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Shelter Island Holiday Rentals

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Check prices for these dates

Tonight
9 Jun - 10 Jun
Tomorrow
10 Jun - 11 Jun
This weekend
13 Jun - 15 Jun
Next weekend
20 Jun - 22 Jun

Holiday Rentals in Shelter Island

Montauk Manor
Front of property – evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1191)
"Nice historical building. Rooms well appointed and a beautiful view."
The price is S$422
includes taxes & fees
10 Jun - 11 Jun
Montauk Manor
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (284)
"Great cozy place"
The price is S$274
includes taxes & fees
10 Jun - 11 Jun
Windward Shores Ocean Resort
Montauk Oceanside Suites
Private kitchen

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (379)
"great place to stay"
The price is S$273
includes taxes & fees
10 Jun - 11 Jun
Montauk Oceanside Suites
Offshore Montauk
1 bedroom, laptop workspace, blackout curtains, free WiFi

Offshore Montauk

4.0 star property
The price is S$564
includes taxes & fees
23 Jun - 24 Jun
Offshore Montauk
Driftwood Resort
Private kitchen

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (222)
"The staff was very friendly I will definitely be back again 👍"
The price is S$425
includes taxes & fees
10 Jun - 11 Jun
Driftwood Resort
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (254)
"Quiet, relaxing place to stay, great access to the beach and town!"
The price is S$382
includes taxes & fees
11 Jun - 12 Jun
The Surf Club
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (219)
"After some lengthy travel to get to LI this was an excellent choice to start our vacation. Great accommodations, comfortable and great location. "
The price is S$369
includes taxes & fees
10 Jun - 11 Jun
Cliffside Resort Condominiums
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
The price is S$2,679
includes taxes & fees
17 Jun - 18 Jun
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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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 88 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.