Villas in Shelter Island

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 29 Villas in Shelter Island with updated reviews, rates, and availability.

Other property types in Shelter Island

Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1021)
"Best affordable hotel in Montauk"
The price is $168
$211 total
includes taxes & fees
May 23 - May 24
Montauk Manor
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very Good, (296)
"We enjoyed our stay!"
The price is $156
$188 total
includes taxes & fees
May 23 - May 24
Montauk Oceanside Suites
On the beach, white sand
The Surf Club
3.5 star property
8.4 out of 10, Very Good, (220)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is $161
$238 total
includes taxes & fees
May 28 - May 29
The Surf Club
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.

Shelter Island Villas information

Number of reviews
15
Accommodation
29 Villas
Lowest Price
Highest Price

Frequently asked questions

Why book your villa in Shelter Island with Expedia?
Booking a villa in Shelter Island is as simple as deciding on your travel dates and picking the option that checks your boxes. On the lookout for something budget friendly or upmarket, or a stay that also includes a pool? Use Expedia’s search filters to narrow your results and find your ideal match.
How can I find cheap villas in Shelter Island?
A fantastic way to compare cheap villas in Shelter Island is with Expedia’s handy filter tool. Refine your search by budget, star rating and amenities to access awesome deals in just a few keystrokes.

Recent reviews of Shelter Island hotels
Expedia verified reviews

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

5/5 Excellent
"Great location !! Room was spacious and very comfortable and clean !!!"
A verified traveler stayed at Beachcomber Resort at Montauk
Posted 1 day ago
Beachcomber Resort at Montauk