Compare Shelter Island Heights Villas

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Featured Villas in Shelter Island Heights

Spacious Oceanview Villa (Sleeps 22)

Spacious Oceanview Villa (Sleeps 22)

$846 nightly
The price is $957 total per night
$957 total
Oct 7 - Oct 8
Total with taxes and fees
At this villa, guests have access to an arcade/game room, laundry facilities, and a garden. Other amenities at this beach villa include a water dispenser and barbecue grills.
Pool
Kitchen
Hampton Private Retreat - last minute offer June 23-

Hampton Private Retreat - last minute offer June 23-

Guests of this villa enjoy features like a gym, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.
Pool
Hot Tub
New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town

Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.
Pool
Hot Tub
Waterfront Holiday Vacation Villa New England - 2 min from Ocean W/ fireplace

Waterfront Holiday Vacation Villa New England - 2 min from Ocean W/ fireplace

At this villa, guests have access to laundry facilities, local meal delivery service, and barbecue grills. This smoke-free villa also has a garden.
Kitchen
Washer
Southampton Paradise with Saltwater Pool & Spa & 3 minutes to Best Beach in USA

Southampton Paradise with Saltwater Pool & Spa & 3 minutes to Best Beach in USA

At this villa, guests enjoy an outdoor pool, a gym, and a hot tub. Additional amenities include an arcade/game room, laundry facilities, and barbecue grills.
Pool
Hot Tub
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

Guests staying at this villa enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free villa also has a garden.
Pool
Hot Tub
Iconic Charles Moore Springs home with dock and our home is pet-friendly

Iconic Charles Moore Springs home with dock and our home is pet-friendly

2 out of 5
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has barbecue grills.
Washer
Dryer
Villa Direen Modern East Hampton Villa

Villa Direen Modern East Hampton Villa

3.5 out of 5
137 Stephen Hands Path, East Hampton, NY
Guests staying at this villa can enjoy an outdoor pool, barbecue grills, and a picnic area. You can take advantage of free parking, along with an airport shuttle (available on request) for USD 200 per vehicle. This villa also has a garden.
Pool
Washer
Villa Flasses

Villa Flasses

3 out of 5
94 Spring Pond Ln, Southampton, NY
Guests staying at this villa can enjoy an outdoor pool, a picnic area, and a garden. There's free parking, and an airport shuttle (available on request) for USD 200 per vehicle. This villa also has barbecue grills.
Pool
Parking included
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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.

Hotel Options in Shelter Island Heights

    The Pridwin Hotel

    The Pridwin Hotel

    81 Shore Road, Shelter Island Heights, NY
    $406 nightly
    The price is $464 total per night from Oct 12 to Oct 13
    $464 total
    Oct 12 - Oct 13
    Total with taxes and fees
    9.4/10 Exceptional! (79 reviews)
    The Chequit

    The Chequit

    23 Grand Ave, Shelter Island Heights, NY
    $431 nightly
    The price is $493 total per night from Oct 7 to Oct 8
    $493 total
    Oct 7 - Oct 8
    Total with taxes and fees
    8.8/10 Excellent! (36 reviews)
    Pier Blue Inn Old Saybrook - Essex

    Pier Blue Inn Old Saybrook - Essex

    1430 Boston Post Rd, Old Saybrook, CT
    $89 nightly
    The price is $102 total per night from Oct 7 to Oct 8
    $102 total
    Oct 7 - Oct 8
    Total with taxes and fees
    7.8/10 Good! (1,003 reviews)

Luxury Villas

Book luxury villas in Shelter Island Heights
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Shelter Island Heights. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Shelter Island Heights, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Shelter Island Heights
You won’t have a problem finding your own space in Shelter Island Heights. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Shelter Island Heights on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Shelter Island Heights rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Shelter Island Heights Villas essential information

Accommodation
42 Villas
Lowest Price
$102
Highest Price
$957
Popular accommodation
Spacious Oceanview Villa (Sleeps 22), Hampton Private Retreat - last minute offer June 23-, New Construction Greenport Pool House - 3 Blocks from Town, Waterfront Holiday Vacation Villa New England - 2 min from Ocean W/ fireplace , Southampton Paradise with Saltwater Pool & Spa & 3 minutes to Best Beach in USA, Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach, Iconic Charles Moore Springs home with dock and our home is pet-friendly, Villa Direen Modern East Hampton Villa, Villa Flasses