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Search Villas in Shelter Island

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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Villas in Shelter Island

Hampton Private Retreat - last minute offer June 23-
Exterior

Hampton Private Retreat - last minute offer June 23-

10.0 out of 10, Exceptional, (19)
"We enjoyed Connieā€™s beautiful home. The kitchen was fully stocked, the bedrooms were very comfortable and the location was perfect. My family would definitely stay here again!"
Hampton Private Retreat - last minute offer June 23-
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Outdoor pool, a heated pool

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

10.0 out of 10, Exceptional, (1)
"Very nice house In great shape and outstanding pool area."
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
New Construction Greenport Pool House - 3 Blocks from Town
Outdoor pool, a heated pool

New Construction Greenport Pool House - 3 Blocks from Town

The price is SARĀ 3,057
SARĀ 5,213 total
includes taxes & fees
25 Jun - 26 Jun
New Construction Greenport Pool House - 3 Blocks from Town
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, (17)
"House was amazing and owner was fantastic! Highly recommend!!!"
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
Villa Direen Modern East Hampton Villa
Front of property

Villa Direen Modern East Hampton Villa

3.5 star property
Villa Direen Modern East Hampton Villa
Villa Flasses
Outdoor pool

Villa Flasses

3.0 star property
Villa Flasses
Villa Isaiah
Luxury Villa (6 Bedrooms) | Private kitchen | Full-size fridge, microwave, oven, stovetop

Villa Isaiah

3.5 star property
Villa Isaiah
Villa Verde - Sanctuary @ Bridge
Terrace/patio

Villa Verde - Sanctuary @ Bridge

Villa Verde - Sanctuary @ Bridge
TBD by Rove Travel 7BR Pool Hot Tub
Villa | Internet

TBD by Rove Travel 7BR Pool Hot Tub

2.0 star property
TBD by Rove Travel 7BR Pool Hot Tub
Villa Skylar
40-inch flat-screen TV with cable channels, Smart TV, fireplace

Villa Skylar

3.5 star property
Villa Skylar
Luxurious beach house on the Long Island sound
Living area

Luxurious beach house on the Long Island sound

Luxurious beach house on the Long Island sound
Villa Vajra
Exterior

Villa Vajra

3.5 star property
Villa Vajra
Villa Red Hut
Outdoor pool

Villa Red Hut

3.5 star property
Villa Red Hut
Waterfront Villa with Private Beach in Montauk
4 bedrooms, desk, iron/ironing board, free WiFi

Waterfront Villa with Private Beach in Montauk

Waterfront Villa with Private Beach in Montauk
MODERN 5 BEDROOM MONTAUK BEACH HOME
Interior

MODERN 5 BEDROOM MONTAUK BEACH HOME

MODERN 5 BEDROOM MONTAUK BEACH HOME
YOU CAN WATCH THE SUNRISE FROM YOUR BALCONY
Outdoor pool, a heated pool

YOU CAN WATCH THE SUNRISE FROM YOUR BALCONY

YOU CAN WATCH THE SUNRISE FROM YOUR BALCONY
Villa Baloch
Balcony

Villa Baloch

3.0 star property
Villa Baloch
Chic Modern Retreat In Wainscott
Terrace/patio

Chic Modern Retreat In Wainscott

Chic Modern Retreat In Wainscott
East Hampton Villa
House, Multiple Beds (East Hampton Villa) | Balcony

East Hampton Villa

3.5 star property
East Hampton Villa
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
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

Why book your villa in Shelter Island with Expedia?
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How can I find cheap villas in Shelter Island?
With Expediaā€™s helpful filter tool, locating cheap villas in Shelter Island couldnā€™t be easier. To discover properties that are easy on your bank balance, refine your search by star rating, budget and amenities.