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Shelter Island Holiday Rentals

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Check prices for these dates

Tonight
1 Jul - 2 Jul
Tomorrow
2 Jul - 3 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Holiday Rentals in Shelter Island

American Beech in Greenport - Petite King Room 7
Terrace/patio

American Beech in Greenport - Petite King Room 7

8.8 out of 10, Excellent, (3)
"We thoroughly enjoyed our stay!"
American Beech in Greenport - Petite King Room 7
American Beech in Greenport NY - King Suite 1
1 bedroom, iron/ironing board, Internet

American Beech in Greenport NY - King Suite 1

10.0 out of 10, Exceptional, (5)
"Perfect Great place"
American Beech in Greenport NY - King Suite 1
American Beech - Deluxe King Suite 14
Outdoor dining

American Beech - Deluxe King Suite 14

10.0 out of 10, Exceptional, (2)
American Beech - Deluxe King Suite 14
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 86 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. Mashomack Preserve and Shell 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.