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Shelter Island Holiday Rentals

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Check prices for these dates

Tonight
27 Jul - 28 Jul
Tomorrow
28 Jul - 29 Jul
Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 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, (1220)
"Great hotel"
The price is S$704
includes taxes & fees
28 Jul - 29 Jul
Montauk Manor
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (264)
"Quiet, relaxing place to stay, great access to the beach and town!"
The price is S$892
includes taxes & fees
3 Aug - 4 Aug
The Surf Club
Montauk Oceanside Suites
Private kitchen

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (397)
"Loved it, amazing area & spacious room. "
The price is S$520
includes taxes & fees
29 Jul - 30 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$607
includes taxes & fees
28 Jul - 29 Jul
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (229)
"Great property overall with beautiful grounds, a pool and access to the beach. Condos are spacious and equipped with bathroom and kitchen items. Ours had a patio with a great view of the water! We will definitely stay here again. "
The price is S$548
includes taxes & fees
29 Jul - 30 Jul
Cliffside Resort Condominiums
Driftwood Resort
Private kitchen

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (226)
"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$798
includes taxes & fees
28 Jul - 29 Jul
Driftwood Resort
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
10.0 out of 10, Exceptional, (1)
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

Montauk Manor

Montauk Manor

10/10 Excellent
"We go to Montauk Manor every year as a family. It’s clean quiet and if you need to get anywhere, they provide a shuttle."
Scott 3-night trip
Posted 2 days ago
Montauk Manor

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 85 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.