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Shelter Island Holiday Rentals

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Check prices for these dates

Tonight
21 Jul - 22 Jul
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22 Jul - 23 Jul
This weekend
25 Jul - 27 Jul
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1 Aug - 3 Aug

Holiday Rentals in Shelter Island

Montauk Manor
Front of property – evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1216)
"Beautiful property and spacious rooms "
The price is S$706
includes taxes & fees
22 Jul - 23 Jul
Montauk Manor
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (262)
"Quiet, relaxing place to stay, great access to the beach and town!"
The price is S$564
includes taxes & fees
22 Jul - 23 Jul
The Surf Club
Montauk Oceanside Suites
Private kitchen

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (393)
"great place to stay"
The price is S$422
includes taxes & fees
23 Jul - 24 Jul
Montauk Oceanside Suites
Windward Shores Ocean Resort
Living area

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (289)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is S$657
includes taxes & fees
27 Jul - 28 Jul
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (228)
"Very nice, clean and cosy place! Highly recommend!"
The price is S$550
includes taxes & fees
22 Jul - 23 Jul
Cliffside Resort Condominiums
Driftwood Resort
Private kitchen

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (225)
"Phenomenal property and our room had a private sand patio. Service was extremely attentive and friendly. The beach was very spacious and pretty clean."
The price is S$717
includes taxes & fees
28 Jul - 29 Jul
Driftwood Resort
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
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 Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"We could not recommend this property more! The rooms are fabulous and the grounds are beautiful. We had a room on the ground and our dog loved the easy access outside. The rooms are decorated beautifully as well - very chic and spacious! Cant wait to come back here in the Fall."
Samantha 1-night trip
Posted 2 days ago
The Bentley Hotel Southampton

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?

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. 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.