Book Villas in Shelter Island, NY
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top Villas in Shelter Island
New Construction Greenport Pool House - 3 Blocks from Town
Greenport NY
$1,308 nightly
The price is $1,494 total per night
$1,494 total
May 27 - May 28
Total with taxes and fees
This villa features an outdoor pool and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Hampton Private Retreat - last minute offer June 23-
Southampton NY
This villa features a gym and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Luxe Hamptons Retreat ✨ Pool + Hot Tub • Sleeps 10 • Near Southampton & US Open
Hampton Bays NY
This villa features a gym and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Iconic Charles Moore Springs home with dock and our home is pet-friendly
East Hampton NY
This villa featured laundry facilities and barbecue grills.
Washer
Dryer
Southampton Paradise with Saltwater Pool & Spa & 3 minutes to Best Beach in USA
Southampton NY
This villa features an outdoor pool and a gym. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.
Pool
Hot Tub
Live on the Water: Dock, Beach, Boat, Kayak & Fish
Southampton NY
This villa features a gym and a hot tub. Families will appreciate the playground and onsite laundry facilities. A garden, concierge services, and barbecue grills are also on offer.
Hot Tub
Kitchen
Villa Direen Modern East Hampton Villa
137 Stephen Hands Path East Hampton NY
An outdoor pool, free self parking, and barbecue grills are featured at this villa. A garden and a picnic area are also provided.
Pool
Washer
Villa Flasses
94 Spring Pond Ln Southampton NY
An outdoor pool, free self parking, and barbecue grills are featured at this villa. A garden, a picnic area, and a virtual front desk are also on offer.
Pool
Parking included
PinkWood PlayHouse
24 Woodpink Dr East Hampton NY
This villa features a seasonal outdoor pool and a hot tub. Business travelers can take advantage of the free WiFi in public areas. Free self parking and a picnic area are also offered on site.
Pool
Hot Tub
MODERN 5 BEDROOM MONTAUK BEACH HOME
Montauk NY
An outdoor pool is featured at this villa, along with a garden and laundry facilities. Families will appreciate the arcade/game room and barbecue grills.
Pool
Kitchen
Villa Skylar
Montauk Highway Southampton NY
An outdoor pool, free parking, and laundry facilities are featured at this villa. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a picnic area, and dry cleaning are also on offer.
Pool
Kitchen
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.
Top hotels in Shelter Island
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
$164 nightly
The price is $187 total per night from Apr 30 to May 1
$187 total
Apr 30 - May 1
Total with taxes and fees
9.6/10 Exceptional! (473 reviews)
Shelter Island Villas essential information
Accommodation | 38 Villas |
|---|---|
Lowest Price | $136 |
Highest Price | $1,494 |
Popular accommodation | New Construction Greenport Pool House - 3 Blocks from Town, Hampton Private Retreat - last minute offer June 23-, Luxe Hamptons Retreat ✨ Pool + Hot Tub • Sleeps 10 • Near Southampton & US Open, Iconic Charles Moore Springs home with dock and our home is pet-friendly, Southampton Paradise with Saltwater Pool & Spa & 3 minutes to Best Beach in USA, Live on the Water: Dock, Beach, Boat, Kayak & Fish, Villa Direen Modern East Hampton Villa, Villa Flasses, PinkWood PlayHouse, MODERN 5 BEDROOM MONTAUK BEACH HOME, Villa Skylar, Villa Nostro Palazzo |