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Search Holiday Rentals in Shelter Island

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Check prices for these dates

Tonight
16 Apr - 17 Apr
Tomorrow
17 Apr - 18 Apr
This weekend
18 Apr - 20 Apr
Next weekend
25 Apr - 27 Apr

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, (1155)
"The manor is great!"
The price is ฿4,984
฿6,352 total
includes taxes & fees
5 May - 6 May
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (369)
"We stayed for a night and it was great. It was great location and setting. Overall stay was fantastic. Bathtub was a bit old, could not hold the water and if you are more than 1 person, you have to space your baths so you can all enjoy warm water. "
The price is ฿4,567
฿5,583 total
includes taxes & fees
24 Apr - 25 Apr
Montauk Oceanside Suites
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (282)
"Condo was great, family of 5 , clean, no hassle"
The price is ฿4,791
฿6,204 total
includes taxes & fees
22 Apr - 23 Apr
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, (251)
"The pictures of the property showed the bed in the bedroom facing the window with direct ocean views I was dis appointed to find out the bed was moved and no longer faced the ocean view."
The price is ฿6,796
฿9,590 total
includes taxes & fees
14 May - 15 May
The Surf Club
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
The price is ฿4,833
฿6,980 total
includes taxes & fees
30 Apr - 1 May
Cliffside Resort Condominiums
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (214)
"We were visiting our so. And just needed an inexpensive..relatively..place to stay….. this was quite convenient…. We had a good night sleep…took a walk to beach..had a great chat with one of the ‘beach boys’ and thought it was lovely……"
The price is ฿4,973
฿6,412 total
includes taxes & fees
14 May - 15 May
Driftwood Resort
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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Other types of properties in Shelter Island you may be interested in

Montauk Manor
Front of property – evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1155)
"The manor is great!"
The price is ฿4,984
฿6,352 total
includes taxes & fees
5 May - 6 May
Montauk Manor
Pier Blue Inn Old Saybrook - Essex
Property grounds

Pier Blue Inn Old Saybrook - Essex

2.0 star property
7.8 out of 10, Good, (945)
"the property was close to the ocean. very pet friendly and accommodated our needs well"
The price is ฿2,651
฿3,049 total
includes taxes & fees
19 Apr - 20 Apr
Pier Blue Inn Old Saybrook - Essex
Montauk Yacht Club
Indoor pool, 2 outdoor pools

Montauk Yacht Club

4.0 star property
8.6 out of 10, Excellent, (1000)
"When we checked out there was a "kid" at the pool who was I suppose looking after the area. It was raining and I was going to put my bags by the door. Before I knew it David came running up and asked if he could help me. This is a lesson in customer service. It's people like David and your other employees that make this such a great place to stay. Thank you David for caring."
The price is ฿7,249
฿8,282 total
includes taxes & fees
29 Apr - 30 Apr
Montauk Yacht 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.

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

What can I see and do in Shelter Island?

Sunset Beach and Wades 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 Crescent 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.