Shelter Island Vacation Rentals

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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Shelter Island holiday rentals

Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (15 reviews)
"Great stay & great staff!"
United States
James
The price is RM1,175
RM1,342 total
includes taxes & fees
1 Jun - 2 Jun
North Fork Resort
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,346 reviews)
"Had a wonderful stay"
United States
Meghan
The price is RM641
RM809 total
includes taxes & fees
25 May - 26 May
Montauk Manor
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (312 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is RM782
RM1,001 total
includes taxes & fees
26 May - 27 May
Windward Shores Ocean Resort
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is RM796
RM1,082 total
includes taxes & fees
31 May - 1 Jun
Cliffside Resort Condominiums
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

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"The room was extremely clean and staff was very helpful in keeping our 4 rooms together."
Michele 2-night trip
Posted 4 hours ago
Beachcomber Resort at Montauk

Find out more about Shelter Island

Search for holiday rentals in Shelter Island on Expedia.co.uk! 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 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.