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Shelter Island Holiday Rentals

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Check prices for these dates

Tonight
5 Nov - 6 Nov
Tomorrow
6 Nov - 7 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

Holiday Rentals in Shelter Island

Front of property – evening/night
Montauk Manor
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1260)
"Idillic property, very relaxing, with a wonderful view. We stayed only one night so we did not try the restaurant or the pool but we enjoyed the stay. "
United States
Lydia
The price is S$233
includes taxes & fees
1 Dec - 2 Dec
Montauk Manor
Private kitchen
Montauk Oceanside Suites
Montauk Oceanside Suites
3.0 star property
8.6 out of 10, Excellent, (416)
"We loved it, suite size was great! "
United States
Patrick
The price is S$217
includes taxes & fees
19 Nov - 20 Nov
Montauk Oceanside Suites
Beach nearby
Cliffside Resort Condominiums
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (247)
"Great stay - beautiful place"
United States
Rebecca
Cliffside Resort Condominiums
Living area
Windward Shores Ocean Resort
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (303)
"Easy checking in and out Easy access few steps to beach from first floor unit "
United States
comenius
Windward Shores Ocean Resort
Private kitchen
Driftwood Resort
Driftwood Resort
3.5 star property
9.0 out of 10, Wonderful, (235)
"Great place for families and to enjoy the beauty of Montauk without being in Montauk town. Beautiful beach next to a state park so feels secluded and not crowded. Highly recommend!!!"
United States
Angel
Driftwood Resort
Living area
Offshore Residences
Offshore Residences
4.5 star property
The price is S$863
includes taxes & fees
6 Nov - 7 Nov
Offshore Residences
On the beach, white sand
The Surf Club
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (280)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
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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Top Shelter Island Hotel Reviews

Sea Crest Resort

Sea Crest Resort

10/10 Excellent
"Check in was easy and seamless. The property and rooms are really charming, comfortable and the view is gorgeous! I can’t wait to come back here!"
Catherine 1-night trip
Posted 1 day ago
Sea Crest Resort

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.