Villas in Shelter Island

Most properties are fully refundable. Because flexibility matters.

Save 10% or more on over 100,000 hotels worldwide as a One Key member.

Search over 2.9 million properties and 550 airlines worldwide.

Compare 27 Villas in Shelter Island with updated reviews, rates, and availability.

1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Pool | Outdoor pool, a heated pool
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
Interior
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
10.0 out of 10, Exceptional, (13)
"Rented this place out for my partner’s 25th birthday. Tony was amazing, went out of his way to allow us to come early to check it out and get the floor plan - very communicative, the place was absolutely gorgeous. The weekend went off without a hitch and I gotta hand it to Tony for making it all happen."
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
Villa Direen - Modern East Hampton Villa
Luxury Villa (6 Bedrooms) | Living area | TV
Villa Direen - Modern East Hampton Villa
4.0 star property
Villa Direen - Modern East Hampton Villa
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
New Construction Greenport Pool House - 3 Blocks from Town
Property grounds
New Construction Greenport Pool House - 3 Blocks from Town
New Construction Greenport Pool House - 3 Blocks from Town
Waterfront Villa with Private Beach in Montauk
4 bedrooms, desk, iron/ironing board, cribs/infant beds
Waterfront Villa with Private Beach in Montauk
Waterfront Villa with Private Beach in Montauk
Live on the Water: Dock, Beach, Boat, Kayak & Fish
Property grounds
Live on the Water: Dock, Beach, Boat, Kayak & Fish
10.0 out of 10, Exceptional, (1)
"I have rented many houses in the Hamptons and this was the best by far! Family friendly, great hosts and magical spot!"
Live on the Water: Dock, Beach, Boat, Kayak & Fish
Beautiful Mediterranean villa
Pool
Beautiful Mediterranean villa
10.0 out of 10, Exceptional, (1)
"The home was clean pool was great And the owners wonderful"
Beautiful Mediterranean villa
MODERN 5 BEDROOM MONTAUK BEACH HOME
Fridge, microwave, oven, stovetop
MODERN 5 BEDROOM MONTAUK BEACH HOME
MODERN 5 BEDROOM MONTAUK BEACH HOME
Villa Roman
Exterior
Villa Roman
3.5 star property
Villa Roman
Villa Machis
Outdoor pool
Villa Machis
3.5 star property
Villa Machis
Hilltop Villa overlooking the Harbor with gorgeous sunsets
Pool
Hilltop Villa overlooking the Harbor with gorgeous sunsets
Hilltop Villa overlooking the Harbor with gorgeous sunsets
Villa Lavender
Living area
Villa Lavender
3.5 star property
Villa Lavender
Chic Modern Retreat In Wainscott
View from property
Chic Modern Retreat In Wainscott
Chic Modern Retreat In Wainscott
Villa Nostro Palazzo
Front of property
Villa Nostro Palazzo
4.0 star property
Villa Nostro Palazzo
Villa Vajra
Outdoor pool
Villa Vajra
3.5 star property
Villa Vajra
Villa Isaiah
Outdoor pool
Villa Isaiah
3.5 star property
Villa Isaiah
Villa Spectrum
Front of property
Villa Spectrum
3.5 star property
Villa Spectrum
Villa Sofia
Outdoor pool, a heated pool
Villa Sofia
3.5 star property
Villa Sofia
Villa Skylar
Exterior
Villa Skylar
3.5 star property
Villa Skylar
Villa Red Hut
Outdoor pool
Villa Red Hut
3.5 star property
Villa Red Hut
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 property types in Shelter Island

Montauk Manor
Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1019)
"Best affordable hotel in Montauk"
The price is $168
$211 total
includes taxes & fees
20 May - 21 May
Montauk Manor
Montauk Oceanside Suites
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 $156
$188 total
includes taxes & fees
22 May - 23 May
Montauk Oceanside Suites
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
27 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 亿客行 verified reviews

The Atlantic Hotel

The Atlantic Hotel

5/5 Excellent
Non Hampton prices.
"Great prices, huge room, convenient and super friendly staff. Have stayed the past 3 weeks for business, good location"
A verified traveler stayed at The Atlantic Hotel
Posted 19 hours ago
The Atlantic Hotel