Shelter Island Vacation Rentals

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Vacation Rentals in Shelter Island

Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1020)
"Best affordable hotel in Montauk"
The price is NT$5,391
NT$6,780 total
includes taxes & fees
May 22 - May 23
Montauk Manor
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 NT$7,894
NT$10,404 total
includes taxes & fees
May 19 - May 20
Cliffside Resort Condominiums
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 NT$4,933
NT$6,327 total
includes taxes & fees
May 19 - May 20
Windward Shores Ocean Resort
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Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (184)
"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 NT$5,214
NT$6,648 total
includes taxes & fees
Jun 2 - Jun 3
Driftwood Resort
On the beach, white sand
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (219)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is NT$7,206
NT$9,972 total
includes taxes & fees
Jun 9 - Jun 10
The Surf Club
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very Good, (295)
"We enjoyed our stay!"
The price is NT$5,011
NT$6,040 total
includes taxes & fees
May 22 - May 23
Montauk Oceanside Suites
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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

Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1020)
"Best affordable hotel in Montauk"
The price is NT$5,391
NT$6,780 total
includes taxes & fees
May 22 - May 23
Montauk Manor
Indoor pool, outdoor pool
Hyatt Place Long Island East End
3.0 star property
9.0 out of 10, Wonderful, (1001)
"Very nice "
The price is NT$4,606
NT$5,257 total
includes taxes & fees
May 23 - May 24
Hyatt Place Long Island East End
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very Good, (565)
"Amazing beds "
The price is NT$16,947
NT$23,104 total
includes taxes & fees
May 29 - May 30
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.

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
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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 86 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. Gardiner's Bay Country Club and Shelter Island Historical Society 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.

Recent reviews of Shelter Island properties
Expedia verified reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

5/5 Excellent
Nice hotel
"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"
A verified traveler stayed at Pier Blue Inn Old Saybrook - Essex
Posted 14 hours ago
Pier Blue Inn Old Saybrook - Essex