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Holiday Rentals in Shelter Island, NY

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    ₹ 37,537 Average
    ₹ 67,000+
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    Travellers to Shelter Island are booking August dates now. Secure your holiday home today, and have the perfect trip.
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    4 of 5 stars (1) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Private Garden
    • Internet Access
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    About this property
    Beautiful 1875 Historic Shelter Island Heights Gingerbread Victorian Home: Rental includes: Two kayaks, Tennis Court, Shelter Island Heights Private Beach Club Use (private beach, picnic area, playground, showers, cabanas) for you and your family Details: 4 bedrooms (we have two master bedrooms... View all property information
    Location Information
    Shelter Island, Hamptons 11965
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Large Shelter Island Farmhouse<BR>Beautiful Shelter Island is the most enjoyable, preserved, natural beauty on the North Fork and is yours to explore. Relaxing is mandatory...<BR>The farmhouse is close to all - steps from the golf course and beach<BR>46 West Neck Road - overlooks Town Golf Course+... View all property information
    Location Information
    Shelter Island, Hamptons 11965
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Outdoor Dining Area
    • Terrace
    • Wi-Fi
    • Grill
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    • Private Outdoor...
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    Tennis Court, Swimming Pool, Bocci, Soccer Lawn, Luxury Shelter Island 3-Bedroom<BR>Located in what is arguably the most desirable part of the island, this house appeals to guests who are looking for clean, modern, and stylish accomodations in a picturesque setting. Huge open kitchen with Sub-zero... View all property information
    Location Information
    Shelter Island, Hamptons 11964
    Private Room, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    About Seven Newly renovated in 2014, SEVEN bed and breakfast offers a selection guest rooms for various combinations of guests, with king, queen, double queen and double twin rooms. Each guestroom includes air conditioning, a flat screen television, light seasonal goose down comforters, 100%... View all property information
    Location Information
    Shelter Island, Hamptons 11965
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Located on Shelter Island, NY down a quiet lane within walking distance of Wades Beach and the Nature Conservancy's Mashomack preserve. This impeccably maintained hilltop traditional, reminiscent of a European country home, is situated on 2 acres. Entering the front foyer, your eye will be drawn... View all property information
    Location Information
    Shelter Island, Hamptons 11964
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Escape to a private pastoral compound comprised of a historical home and a guest carriage house sitting on eight lush acres. The main country manor house offers three spacious bedrooms, including an en suite master with an attached private office, 2.5 baths, living, dining, entertaining spaces and... View all property information
    Location Information
    Shelter Island, Hamptons 11965
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Washer
    • Patio
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This charming and newly renovated 3 bedroom, 2 bath ranch style home is located on a quiet street close to both Sunset and Shell beaches and within walking distance to Silver Beach off of Bootleggers Alley. We have bikes on hand to help you reach these and other beautiful destinations around... View all property information
    Location Information
    Shelter Island, Hamptons 11964
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Grill
    • Satellite TV
    • Private Outdoor...
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This eclectic 'Round' house is a one of a kind on Shelter Island. Sited on 1.5 acres in Hay Beach with slices of bay views, this upside down house offers 4 Bedrooms and 2 Baths on the ground floor with an open layout upstairs which includes the living and dining room, kitchen, ½ bath, and covered... View all property information
    Location Information
    Shelter Island, Hamptons 11965