Search Holiday Rentals in Shelter Island

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Top Holiday Rentals in Shelter Island

Front of property – evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1018)
"The hotel was beautiful. Town is very close by and they offer a shuttle service to take you around. It's nice overall."
The price is ₹14,028
per night
28 May - 29 May
Montauk Manor
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (181)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is ₹20,541
per night
14 May - 15 May
Cliffside Resort Condominiums
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (234)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is ₹12,835
per night
14 May - 15 May
Windward Shores Ocean Resort
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Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (184)
"Every room in the hotel has a little garden in the backyard which is linked with the park, it’s super natural and quiet and definitely worth to stay"
The price is ₹13,567
per night
2 Jun - 3 Jun
Driftwood Resort
On the beach, white sand
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (219)
"Very nice location and nice condo"
The price is ₹18,693
per night
28 May - 29 May
The Surf Club
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (295)
"We enjoyed our stay!"
The price is ₹13,660
per night
30 May - 31 May
Montauk Oceanside Suites
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Shelter Island you may be interested in

Front of property – evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1018)
"The hotel was beautiful. Town is very close by and they offer a shuttle service to take you around. It's nice overall."
The price is ₹14,028
per night
28 May - 29 May
Montauk Manor
Indoor pool, outdoor pool
Hyatt Place Long Island East End
3.0 star property
9.0 out of 10, Wonderful, (1004)
"."
The price is ₹12,700
per night
19 May - 20 May
Hyatt Place Long Island East End
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very good, (564)
"front desk staff irritating as can be "
The price is ₹43,962
per night
29 May - 30 May
Gurney's Montauk Resort & Seawater Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find holiday rentals in Shelter Island?

Yes, there are holiday rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you're looking for a relaxing stay. Shelter Island is known for its parks and beaches. Make sure you have time to check out the museums while you're in the area.

How many holiday rentals are there in Shelter Island?

Choose from 86 Expedia holiday rentals in Shelter Island for a memorable holiday.

What can I see and do in Shelter Island?

Sunset Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Gardiner's Bay Country Club and Shelter Island Historical Society are other places to visit while you're in town.

What are holiday rentals like in Shelter Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shelter Island. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a small group gathering.