Photo by tom owens

Shelter Island Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Shelter Island

Montauk Manor
Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, 1,026 reviews
"Montauk Manor is a beautiful property and very well maintained. The views are spectacular. Monty's restaurant had delicious breakfasts and dinners. The pool was very nice. The accommodations were very clean. The outdoor patio was an added bonus. The staff were very pleasant and helpful."
The price is P 25,727
per night
Jun 16 - Jun 17
Montauk Manor
Windward Shores Ocean Resort
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, 239 reviews
"On the beach with property chairs and umbrellas. Kitchen poorly stocked with utensils etc. "
The price is P 19,948
per night
Jun 16 - Jun 17
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, 223 reviews
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is P 16,775
per night
Jun 24 - Jun 25
The Surf Club
Montauk Oceanside Suites
Private kitchen
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very Good, 303 reviews
"10/10 will be back again"
The price is P 14,299
per night
Jun 18 - Jun 19
Montauk Oceanside Suites
Driftwood Resort
Private kitchen
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, 190 reviews
"Its on the beach which is great "
The price is P 13,060
per night
Jun 20 - Jun 21
Driftwood Resort
Cliffside Resort Condominiums
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, 184 reviews
"quiet"
The price is P 16,477
per night
Jun 27 - Jun 28
Cliffside Resort Condominiums
Don't see what you're looking for?
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

Gurney's Montauk Resort & Seawater Spa
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very Good, 572 reviews
"Great time beautiful property"
The price is P 45,096
per night
Jun 14 - Jun 15
Gurney's Montauk Resort & Seawater Spa
The Bentley Hotel Southampton
Terrace/patio
The Bentley Hotel Southampton
2.0 star property
9.4 out of 10, Exceptional, 82 reviews
"."
The price is P 14,979
per night
Jun 20 - Jun 21
The Bentley Hotel Southampton
Pier Blue Inn Old Saybrook - Essex
Property grounds
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.8 out of 10, Good, 795 reviews
"Cute and reasonable priced rooms. Planned on one night and ended up staying for two nights. "
The price is P 4,630
per night
Jun 19 - Jun 20
Pier Blue Inn Old Saybrook - Essex
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
  • 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 89 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. Shell Beach 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.

Recent reviews of Shelter Island properties
Expedia verified reviews

The Montauk Soundview

The Montauk Soundview

5/5 Excellent
"Nice location and staff are very helpful. "
A verified traveler stayed at The Montauk Soundview
Posted 1 day ago
The Montauk Soundview