today, and have the perfect trip.
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    Southold
    5 Bedrooms, 4 Bathrooms, Sleeps 14 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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    Beach House In Wine Country; Huge Sun Room1 / 16
    (2)Excellent
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
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    Pet friendly
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    Smoking allowed
    About this property
    Cottage w/ Beaches, 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 - Let me know your Weeks !! Labor Day Weekend...
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    Southold, North Fork 11971
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Adorable, Renovated 1890's Farmhouse... Walk to Beaches & Town!1 / 23
    (9)Excellent
    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Porch
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    Pet friendly
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    Reviewed July 1, 2015
    My husband and I just stayed in this beautiful house with two friends who are a couple. The photos of the house on this site are accurate and, for once, we were not at all...
    Reviewed August 18, 2013
    This is a beautiful, well maintained house· Decorated and furnished to a very high standard. Fantastically situated for the beach in the lovely town of Southold.We used for our...
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    About this property
    This charming farmhouse is just what you’ve been looking for: A beautiful, newly renovated 1890's house with all the modern conveniences, perfectly located a few short blocks to Founders Landing Beach Park, Town Beach and Southold Village. About the House The house is a very bright and airy,...
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Southold
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    • Hot Tub
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    Pet friendly
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    About this property
    [New listing here, but we have reviews on the other vacation rental sites] Large, airy, split level, four bedroom home that is perfect for a East End getaway. Located just down the road from beaches and less than a mile from the nearest winery, our home offers a great base from which to explore all...
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    Southold, North Fork 11971
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
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    Pet friendly
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • DVD Player
    • Waterfront
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique country cottage is situated on a spring-fed fresh water lake one block from Kenney's Beach - a sandy Long Island Sound beach staffed by Southold Town lifeguards. Designed to maximize the beauty of its pristine surroundings, the entire back of the house has French doors opening onto a...
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    Southold, North Fork 11971
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Southold
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Ocean Views
    • Porch
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    • Waterfront
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    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
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Private Yard
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    Pet friendly
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    Smoking allowed
    About this property
    Families will love the location of this two bedroom spacious country home just a short walk to a private sandy Shelter Bay beach along a quiet country dead end road, so no through traffic and safe for bicycling, children and walking the family pet. We are glad to be able to welcome your dog, as we...
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    Southold, North Fork 11971
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Southold Soundfront Private Beach1 / 19
    (9)Very good
    Southold
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 4
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    Cute Cottage Apartment Near town, beaches and vineyards (WBH)1 / 15
    (2)Excellent
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Southold, North Fork 11971
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Huge 6 Bedroom Home With Pool, Close To Beach and Wineries, Central A/C1 / 24
    (1)Excellent
    Southold
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Unheated)
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    Southold, North Fork 11971
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Southold
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Southold, North Fork 11971
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beautifully Renovated Farmhouse with Gunite Saltwater Pool, 1/2 Mile to Beach1 / 22
    (4)Excellent
    Southold
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    SOUTHOLD COTTAGE - Fully-Renovated One-Bedroom Cottage1 / 14
    (5)Excellent
    Southold
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Southold, North Fork 11971
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Southold
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Southold, North Fork 11971
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Southold, NY- Heart of North Fork Wine Country1 / 17
    (2)Very good
    Southold
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Southold, North Fork 11971
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Escape to the North Fork this Summer- Cozy Cottage - Private Beach Down the Road1 / 21
    (1)Very good
    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beachfront home on the North Fork1 / 22
    (2)Excellent
    Southold
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Beautiful NEW Waterfront Paradise In Southold1 / 24
    (4)Excellent
    Southold
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Southold, North Fork 11971
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Spacious Entertainer's Dream Home Close to Wineries/Beaches, Featured on HGTV1 / 24
    (19)Excellent
    Southold
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Southold, North Fork 11971
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Entertainers Delight Just Steps From The Beach1 / 24
    (6)Excellent
    Southold
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Patio
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    Southold, North Fork 11971
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    2 Bedroom Apartment in Historic Home with private yard (WBH)1 / 20
    (18)Very good
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Southold, North Fork 11971
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Newly Renovated North Fork Beach & Wine Country Home1 / 17
    (4)Very good
    Southold
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Southold, North Fork 11971
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Southold. Immaculate 3 BR 2 bath ranch 180' to private beach1 / 15
    (2)Very good
    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Southold
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Southold, North Fork 11971
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Perfect Family Vacation Home! Charming Waterfront Property close to Vineyards1 / 24
    (10)Excellent
    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Waterfront Colonial with Dock for boat or kayaks1 / 23
    (11)Excellent
    Southold
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Southold, North Fork 11971
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    North Fork Beach House1 / 17
    (1)Excellent
    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Renovated Cottage in Private North Fork Beach Community  - LABOR DAY AVAILABLE!!1 / 9
    (6)Excellent
    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Great Location 2 Blocks from Private Beach!1 / 16
    (1)Excellent
    Southold
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Southold, North Fork 11971
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Lakefront Beach Home/Walk to Kenney's Beach1 / 13
    (1)Excellent
    Southold
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    The following rentals are within 5 miles of Southold.
