Photo by Brian V. Rowe

Search Holiday Rentals in Shelter Island

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

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, (1281)
"Very beautiful place, staff are amazing. Thank you"
United States
Frank
The price is ฿4,324
฿5,551 total
includes taxes & fees
14 Jan - 15 Jan
Montauk Manor
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu
Offshore Residences

Condo in Downtown Montauk

Offshore Residences
4.5 star property
The price is ฿14,943
฿20,637 total
includes taxes & fees
12 Jan - 13 Jan
Offshore Residences
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 ฿45,080
฿54,594 total
includes taxes & fees
15 Jan - 16 Jan
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 Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Everything was Great Immaculate hotel very good location sraff was great"
latoya 1-night trip
Posted 2 days ago
The Harbor Front Inn

Find out more about Shelter Island

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:

  • View our selection of featured holiday rentals in Shelter Island
  • Use the map to find apartments and other holiday homes in the Shelter Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Shelter Island while they last

Look no further and take a look at our great range of rental properties in Shelter Island!

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 89 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. Crescent Beach and Shell 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.