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Southold Holiday Rentals

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    Travellers to Southold are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    All 29 Rentals in Southold
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    Waterfront North Fork Sunny Home1 / 25
    (16)Excellent
    Southold
    3 Bedrooms, 1 Bathroom, Sleeps 6 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
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • DVD Player
    • Waterfront
    • Parking
    • Grill
    • Hot Tub
    • Wi-Fi
    • Central Heating
    Suitability
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms 3 Bathroom home for rent. Beautiful landscape and privacy on a full acre with gigantic fenced in backyard with playground. 5 minute walk or 1 minute drive to private community Peconic Bay beach. Excellent condition and comfort. Weber Grill, sun filled deck , quality entertainment system....
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    Southold, North Fork 11971
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Southold
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Satellite TV
    • Secure Parking
    • Grill
    • Private Garden
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large beach front with 5 bedrooms (2 ensuite), 4 living rooms, 3.5 baths This is the perfect home for the extended family vacation, with not only 5 bedrooms, including 2 with ensuite bathrooms but 4 separate sitting/family/den or game rooms plus a pool room! The unique layout offers areas to gather...
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    Southold, North Fork 11971
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Southold
    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 11971
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    • Washer
    • Satellite TV
    • Patio
    • Air Conditioning
    • Porch
    • Grill
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 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 11971
    Holiday Rental House - 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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    Amenities & Details
    • Air Conditioning
    • Grill
    • Porch
    • Satellite TV
    • Patio
    • DVD Player
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 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 18 August 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The following rentals are within 10 kilometres of Southold.
    Cutchogue Beach Cottage1 / 36
    (9)Excellent
    Cutchogue
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Outdoor Dining Area
    • Washer
    • Wi-Fi
    • Grill
    • Patio
    • Central Heating
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2016
    We had a very happy stay here. Contact with Julie was first class, the house is very tastefully decorated and comfortable. It is ideally situated to explore further but has...
    Reviewed 8 August 2016
    We so enjoyed our time here. You really can't find a more homey cottage and the close proximity to the great beach and scenic hilltop playground was tops. Julie was wonderful...
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    About this property
    Cozy Cutchogue Beach Cottage on the North Fork of Long Island. It has 2 bedrooms with queen sized beds and there is a sleeping loft appropriate for children over 9 years old (one queen sized bed and one twin). Deck and backyard with gas grill, outdoor picnic table, fire pit, and tire swing....
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    Cutchogue, North Fork 11935
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 1828 for a ship’s captain, this historic property remains as one of the oldest structures in the village. Original details abound. Large, bright & airy rooms. Brand new furnishings. Perfect for entertaining or a quiet weekend retreat. The Space Located on a tree lined street this...
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    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (7)Excellent
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Balcony
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 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 4 August 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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    The Farmhouse1 / 10
    (1)Very good
    Greenport
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Secure Parking
    • Satellite TV
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 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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    Greenport, North Fork 11944
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Greenport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Greenport, North Fork 11944
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Greenport
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will love this 4 bedroom 4.5 bathroom charmer on a quiet street. Walk to town, shops, carousel LIRR Jitney and ferry to Shelter Island Golf course and beaches 1 mile away. There are over 40 wineries nearby. The front deck has 2 Adirondack chairs to just relax. A full deck off the back over...
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    Greenport, North Fork 11944
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Patio
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    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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    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
    • Satellite TV
    • Grill
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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
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
    • Parking
    • Wi-Fi
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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 11944
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Greenport
    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Parking
    Suitability
    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
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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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
    • 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, 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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    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Greenport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • Internet Access
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the charming seaside village of Greenport from this quaint 1-bedroom, 1-bathroom vacation rental apartment with sleeping accommodations for 2. Only a couple of blocks from downtown, enjoy quick access to numerous restaurants, boutique shops and local attractions. Your ultimate North Fork...
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    Greenport, North Fork 11944
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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 2 September 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 10 June 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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    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
    (33)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 July 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...
    Reviewed 6 August 2014
    Enjoyed four night stay .condo unit &entire complex was clean and well maintained.Location was perfect for touring vineyards ,Shelter Island and Greenport attractions.Pool...
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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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    Family and Friends in Greenport1 / 23
    (3)Very good
    Greenport
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • Housekeeping Included
    • DVD Player
    • Balcony
    • Satellite TV
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 September 2014
    The pictures of this house do not do it justice. It is spacious although an older home, with wide floorboards, a great room with fireplace, toys for kids, deck for eating or...
    Reviewed 14 October 2013
    We just returned from renting for Columbus weekend. Very happy with the house. We needed a ground floor room & shower for my 88yr old Mother & this worked out perfect. A...
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    About this property
    Our house is an historic Dutch colonial, both cozy and spacious, with warm wood trim and wood floors throughout. The 20 x 20ft. Great Room, a perfect gathering space for family and friends is complete with a baby grand piano, cable TV, children's toys and books, classic novels and wood burning...
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    Location Information
    Greenport, North Fork 11944
    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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    • Outdoor Dining Area
    • Wi-Fi
    • Patio
    • Parking
    • 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 11944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Greenport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
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    • Private Garden
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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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    Location Information
    Greenport, North Fork 11944
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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