Shelter Island Holiday Rentals

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Holiday Rentals in Shelter Island

Front of property – evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1021)
"Best affordable hotel in Montauk"
The price is S$285
includes taxes & fees
28 May - 29 May
Montauk Manor
Private kitchen
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (296)
"We enjoyed our stay!"
The price is S$266
includes taxes & fees
6 Jun - 7 Jun
Montauk Oceanside Suites
On the beach, white sand
The Surf Club
3.5 star property
8.4 out of 10, Very good, (220)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is S$340
includes taxes & fees
29 May - 30 May
The Surf Club
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View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (236)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is S$350
includes taxes & fees
29 May - 30 May
Windward Shores Ocean Resort
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (181)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is S$346
includes taxes & fees
27 May - 28 May
Cliffside Resort Condominiums
Private kitchen
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (185)
"Every room in the hotel has a little garden in the backyard which is linked with the park, it’s super natural and quiet and definitely worth to stay"
The price is S$303
includes taxes & fees
9 Jun - 10 Jun
Driftwood Resort
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See all available properties in Shelter Island
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.

Other types of properties in Shelter Island you may be interested in

Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very good, (569)
"Great time beautiful property"
The price is S$969
includes taxes & fees
29 May - 30 May
Gurney's Montauk Resort & Seawater Spa
Property grounds
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.6 out of 10, Good, (780)
"This is a no-frills hotel. However we had a mini fridge, microwave and coffee maker in our room. VERY spacious. Staff were friendly and at the front desk when we needed them to be there. A lady came to our door once to see if we needed fresh towels (we were there for 6 days). We will stay here on a return visit. Thanks Pier Blue staff"
The price is S$138
includes taxes & fees
26 May - 27 May
Pier Blue Inn Old Saybrook - Essex
Front of property – evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1021)
"Best affordable hotel in Montauk"
The price is S$285
includes taxes & fees
28 May - 29 May
Montauk Manor
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. Shell 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.

Recent reviews of Shelter Island properties
Expedia verified reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

5/5 Excellent
"Great time beautiful property"
A verified traveller stayed at Gurney's Montauk Resort & Seawater Spa
Posted 2 days ago
Gurney's Montauk Resort & Seawater Spa