Shelter Island Vacation Rentals

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Vacation Rentals in Shelter Island

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1016)
"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 NT$5,447
per night
May 15 - May 16
Montauk Manor
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 NT$7,976
per night
May 13 - May 14
Cliffside Resort Condominiums
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (233)
"Everything was just as described!"
The price is NT$4,984
per night
May 13 - May 14
Windward Shores Ocean Resort
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Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (183)
"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 NT$5,268
per night
Jun 2 - Jun 3
Driftwood Resort
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (219)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is NT$7,258
per night
May 28 - May 29
The Surf Club
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very Good, (295)
"We enjoyed our stay!"
The price is NT$5,063
per night
May 23 - May 24
Montauk Oceanside Suites
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See all available properties in Shelter Island
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

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1016)
"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 NT$5,447
per night
May 15 - May 16
Montauk Manor
Hyatt Place Long Island East End
3.0 star property
9.0 out of 10, Wonderful, (1002)
"."
The price is NT$4,931
per night
May 19 - May 20
Hyatt Place Long Island East End
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very Good, (562)
"front desk staff irritating as can be "
The price is NT$17,070
per night
May 23 - May 24
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.

Search for holiday rentals in Shelter Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Shelter Island using one of the methods below:

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Frequently asked questions

Can I find vacation rentals in Shelter Island?

Yes, we have vacation rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you'd like a relaxing place to 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 vacation rentals are there in Shelter Island?

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

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 vacation rentals like in Shelter Island?

Vacation rentals are private properties you can reserve for a couple days or more in Shelter Island. Vacation rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.

Recent reviews of Shelter Island properties
Expedia verified reviews