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Shelter Island Vacation Rentals

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In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
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Dec 26 - Dec 28
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Jan 23 - Jan 25

Vacation Rentals in Shelter Island

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, (296)
"Very nice & affordable "
Windward Shores Ocean Resort
Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1252)
"Beautiful grounds, excellent staff"
The price is NT$9,021
NT$10,902 total
includes taxes & fees
Oct 24 - Oct 25
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (414)
"We loved it, suite size was great! "
The price is NT$4,133
NT$5,053 total
includes taxes & fees
Oct 20 - Oct 21
Montauk Oceanside Suites
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (241)
"Great view of the water and nice amenities with the beach and pool."
The price is NT$6,800
NT$9,089 total
includes taxes & fees
Nov 2 - Nov 3
Cliffside Resort Condominiums
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (278)
"Very close walk to the beach great for little ones "
The Surf Club
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (235)
"Great place to stay for small family "
The price is NT$4,372
NT$5,985 total
includes taxes & fees
Oct 13 - Oct 14
Driftwood Resort
Offshore Residences
One Bedroom Condo King with Steam Shower | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

Offshore Residences

4.5 star property
The price is NT$16,068
NT$21,828 total
includes taxes & fees
Oct 6 - Oct 7
Offshore 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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Beautiful grounds, well maintained property. Our room was clean and comfortable. Definitely want to come back and extend our stay with family and friends. It’s a beautiful escape on the East Coast "
David 1-night trip
Posted 2 days ago
Water's Edge Resort & Spa

Find out more about Shelter Island

Find out more about Shelter Island

Search for holiday rentals in Shelter Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Shelter Island using one of the methods below:

  • View our selection of featured holiday rentals in Shelter Island
  • Use the map to find apartments and other holiday homes in the Shelter Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Shelter Island while they last

Look no further and take a look at our great range of rental properties in Shelter Island!

Frequently asked questions

Can I find vacation rentals in Shelter Island?

Yes, we have vacation rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you'd like a relaxing place to 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 vacation rentals are there in Shelter Island?

Choose from 85 Expedia vacation rentals in Shelter Island for a memorable vacation.

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 vacation rentals like in Shelter Island?

Vacation rentals are private properties you can reserve for a couple days or more in Shelter Island. Vacation rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.