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Shelter Island Heights House Rentals

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    Don't let other travellers get your favourite Shelter Island Heights area holiday home. You're so close to securing your perfect getaway. Book today.
    25 Matching Rentals in the Shelter Island Heights AreaView all 40 rentals
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    The following rentals are within 10 kilometres of Shelter Island Heights.
    North Fork House with Private Beach Access1 / 14
    (5)Excellent
    East Marion, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    CHARMING ONE-BEDROOM EFFICIENCY APARTMENT IN THE HEART OF EAST MARION1 / 21
    (1)Excellent
    East Marion, NY
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES1 / 17
    (2)Excellent
    Southold, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Greenport, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • 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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    Southold, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Balcony
    • Patio
    • Grill
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Greenport, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Pet friendly
    Kid friendly
    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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    Southold, NY
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Cable/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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    East Marion, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated 1905 North Fork farmhouse comes with lots of light, clean lines, and deeded beach access. A new gourmet kitchen, back deck, and large fenced in backyard make it ideal for entertaining, barbecuing, or spending a lazy afternoon in the summer hammock. Use the house as a base to...
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    East Marion, North Fork 11939
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    The Farmhouse1 / 15
    (1)Very good
    Greenport, NY
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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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    Victorian Seasons Stirling1 / 28
    (2)Excellent
    Greenport, NY
    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2018
    A group of childhood girlfriends looking for a getaway and one of my girlfriends took care of all the arrangements. We arrived Friday afternoon to a warm welcome tour by the...
    Reviewed 12 March 2018
    Stirling is a beautiful Victorian home meticulously restored to it's original glory. The hosts are gracious and attentive to all guest needs. The interior spaces are stunning...
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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...
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    Greenport, North Fork 11944
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    East Marion, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renovated Waterfront Cottage with private beach and spectacular views! The house sits on the edge of the bluff with views of a secluded cove on the sound and has access to an infinity deck where you can relax and enjoy the water views, the sunsets, the landscaped garden and the birdlife all around...
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    East Marion, North Fork 11939
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Southold, NY
    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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    Greenport, NY
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
    • Parking
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend your summer days in Long Island as you relax in 'Jason's Haven,' a 3-bedroom, 1-bathroom vacation rental home that sleeps 6. Nestled within the historical town of Greenport, this home provides a unique New York experience, sans big buildings and bustling sidewalks. Whether you spend your...
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    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Greenport, NY
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
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    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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    Orient, NY
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Parking
    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For a rejuvenating, fantastical getaway from the day-to-day doldrums, this gorgeous waterfront home is waiting at the very end of rustic Windward Road for you. With four main bedrooms, and a completely furnished attic that can serve as room for even more, you can bring your whole family for a...
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    Orient, North Fork 11957
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Southold, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Secure Parking
    • Private Garden
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    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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    Greenport, NY
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
    • Cable/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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    East Marion, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Originally built in the late 1800s this lovely house is in the center of our quaint town of East Marion. We are just two miles from Greenport, a bustling port town, where you can catch the Shelter Island Ferry or the last stop on the LIRR, and just 4 miles from Orient and the Cross-Sound Ferry to...
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    East Marion, North Fork 11939
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Southold, NY
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Ocean Views
    • Porch
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Waterfront
    Suitability
    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
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    East Marion, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Parking
    • Patio
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On your next visit to the Hamptons area, be sure to secure this updated and relaxing retreat in the heart of East Marion. This classic Cape Cod 3-bedroom, 2.5-bathroom vacation rental home accommodates up to 8 travelers, and sits within walking distance to a secluded beach and community park with...
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    East Marion, North Fork 11939
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Southold, NY
    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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    East Marion, NY
    5 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Victorian Seasons Main House, nestled between wildlife preserves and protected land. Victorian Seasons is a significantly important historic site that dates back to 1855. It is on the historic corridor in the heart of East Marion on the beautiful North Fork of Long Island. This...
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    East Marion, North Fork 11939
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 9
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    Greenport, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated ranch private home with spacious deck, large teak dining set, new grill, CAC, washer/dryer, front porch, fully equipped kitchen, wall mounted flat screen TVs in every bedroom and family room, farm dining room table. Nicely appointed home within walking distance to gorgeous private...
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    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Greenport, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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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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    Greenport, North Fork 11944
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Southold, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Ocean Views
    • Washer
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    near beach 3 Bedrooms and 1.5 baths Plus and outdoor shower, nice yard,WiFi,bbq Begin Description: Awesome Beach House (less than 50 yards [30 second walk to the beach] from private sandy bay beach) location location location This House was built in the 1700's (revolutionary era) and has been...
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    Southold, North Fork 11971
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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