Shelter Island Vacation Rentals

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Vacation Rentals in Shelter Island

Front of property – evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1016)
"The hotel was beautiful. Town is very close by and they offer a shuttle service to take you around. It's nice overall."
The price is RM796
RM1,001 total
includes taxes & fees
22 May - 23 May
Montauk Manor
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (180)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is RM1,166
RM1,537 total
includes taxes & fees
14 May - 15 May
Cliffside Resort Condominiums
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (233)
"Everything was just as described!"
The price is RM729
RM934 total
includes taxes & fees
19 May - 20 May
Windward Shores Ocean Resort
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Private kitchen
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (182)
"Every room in the hotel has a little garden in the backyard which is linked with the park, it’s super natural and quiet and definitely worth to stay"
The price is RM770
RM982 total
includes taxes & fees
2 Jun - 3 Jun
Driftwood Resort
On the beach, white sand
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (219)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is RM1,002
RM1,401 total
includes taxes & fees
12 May - 13 May
The Surf Club
Private kitchen
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (295)
"Only wish it was more affordable in the summer to take my family. Besides that, clean, confortable, very pleasant."
The price is RM740
RM892 total
includes taxes & fees
22 May - 23 May
Montauk Oceanside Suites
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See all available properties in Shelter Island
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.

Other types of properties in Shelter Island you may be interested in

Front of property – evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1016)
"The hotel was beautiful. Town is very close by and they offer a shuttle service to take you around. It's nice overall."
The price is RM796
RM1,001 total
includes taxes & fees
22 May - 23 May
Montauk Manor
Indoor pool, outdoor pool
Hyatt Place Long Island East End
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Its a family trip to celebrate my wife's birthday. We love the hotel and the surroundings. The staff is so friendly, and service is superb! They even give us nice gifts like wine and chocolate.... Thanks so much, we definitely will return."
The price is RM721
RM823 total
includes taxes & fees
19 May - 20 May
Hyatt Place Long Island East End
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very good, (561)
"front desk staff irritating as can be "
The price is RM2,112
RM2,880 total
includes taxes & fees
12 May - 13 May
Gurney's Montauk Resort & Seawater Spa
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.

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
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  • 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 86 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 Shelter Island Historical Society 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.

Recent reviews of Shelter Island properties
Expedia verified reviews

The Sunset Montauk

The Sunset Montauk

5/5 Excellent
"This play was exceptionally clean, especially for a beach hotel. Also the grounds were well kept and child friendly and the room rate was affordable. Would definitely stay there again!"
A verified traveller stayed at The Sunset Montauk
Posted 1 day ago
The Sunset Montauk