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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sep - 20 Sep

Our top choices for Shelter Island holiday rentals

Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (19 reviews)
"Great stay & great staff!"
United States
James
The price is 6.757.492 ₫
7.720.434 ₫ total
includes taxes & fees
28 May - 29 May
North Fork Resort
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,353 reviews)
"Had a wonderful stay"
United States
Meghan
The price is 6.304.355 ₫
7.719.145 ₫ total
includes taxes & fees
4 Jun - 5 Jun
Montauk Manor
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.
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Top Shelter Island Hotel Reviews

Montauk Blue Hotel

Montauk Blue Hotel

10/10 Excellent
"The view of the ocean was beautiful and the room was clean. The front desk people were very professional and helpful. I highly recommend staying here."
Frederick 2-night trip
Posted 6 hours ago
Montauk Blue Hotel

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 90 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 Mashomack Preserve 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.