Photo by Brian V. Rowe

Shelter Island Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Shelter Island holiday rentals

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Montauk Manor

Aparthotel in Montauk

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1271)
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is S$229
includes taxes & fees
6 Jan - 7 Jan, 2026
Montauk Manor
Private kitchen
Canoe Place Waterfront Residences

Condo in Hampton Bays

Canoe Place Waterfront Residences
4.0 star property
10.0 out of 10, Exceptional, (1)
The price is S$2,957
includes taxes & fees
28 Dec - 29 Dec
Canoe Place Waterfront Residences
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

The Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"Great stay, will definitely go again"
ANTONIO J 2-night trip
Posted 3 days ago
The Shoals Suites and Slips

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 88 Expedia holiday rentals in Shelter Island for a memorable holiday.

What can I see and do in Shelter Island?

Sunset Beach and Mashomack Preserve are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Shelter Island Historical Society and Crescent Beach 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.