    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (9)Excellent
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Reviewed October 15, 2016
    That's it! Unit was clean and comfortable. Beach was right there. Drive to town or spots of interest easily. Compact, well organized, nice little terrace overlooking the water...
    Reviewed August 4, 2016
    The condo was very comfortable. Greenport is a great town with lots of restaurants and shops.There are many vineyards right in the area and you couldn't get any easier access to...
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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 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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
    Rental Home - 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
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
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    Pet friendly
    Kid friendly
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    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
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Cutchogue Beach Cottage1 / 18
    (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
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    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 23, 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 August 8, 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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    Cutchogue, North Fork 11935
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Greenport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    About this property
    Explore the historic seaport of Greenport Village from this recently remodeled 1-bedroom, 1-bathroom vacation rental apartment that comfortably sleeps 2. Located in the heart of downtown, you won’t find a better location to explore all the area has to offer than from this charming apartment. Only 2...
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    Location Information
    Greenport, North Fork 11944
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Location Information
    Cutchogue, North Fork 11935
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Greenport
    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elegant and especially designed and built for one of the wealthiest bankers on the North Fork. Situated on enormous 3/4 acre property in the most prestigious setting of the National Historic District in Greenport Village. Lovingly restored to its original elegance and authentic Classic Queen...
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    Location Information
    Greenport, North Fork 11944
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    Greenport
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Private Yard
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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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    Location Information
    Greenport, North Fork 11944
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    Peconic
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Parking
    • Grill
    • Housekeeping Included
    • Air Conditioning
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enter a world of tranquility and surround yourself with the beauty of nature!<BR>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...
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    Peconic, North Fork 11958
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    New North Fork Beach Condo, Pool, Resort, Heart of the Wineries1 / 12
    (24)Very good
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Internet Access
    • Terrace
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 2, 2014
    6 Girlfriends with children wanted a quick easy trip with no traffic to end the summer. We got exactly that! The Cliffside Resort was perfect. I honestly can't say what I...
    Reviewed June 10, 2014
    My son got married this past weekend at a Vineyard near Cliffside and my family, the bride's family and some guests spent the weekend there. In total, we rented about 23 units...
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    About this property
    Beautiful 2 Bedroom 2 Bathroom Poolside Unit. All that Cliffside Resort and the Sound have to offer are just steps away. Additional amenities include: close to town, in-room entertainment system, kitchenette, private walkway to the sound, refrigerated wine cooler, on sound, washer & dryer...
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    Location Information
    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cliffside Resort Greenport Luxurious Waterfront Condo- with Pool!1 / 8
    (34)Excellent
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Terrace
    • Internet Access
    • Satellite TV
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Needed a place for a quick trip to north fork . Found this place. Only stayed 1 night but it was clean, comfortable & had two bathrooms - for three women that is a must...
    Reviewed July 2, 2015
    My college friends & I have been coming here for @ 6 years...nowhere better....the condo is clean and nicely decorated......if you choose water view/front...well worth the...
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    About this property
    As featured by New York Magazine, the Cliffside Resort entertains the perfect vacation! This 68 unit complex, located directly on the Long Island Sound with incredible sunset views, offers brand new 2 bedroom 2 bathroom luxurious accommodations. Cliffside Resort Waterfront Condominiums at...
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    Location Information
    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the scenic seaside village of Greenport in this 2-bedroom, 2-bathroom vacation rental apartment that comfortably sleeps 4. Located in the heart of Greenport Village, enjoy quick access to fine restaurants, exceptional shopping and numerous local attractions. Boasting 1,850 square-feet of...
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    Location Information
    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Greenport
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Air Conditioning
    • Balcony
    • Porch
    • Wi-Fi
    • 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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    Location Information
    Greenport, North Fork 11944
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
    • Parking
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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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    Location Information
    Greenport, North Fork 11944
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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