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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Shelter Island holiday rentals

A modern house with a deck, outdoor seating, and a fire pit.

1. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is ฿10,796
฿12,335 total
includes taxes & fees
8 Nov - 9 Nov
North Fork Resort
A balcony with a view of the ocean, a lawn, and a house in the background.

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is ฿5,755
฿10,288 total
includes taxes & fees
30 Nov - 1 Dec
Cliffside Resort Condominiums
A spacious hallway with high ceilings, arched columns, and chandeliers.

3. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,419 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is ฿4,638
฿5,954 total
includes taxes & fees
7 Dec - 8 Dec
Montauk Manor
Room

4. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (332 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
United States
Banessa
The price is ฿4,427
฿5,972 total
includes taxes & fees
8 Nov - 9 Nov
Windward Shores Ocean Resort
Room

5. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.4 out of 10, Very good, (460 reviews)
"The room was very clean and well taken care of."
United States
Mitchell
The price is ฿4,573
฿5,589 total
includes taxes & fees
8 Nov - 9 Nov
Montauk Oceanside Suites
Living area

6. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (305 reviews)
"Staff are nice"
United States
na
The price is ฿7,345
฿10,512 total
includes taxes & fees
10 Nov - 11 Nov
The Surf Club
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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Find holiday rentals that suit your style

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Top Shelter Island Hotel Reviews

A two-story house with a balcony, outdoor seating area, and a variety of plants.
Zey Hotel

Zey Hotel

Zey Hotel
Greenport

10/10 Excellent

Nice hotel with parking in a great location
United Kingdom
George
Reviewed June 23, 2026
Zey Hotel

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

What can I see and do in Shelter Island?

Mashomack Preserve and Sunset Beach 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 Wades 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.