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Greenport Condos

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    Travelers to Greenport are booking September dates now. Secure your vacation rental today, and have the perfect trip.
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    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Farmhouse1 / 10
    (1)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    New North Fork Beach Condo, Pool, Resort, Heart of the Wineries1 / 12
    (24)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
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    • 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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    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Private Yard
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will love this 4 bedroom 4.5 bathroom charmer on a quiet street. Walk to town, shops, carousel LIRR Jitney and ferry to Shelter Island Golf course and beaches 1 mile away. There are over 40 wineries nearby. The front deck has 2 Adirondack chairs to just relax. A full deck off the back over...
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    Greenport, North Fork 11944
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    Cliffside Resort Greenport Luxurious Waterfront Condo- with Pool!1 / 8
    (33)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Terrace
    • Internet Access
    • Satellite TV
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed August 6, 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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    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Yard
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
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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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    Greenport, North Fork 11944
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    Family and Friends in Greenport1 / 23
    (3)Very good
    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 September 23, 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 October 14, 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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    Greenport, North Fork 11944
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Yard
    • Parking
    • Air Conditioning
    • 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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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    Location Information
    Greenport, North Fork 11944
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    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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    Location Information
    Greenport, North Fork 11944
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Patio
    • Internet Access
    • Parking
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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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
    • Wi-Fi
    • Private Yard
    • Air Conditioning
    • Secure Parking
    Suitability
    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Patio
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Greenport, North Fork 11944
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Historic Captain's House in Greenport Village1 / 24
    (12)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Internet Access
    • Satellite TV
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    • Grill
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    Pet friendly
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    Smoking allowed
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    Greenport, North Fork 11944
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • Washer
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Greenport, North Fork 11944
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Dreamlike Property In Greenport - Beach Chill Beyond Compare + Near to Vineyards1 / 24
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Central Heating
    • Internet Access
    • Satellite TV
    • Washer
    • Parking
    • Housekeeping Included
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Greenport, North Fork 11944
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    The Farmhouse on Front Street1 / 23
    (12)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    • Balcony
    • Terrace
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Greenport, North Fork 11944
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    1873 Beautiful Victorian home in the heart of Greenport, New York1 / 22
    (14)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
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    • Grill
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    Pet friendly
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    Smoking allowed
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    Greenport, North Fork 10017
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Historic 1830 Captain's home garden wing, huge private garden, walk to all!1 / 23
    (19)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
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    Greenport, North Fork 11944
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Convient and safe home surrounded by water and beautiful villages1 / 20
    (20)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Greenport, North Fork 11944
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    Charming Farmhouse on the beautiful Long Island North Fork1 / 24
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Greenport, North Fork 11944
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Restored Seaport Home1 / 22
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Greenport, North Fork 11944
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charming Summer Cottage Rental Close to Beach & Town1 / 6
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Greenport, North Fork 11944
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Charming And Spacious Five Room Suite..Steps To Bay Beach ,Stroll To Village1 / 24
    (32)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Greenport, North Fork 11944
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 4
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    Your Secluded Sanctuary In The Heart Of The North Fork1 / 20
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Greenport, North Fork 11944
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1820 Whaling Captain's Home1 / 23
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Greenport, North Fork 11944
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 5
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    Family And Pet Friendly 3 Bed+, 1.5 Bath Lovely Victorian Former Schoolhouse1 / 19
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Greenport, North Fork 11944
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Relax to a Unique Vineyard View1 / 23
    (31)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    Greenport, North Fork 11944
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Renovated Farm House1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Greenport, North Fork 11944
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Art Lovers Lair in Historic Greenport  Building1 / 8
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
    • Satellite TV
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    Pet friendly
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    Greenport, North Fork 11944
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Greenport, North Fork 11944
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Studio Retreat Walking Distance From Everything In Greenport Village...1 / 13
    (4)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Greenport, North Fork 11944
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Beautiful Home - Greenport Getaway1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Private Outdoor Pool (Unheated)
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    Greenport, North Fork 11944
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Historic 1830s Greenport Home1 / 24
    (10)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Greenport, North Fork 11944
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Greenport Soundfront Estate1 / 23
    (4)Excellent
    8 Bedrooms, 8 Bathrooms, Sleeps 15 Quick View
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    • Washer
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    • Hot Tub
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    Greenport, North Fork 11944
    Rental Home - 8 Bedrooms, 8 Bathrooms, Sleeps 15
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    Cleves Point Estates Home, Private sandy beach1 / 17
    (7)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Greenport, North Fork 11944
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views1 / 14
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Satellite TV
    • Washer
    • DVD Player
    • Shared Indoor Pool
    • Air Conditioning
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spacious Historic Downtown Greenport Apartment1 / 21
    (15)Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Greenport, North Fork 11944
    Condo/Apartment - 6 Bedrooms, 2 Bathrooms, Sleeps 12
    Make Inquiry
    Greenport Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers
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    74° 57°
    August
    68° 48°
    September
    57° 37°
    October
    47° 29°
    November

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