Compare Chester Villas

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

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

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

2 out of 5
Monroe NY
Guests staying at this villa enjoy a hot tub, laundry facilities, and barbecue grills.
Pool
Hot Tub
Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge

Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge

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, a garden, and barbecue grills.
Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC

Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC

Harriman NY
At this villa, guests have access to an arcade/game room, laundry facilities, and barbecue grills. This family-friendly villa also has a garden.
Pool
Kitchen
Luxury School House Retreat With Sauna & Pool- 1HR from NYC

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

New Hampton NY
$1,127 nightly
The price is $1,331 total per night
$1,331 total
Mar 3 - Mar 4
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.
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.
Family Retreat with Autumn Views and Game Room

Family Retreat with Autumn Views and Game Room

3 out of 5
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, a garden, and barbecue grills.
Pool
Hot Tub
Charming 3-bedroom villa with WiFi, AC in fabulous Monroe

Charming 3-bedroom villa with WiFi, AC in fabulous Monroe

Monroe NY
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has a garden.
Don't see what you're looking for?
See all available properties in Chester
View all properties
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
    $87 nightly
    The price is $103 total per night from Feb 28 to Mar 1
    $103 total
    Feb 28 - Mar 1
    Total with taxes and fees
    8.6/10 Excellent! (1,001 reviews)
    DoubleTree by Hilton Hotel Nanuet

    DoubleTree by Hilton Hotel Nanuet

    425 E Route 59 Nanuet NY
    $106 nightly
    The price is $123 total per night from Mar 22 to Mar 23
    $123 total
    Mar 22 - Mar 23
    Total with taxes and fees
    9/10 Wonderful! (1,079 reviews)
    Sonesta Simply Suites Nanuet

    Sonesta Simply Suites Nanuet

    20 Overlook Blvd Nanuet NY
    $92 nightly
    The price is $107 total per night from Feb 26 to Feb 27
    $107 total
    Feb 26 - Feb 27
    Total with taxes and fees
    8.4/10 Very Good! (1,108 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
$103
Highest Price
$1,331
Popular accommodation
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space, Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard, Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY., Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge, Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC, Luxury School House Retreat With Sauna & Pool- 1HR from NYC, Spacious Retreat w/ Pool, Hot Tub & Game Room, Family Retreat with Autumn Views and Game Room, Charming 3-bedroom villa with WiFi, AC in fabulous Monroe