Photo by tom owens

Search Holiday Rentals in Shelter Island

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

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

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, (1200)
"The property was gorgeous, and the staff were very friendly and eager to assist. Also, the restaurant was very good!"
The price is 9.524.750 ₫
11.393.900 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Montauk Manor
Offshore Montauk
1 bedroom, laptop workspace, blackout curtains, free WiFi

Offshore Montauk

4.0 star property
8.0 out of 10, Very good, (3)
"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 10.298.227 ₫
14.751.191 ₫ total
includes taxes & fees
25 Jun - 26 Jun
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 7.046.224 ₫
8.619.049 ₫ total
includes taxes & fees
29 Jun - 30 Jun
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 4.889.371 ₫
5.870.328 ₫ total
includes taxes & fees
25 Jun - 26 Jun
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 5.299.772 ₫
6.908.407 ₫ total
includes taxes & fees
25 Jun - 26 Jun
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 22.929.953 ₫
27.618.377 ₫ total
includes taxes & fees
23 Jul - 24 Jul
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 14.334.944 ₫
17.512.996 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Cliffside Resort Condominiums
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
The price is 52.131.345 ₫
63.133.803 ₫ total
includes taxes & fees
7 Jul - 8 Jul
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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. Mashomack Preserve and Shell 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.