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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Shelter Island holiday rentals

Terrace/patio

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
The price is 4.372.885 ₫
7.866.381 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (63 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is 6.892.301 ₫
7.874.454 ₫ total
includes taxes & fees
13 Oct - 14 Oct
North Fork Resort
A spacious hallway with high ceilings, arched columns, and chandeliers.

3. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,414 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is 3.911.846 ₫
4.976.220 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Montauk Manor
Room

4. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (324 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is 3.692.969 ₫
4.922.665 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Windward Shores Ocean Resort
Room

5. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (255 reviews)
"Great right on the beach property with nice pool."
United States
Julian
The price is 3.060.990 ₫
4.341.871 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Driftwood Resort
Room

6. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (456 reviews)
"The room was very clean and spacious."
United States
Jadana
The price is 3.667.356 ₫
4.471.457 ₫ total
includes taxes & fees
21 Oct - 22 Oct
Montauk Oceanside Suites
Living area

7. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (303 reviews)
"Staff are nice"
United States
na
The price is 5.485.041 ₫
7.896.125 ₫ total
includes taxes & fees
26 Oct - 27 Oct
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

Montauk Blue Hotel

Montauk Blue Hotel

10/10 Excellent
"All good. Beautiful relaxing time on the beach and near town. Weather fantastic! Come back every year."
Jeanne 2-night trip
Posted 10 hours ago
Montauk Blue Hotel

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 87 Expedia holiday rentals in Shelter Island for a memorable holiday.

What can I see and do in Shelter Island?

Mashomack Preserve and Sunset 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 Wades 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.