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Compare 44 Villas in Shelter Island with updated reviews, rates, and availability.
![Pool](https://images.trvl-media.com/lodging/79000000/78310000/78302200/78302165/59911f29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
New Construction Greenport Pool House - 3 Blocks from Town
New Construction Greenport Pool House - 3 Blocks from Town
![Pool](https://images.trvl-media.com/lodging/67000000/66610000/66601900/66601802/7b72ceef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
10.0 out of 10, Exceptional, (1)
![Exterior](https://images.trvl-media.com/lodging/88000000/87140000/87138700/87138627/7e83e667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
10.0 out of 10, Exceptional, (17)
![Pool](https://images.trvl-media.com/lodging/106000000/105990000/105984800/105984778/4e0a6142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Villa Flasses
Villa Flasses
![Exterior](https://images.trvl-media.com/lodging/106000000/105960000/105958400/105958398/066129a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Villa Direen Modern East Hampton Villa
Villa Direen Modern East Hampton Villa
![Porch](https://images.trvl-media.com/lodging/36000000/35210000/35207100/35207060/fa3ae3e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Villa Spectrum
Villa Spectrum
![Outdoor pool](https://images.trvl-media.com/lodging/107000000/106020000/106017700/106017638/95d52820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Villa Edwards Hole
Villa Edwards Hole
![Exterior](https://images.trvl-media.com/lodging/96000000/95670000/95664200/95664188/e8bebd72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Amagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach
Amagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach
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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![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Montauk Manor
Montauk Manor
9.2 out of 10, Wonderful, (1111)
The price is AED 481
AED 621 total
includes taxes & fees
18 Feb - 19 Feb
![Front of property](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/478145f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Montauk Oceanside Suites
Montauk Oceanside Suites
8.4 out of 10, Very Good, (361)
The price is AED 412
AED 507 total
includes taxes & fees
27 Feb - 28 Feb
![Property grounds](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/6c503dde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Windward Shores Ocean Resort
Windward Shores Ocean Resort
8.8 out of 10, Excellent, (271)
The price is AED 484
AED 632 total
includes taxes & fees
18 Feb - 19 Feb
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.
Recent reviews of Shelter Island hotels
Recent reviews of Shelter Island hotels
![Water's Edge Resort & Spa](http://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg)
Water's Edge Resort & Spa
5/5 Excellent
"I love this property! I stayed for one night and there was a comedian and a lot of activity in the hotel which made for a great night!
My only complaint is the bed! It was probably the least comfortable bed I have ever slept in a hotel.
I had a horrible night sleep as the mattress was terrible! The room and amenities are all top notch! I am not a fan of the blue toilet water as a cleaner… but just my personal opinion. "
A verified traveler stayed at Water's Edge Resort & Spa
Posted 2 days ago
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