Compare Chester Villas

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Featured Villas in Chester

Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

Chester NY
Guests of this villa enjoy features like an outdoor pool, a gym, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities and a garden.
Pool
Kitchen
Magical Family Escape, Pool, HotTub, Pets, <1 Hr NYC

Magical Family Escape, Pool, HotTub, Pets, <1 Hr NYC

Harriman NY
This villa features a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly villa include a garden and barbecue grills.
Pool
Hot Tub
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

Monroe NY
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. This smoke-free villa also has barbecue grills.
Pool
Hot Tub
Pinnacle Pointe by Relaxtay | 600-Acre Private Luxury Estate with Spa, Pool, Theater & Lake

Pinnacle Pointe by Relaxtay | 600-Acre Private Luxury Estate with Spa, Pool, Theater & Lake

Middletown NY
This villa offers a gym, a sauna, and a hot tub. Other amenities at this family-friendly villa include an arcade/game room, a garden, and barbecue grills.
Pool
Hot Tub
11BR Retreat w Pool, Hot Tub, Sauna & Game Room

11BR Retreat w Pool, Hot Tub, Sauna & Game Room

Chester NY
Guests of this villa enjoy features like an outdoor pool, a gym, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities and barbecue grills.
Pool
Kitchen
Luxury 10BR w/Pool, Hot Tub & Pizza Oven

Luxury 10BR w/Pool, Hot Tub & Pizza Oven

Stony Point NY
Guests of this villa enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, barbecue grills, and a garden.
Pool
Hot Tub
Serene 10BR Retreat w/Pool, Gym & Hot Tub

Serene 10BR Retreat w/Pool, Gym & Hot Tub

Chester NY
Guests staying at this villa enjoy an outdoor pool, a gym, and a hot tub. Other amenities at this family-friendly villa include an arcade/game room, laundry facilities, and a garden.
Pool
Hot Tub
Spacious Retreat w/ Pool, Hot Tub & Game Room

Spacious Retreat w/ Pool, Hot Tub & Game Room

Stony Point NY
At this villa, guests have access to features like laundry facilities.
Pool
Washer
Luxury School House Retreat With Pool & Sauna - 1HR from NYC

Luxury School House Retreat With Pool & Sauna - 1HR from NYC

New Hampton NY
$1,128 nightly
The price is $1,332 total per night
$1,332 total
Aug 25 - Aug 26
Total with taxes and fees
This villa features ski-in/ski-out access, an outdoor pool, and a gym. Other amenities at this ski villa include a sauna, an arcade/game room, and laundry facilities.
Pool
Kitchen
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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 Chester

    Holiday Inn Express Hotel & Suites Chester by IHG

    Holiday Inn Express Hotel & Suites Chester by IHG

    2 Bryle Place Chester NY
    $122 nightly
    The price is $150 total per night from Aug 30 to Aug 31
    $150 total
    Aug 30 - Aug 31
    Total with taxes and fees
    8.6/10 Excellent! (1,015 reviews)
    Crowne Plaza Suffern - Mahwah by IHG

    Crowne Plaza Suffern - Mahwah by IHG

    3 Executive Blvd Suffern NY
    $125 nightly
    The price is $145 total per night from Sep 3 to Sep 4
    $145 total
    Sep 3 - Sep 4
    Total with taxes and fees
    9/10 Wonderful! (1,030 reviews)
    Sleep Inn & Suites Middletown - Goshen

    Sleep Inn & Suites Middletown - Goshen

    3491 Route 6 Middletown NY
    $106 nightly
    The price is $126 total per night from Sep 10 to Sep 11
    $126 total
    Sep 10 - Sep 11
    Total with taxes and fees

Luxury Villas

Book luxury villas in Chester
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Chester. 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 Chester, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Chester
You won’t have a problem finding your own space in Chester. 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 Chester on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Chester 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!

Chester Villas essential information

Accommodation
14 Villas
Lowest Price
$126
Highest Price
$1,332
Popular accommodation
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard, Magical Family Escape, Pool, HotTub, Pets, <1 Hr NYC, 7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space, Pinnacle Pointe by Relaxtay | 600-Acre Private Luxury Estate with Spa, Pool, Theater & Lake, 11BR Retreat w Pool, Hot Tub, Sauna & Game Room, Luxury 10BR w/Pool, Hot Tub & Pizza Oven, Serene 10BR Retreat w/Pool, Gym & Hot Tub, Spacious Retreat w/ Pool, Hot Tub & Game Room, Luxury School House Retreat With Pool & Sauna - 1HR from NYC