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Shelter Island Vacation Rentals

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Check prices for these dates

Tonight
Jun 23 - Jun 24
Tomorrow
Jun 24 - Jun 25
This weekend
Jun 27 - Jun 29
Next weekend
Jul 4 - Jul 6

Vacation Rentals in Shelter Island

Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1200)
"The property was gorgeous, and the staff were very friendly and eager to assist. Also, the restaurant was very good!"
The price is NT$10,764
NT$12,877 total
includes taxes & fees
Jun 24 - Jun 25
Montauk Manor
Offshore Montauk
1 bedroom, laptop workspace, blackout drapes, free WiFi

Offshore Montauk

4.0 star property
4.0 out of 10, (1)
"This is a newly completed/renovated property. Hopefully with time it will develop to a better condition and as it’s advertised, luxury. But right now expect minimal comfort and amenities. It’s like a motel and not a hotel; not worth the price tag. "
The price is NT$11,639
NT$16,671 total
includes taxes & fees
Jun 25 - Jun 26
Offshore Montauk
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (285)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is NT$7,963
NT$9,741 total
includes taxes & fees
Jun 29 - Jun 30
Windward Shores Ocean Resort
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (383)
"great place to stay"
The price is NT$5,526
NT$6,634 total
includes taxes & fees
Jun 25 - Jun 26
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, (224)
"The staff was very friendly I will definitely be back again 👍"
The price is NT$9,155
NT$11,422 total
includes taxes & fees
Jun 24 - Jun 25
Driftwood Resort
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (256)
"Quiet, relaxing place to stay, great access to the beach and town!"
The price is NT$6,944
NT$9,539 total
includes taxes & fees
Jun 25 - Jun 26
The Surf Club
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (222)
"After some lengthy travel to get to LI this was an excellent choice to start our vacation. Great accommodations, comfortable and great location. "
The price is NT$6,611
NT$8,837 total
includes taxes & fees
Jun 24 - Jun 25
Cliffside Resort Condominiums
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
The price is NT$58,916
NT$71,351 total
includes taxes & fees
Jun 26 - Jun 27
Canoe Place Waterfront 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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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 87 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 Shell Beach 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.