Compare Chester Villas

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Featured Villas in Chester

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
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, Luxury Estate - 1 Hr NYC - Weddings

Magical Family Escape, Pool, HotTub, Pets, Luxury Estate - 1 Hr NYC - Weddings

Harriman NY
This villa features a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly villa include barbecue grills and a garden.
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
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.
Luxury School House Retreat With Pool & Sauna - 1HR from NYC

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

New Hampton NY
$1,142 nightly
The price is $1,349 total per night
$1,349 total
Jun 9 - Jun 10
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
Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

Monroe NY
Guests staying at this villa enjoy a hot tub, laundry facilities, and barbecue grills.
Pool
Hot Tub
Modern Villa with private pond near Legoland and Delaware River.

Modern Villa with private pond near Legoland and Delaware River.

Port Jervis NY
At this villa, guests have access to features like laundry facilities.
Washer
Dryer
Group Retreat w. Backyard, BBQ, Gym, Games & More!

Group Retreat w. Backyard, BBQ, Gym, Games & More!

Stony Point NY
Guests of this villa enjoy features like a gym, 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
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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
    $127 nightly
    The price is $156 total per night from Jun 14 to Jun 15
    $156 total
    Jun 14 - Jun 15
    Total with taxes and fees
    8.6/10 Excellent! (1,004 reviews)
    Spark by Hilton Fishkill

    Spark by Hilton Fishkill

    20 Schuyler Blvd Fishkill NY
    $93 nightly
    The price is $107 total per night from Jun 30 to Jul 1
    $107 total
    Jun 30 - Jul 1
    Total with taxes and fees
    8.2/10 Very Good! (117 reviews)
    DoubleTree by Hilton Hotel Nanuet

    DoubleTree by Hilton Hotel Nanuet

    425 E Route 59 Nanuet NY
    $130 nightly
    The price is $152 total per night from Jun 21 to Jun 22
    $152 total
    Jun 21 - Jun 22
    Total with taxes and fees
    9/10 Wonderful! (1,143 reviews)

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
23 Villas
Lowest Price
$107
Highest Price
$1,349
Popular accommodation
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space, Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard, Magical Family Escape, Pool, HotTub, Pets, Luxury Estate - 1 Hr NYC - Weddings, Pinnacle Pointe by Relaxtay | 600-Acre Private Luxury Estate with Spa, Pool, Theater & Lake, Spacious Retreat w/ Pool, Hot Tub & Game Room, Luxury School House Retreat With Pool & Sauna - 1HR from NYC, Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY., Modern Villa with private pond near Legoland and Delaware River. , Group Retreat w. Backyard, BBQ, Gym, Games & More!