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Holiday Rentals with Pools in Greenport

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    1 / 14
    5 of 5 bubbles (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 bubbles (33) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4.5 of 5 bubbles (24) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Outdoor Dining Area
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    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... View all property information
    Location Information
    Greenport, North Fork 11944
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    1 / 11
    4 of 5 bubbles (5) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    About this property
    Our one bedroom has 3 rooms + kitchenette. The parlor with convertible couch ( Standerd double ) sleeps two. Our Bedroom has a Queen Size Bed. Porch & Backyard garden. We are just forty yard walk to our block pier. 150 yard walk into town. The heart of Greenport Village. Bay House is on the best... View all property information
    Location Information
    Greenport, North Fork 11944
    5 of 5 bubbles Reviewed 12 July 2016
    So close to everything! The place is in a great spot. Downtown Greenport is a block away and you would never know it. Very quiet and clean space for my wife and I to enjoy our...
    5 of 5 bubbles Reviewed 4 May 2016
    Great location, easy walk to town and right next to a pretty dock. If you travel with 4 you have to walk through the room with fold out bed to reach bathroom so might be better...
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    1 / 25
    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... View all property information
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    Greenport, North Fork 11944
    1 / 22
    4 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
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    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... View all property information
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    Greenport, North Fork 11944
    1 / 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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... View all property information
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    Greenport, North Fork 11944
    1 / 10
    4 of 5 bubbles (1) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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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... View all property information
    Location Information
    Greenport, North Fork 11944
    4 of 5 bubbles Reviewed 7 February 2017
    My family rented this house for the holiday week between Christmas and New Years. The house is located within walking distance to town - which was quite great The house has...
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    1 / 13
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
    Location Information
    Greenport, North Fork 11944
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    1 / 23
    4.5 of 5 bubbles (3) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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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... View all property information
    Location Information
    Greenport, North Fork 11944
    5 of 5 bubbles Reviewed 24 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 just...
    4 of 5 bubbles Reviewed 15 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 few steep...
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    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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... View all property information
    Location Information
    Greenport, North Fork 11944
    1 / 16
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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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 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... View all property information
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    Greenport, North Fork 11944
    1 / 24
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Internet Access
    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    NEW!!! PRIVATE BEACH FRONT HOME - 3 bedroom, 3 bathroom, Walk to town - 1 block RARE! One of a kind opportunity to rent a PRIVATE BEACHFRONT HOME with 250 feet of Sandy Beach! Our newly renovated custom beachfront home has all BRAND NEW FURNISHINGS - NEVER USED BEFORE including mattresses,... View all property information
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    Greenport, North Fork 11944
    1 / 16
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    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... View all property information
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    Greenport, North Fork 11944
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Garden
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    • Pet-friendly
    • Child-friendly
    • x
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    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... View all property information
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    Greenport, North Fork 11944
    1 / 22
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • x
    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... View all property information
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    Greenport, North Fork 11944
    1 / 23
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
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    • x
    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... View all property information
    Location Information
    Greenport, North Fork 11944