Search Holiday Rentals in Shelter Island

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20 Nov - 21 Nov
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21 Nov - 22 Nov
This weekend
21 Nov - 23 Nov
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28 Nov - 30 Nov

Top Holiday Rentals in Shelter Island

Front of property – evening/night
Montauk Manor

Aparthotel in Montauk

3.5 star property
9.2 out of 10, Wonderful, (1262)
"Always excellent, even suring my eleventh stay."
United States
Daryl
The price is 3.655.852 ₫
4.692.996 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Montauk Manor
Free WiFi, bed sheets
North Fork Cottages & RV Resort

Cottage in Greenport

3.0 star property
9.4 out of 10, Exceptional, (6)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is 5.143.515 ₫
5.876.466 ₫ total
includes taxes & fees
23 Nov - 24 Nov
North Fork Cottages & RV Resort
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu
Offshore Residences

Condo in Downtown Montauk

4.5 star property
The price is 12.634.583 ₫
17.448.582 ₫ total
includes taxes & fees
25 Nov - 26 Nov
Offshore 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

Sound View Greenport

Sound View Greenport

10/10 Excellent
"The room was very clean, bed was comfy, and the sounds of the water outside were lovely. I did arrive very late and all parking spots were taken which was sort of inconvenient as it is a bit of a walk to park by other rooms. Check in process was super smooth."
Hillary 1-night trip
Posted 3 days ago
Sound View Greenport

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 84 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 Mashomack Preserve 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.