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Holiday Rentals in Greenport

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    ₹ 24,740 Average
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    ₹ 0₹ 64,000+
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    Travellers to Greenport are booking May dates now. Secure your holiday home today, and have the perfect trip.
    All 15 Rentals in Greenport
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    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    The Farmhouse1 / 15
    (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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    • Wi-Fi
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    • Private Garden
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    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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Patio
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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
    • 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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    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
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    • Cable/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
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Garden
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    • 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
    • Cable/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
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Air Conditioning
    • Internet Access
    • Patio
    Suitability
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
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    Suitability
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    1903 Village Farmhouse, full of character, light and air. A place to relax, unwind and drink wine on the front porch, say hello to our neighbors or take an afternoon nap. Walk into the village for shopping and dinner or ride your bike to the beach. Visit one of the many local wineries and stop...
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    Greenport, North Fork 11944
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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