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Search Holiday Rentals in Shelter Island

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Top Holiday Rentals in Shelter Island

Montauk Manor
Front of property – evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1052)
"Great hotel loved the architecture and the grounds. "
The price is 6.617.976 ₫
8.033.549 ₫ total
includes taxes & fees
30 Sept - 1 Oct
Montauk Manor
Windward Shores Ocean Resort
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (252)
"Very nice place to spend a weekend with friends."
The price is 3.240.374 ₫
4.232.456 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Windward Shores Ocean Resort
The Surf Club
On the beach, white sand
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (247)
"On the beach Heated pool Great facilities"
The price is 6.197.436 ₫
8.408.839 ₫ total
includes taxes & fees
10 Oct - 11 Oct
The Surf Club
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (334)
"The hotels in this area have been around for a very long time. They have that weathered look. This hotel had what we were looking for. No frills and clean. We had a one bedroom, with an open dining /living room and galley kitchen. The kitchen came equipped with coffee maker, dishwasher, full size refrigerator and stove. The location was great one block from the ocean, one block to the center of town. Take the LIRR taxi over and you don’t need a car for a weekend getway. Enjoy! "
The price is 3.456.300 ₫
4.190.401 ₫ total
includes taxes & fees
23 Oct - 24 Oct
Montauk Oceanside Suites
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils
Driftwood Resort
3.5 star property
9.0 out of 10, Wonderful, (202)
"Great location. Beautiful beach. Perfect for a 2 - 3 night getaway."
The price is 4.256.065 ₫
5.391.770 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Driftwood Resort
Cliffside Resort Condominiums
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (202)
"Beautiful condo Convienent Spacious Only issue check in 4 pm Checkout at 10 am "
The price is 7.670.065 ₫
9.821.953 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Cliffside Resort Condominiums
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Other types of properties in Shelter Island you may be interested in

Pier Blue Inn Old Saybrook - Essex
Property grounds
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.6 out of 10, Good, (857)
"Very helpful, real people! Many dinning options within two minutes. "
The price is 1.942.847 ₫
2.234.274 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Pier Blue Inn Old Saybrook - Essex
Montauk Yacht Club
2 outdoor pools
Montauk Yacht Club
4.0 star property
8.4 out of 10, Very good, (1002)
"beautiful room and view , stayed with my 2 year old staff was lovely "
The price is 5.877.727 ₫
8.111.233 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Montauk Yacht Club
Gurney's Montauk Resort & Seawater Spa
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very good, (594)
"Beautiful "
The price is 14.632.835 ₫
19.949.443 ₫ total
includes taxes & fees
8 Oct - 9 Oct
Gurney's Montauk Resort & Seawater Spa
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.

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 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.