Comprised of land, marsh, and mist, Shelter Island is nestled between the North and South Forks of Long Island, perfect for a retreat in Shelter Island vacation rentals. A popular summer resort with charming Shelter Island rentals, this tiny town is accessed by a busy ferry system, and has four public beaches and two golf courses. The simplicity of the area makes way for pure relaxation in this natural reserve, including catching winks in your Shelter Island vacation rental. Beautiful lighthouses, majestic windmills, pristine shorelines, and mesmerizing boat activity are fantastic sights to see here, and you'll find all of them near your Shelter Island rental for a relaxing vacation.
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Shelter Island Vacation Rentals
Shelter Island Vacation Rentals - Search Over 250,000 Listings
| Featured Rentals | Type | Beds | Baths | Sleeps | Rate | |
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Sag Harbor Summer Rental by the Bay - Sag HarborAmenities:Beach, Ski, Golf Course, Pool, Kitchen, Dishwasher, Washer/Dryer, TV Description:Centrally located in the Hamptons, and just a couple minutes ?? walk to Private Beach on the bay in Sag Harbor, five minutes drive to Sag Main Beach, and 10 minutes to South or East Hampton. This home is great for entertaining with a gas grill, large kitchen with dining area and living room. Also, large family room equipped with big screen TV. All bedrooms have TV ??s and the home sleeps 8. |
House |
3 Beds |
2 Baths |
8 People |
$25 - $257 |
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Beautiful Country House - Shelter IslandAmenities:Beach, Ski, Golf Course, Pool, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:New house with modern conveniences |
House |
3 Beds |
2.5 Baths |
6 People |
$167 - $429 |
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Waterfront house set in Nature Preserve - Shelter IslandAmenities:Beach, Ski, Kitchen, Dishwasher, Washer/Dryer, TV Description:Water Front house set in a nature preserve on Ram Island, Shelter Island over looking picturesque Coecles Harbour. |
House |
4 Beds |
3 Baths |
8 People |
$143 - $429 |
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Waterview: September/October are Beautiful here! - Shelter IslandAmenities:Beach, Golf Course, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:this newly renovated victorian -with exquisite attention to detail and fixtures - is located in the historic district of shelter island heights. within walking distance to the north ferry (and greenport, with train/bus service to nyc) and the town of shelter island heights. this summer home features a wide wrap-around front porch with water view, and comes with membership to the heights beach and tennis club, a five minute walk. |
House |
4 Beds |
2.5 Baths |
6 People |
$400 - $400 |
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Skaneateles - Skaneateles LakeAmenities:Beach, Ski, Golf Course, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:Beautiful Skaneateles Lake view house. Furnished 3 bedrooms, 2 bathrooms, newly remodeled kitchen with all new stainless steel appliances, garage, large yard, deck and wrap around porch. Conveniently located near the Skaneateles boat launch and marina. |
House |
3 Beds |
3 Baths |
5 People |
$113 - $113 |
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Waterfront Summer Getaway - Sound BeachAmenities:Beach, Kitchen, Dishwasher, Washer/Dryer, Pets OK, TV Description:Charming summer home with breathtaking water views. Steps from the beach; enjoy kayaking, windsurfing, fishing, swimming and long walks along the spectacular seashore. Summer house located on the bluff with amazing views of the Long Island Sound. Currently availability is from June 1 through July 15. 1:15 min drive (60 miles) from Manhattan. |
House |
2 Beds |
2.5 Baths |
5 People |
$171 - $225 |
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Shelter Island - >>> ROMANTIC Beach Getaway! Seclusion, WaterfallsAmenities:Beach, Ski, Golf Course, Pool, Hot Tub, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, Pets OK, TV Description:This Shelter Island Hamptons Long Island NY is quite possibly the most Romantic Hideaway Vacation Rental available in the Hampton's NY area. Directly across the street from the waterfront, the sound and smells of water abound. Relax while you are surrounded by the myriad sounds of all our water features including, multiple waterfalls, fountains, pools and the waves. |
House |
2 Beds |
1.5 Baths |
4 People |
$242 - $429 |
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Waterfront with View, Dock - Saranac LakeAmenities:Beach, Ski, Golf Course, Pool, Kitchen, Dishwasher, Pets OK, TV Description:Fabulous Home on Lake Flower with floating raft. Enjoy the large yard or over sized deck. Enjoy your morning coffee in the solarium overlooking waterfront view ---beautiful in any season. Enjoy the fire in either the living room or dining room and quiet in the Library. Great for family vacations or with friends. |
House |
3 Beds |
2 Baths |
8 People |
$343 - $365 |
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3BR home, 3 blocks from the track, - Saratoga SpringsAmenities:Golf Course, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:Just dropped the rate on our last available week for track season 7/27-8/3, just $1500 (less than $250/night!) Will also consider $250/night, 3-night min. Forget the hassles of traffic and parking on race day, just tuck 'the form' under your arm and stroll to the track. Only three blocks to the track entrance, and a short walk through Congress Park to Broadway. |
House |
3 Beds |
2 Baths |
6 People |
$214 - $250 |
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Shelter Island - ->>>HAMPTONS - Shelter Island NY -Euro Beach HomeAmenities:Beach, Ski, Golf Course, Pool, Hot Tub, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, Pets OK, TV Description:Located across street from waterfront, Our new Beach Vacation Home Rental is on the exclusive Shelter Island, 'The Jewel of The Hampton's in the Estate Section. European Elegance and influence abounds in this custom Vacation Home rental. |
House |
3 Beds |
3 Baths |
8 People |
$177 - $929 |
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