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Check prices for these dates

Tonight
19 Aug - 20 Aug
Tomorrow
20 Aug - 21 Aug
This weekend
22 Aug - 24 Aug
Next weekend
29 Aug - 31 Aug

Top Holiday Rentals in Shelter Island

Our top choices for Shelter Island holiday rentals

Montauk Manor
Front of property – evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1238)
"I had the best time and highly recommend this hotel!"
The price is ฿9,656
฿11,669 total
includes taxes & fees
1 Sept - 2 Sept
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (405)
"great place to stay"
The price is ฿6,452
฿7,725 total
includes taxes & fees
3 Sept - 4 Sept
Montauk Oceanside Suites
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (272)
"The front desk was great !!"
The price is ฿10,936
฿14,263 total
includes taxes & fees
10 Sept - 11 Sept
The Surf Club
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (236)
"Great location, great views. Walls are a little thin."
The price is ฿10,783
฿13,732 total
includes taxes & fees
11 Sept - 12 Sept
Cliffside Resort Condominiums
Windward Shores Ocean Resort
Ocean View 2BD Corner King and Queen | Living area | TV

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (291)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is ฿5,430
฿6,912 total
includes taxes & fees
14 Sept - 15 Sept
Windward Shores Ocean Resort
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (229)
"Great place to stay for small family "
The price is ฿6,654
฿8,661 total
includes taxes & fees
3 Sept - 4 Sept
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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"The bed and pillows are the best I’ve ever slept on!! Very clean! Had a wonderful dinner at Fresh Salt. Spa was very nice and had great services. "
Cheryl 1-night trip
Posted 23 hours ago
Saybrook Point Resort & Marina

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. Wades Beach and Gardiner's Bay Country Club 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.