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

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

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

New Hampton NY
$1,104 nightly
The price is $1,304 total per night
$1,304 total
Jun 30 - Jul 1
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.
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.
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.
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 barbecue grills and a garden.
11BR Retreat w Pool & Game Room

11BR Retreat w Pool & Game Room

Chester NY
$3,293 nightly
The price is $3,845 total per night
$3,845 total
Jul 1 - Jul 2
Total with taxes and fees
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.
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.
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.
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
    $115 nightly
    The price is $142 total per night from Jul 2 to Jul 3
    $142 total
    Jul 2 - Jul 3
    Total with taxes and fees
    8.6/10 Excellent! (1,001 reviews)
    Spark by Hilton Fishkill

    Spark by Hilton Fishkill

    20 Schuyler Blvd Fishkill NY
    $93 nightly
    The price is $107 total per night from Jul 6 to Jul 7
    $107 total
    Jul 6 - Jul 7
    Total with taxes and fees
    8.2/10 Very Good! (144 reviews)
    Overlook Lodge at Bear Mountain

    Overlook Lodge at Bear Mountain

    55 Hessian Drive Bear Mountain NY
    $142 nightly
    The price is $175 total per night from Jul 1 to Jul 2
    $175 total
    Jul 1 - Jul 2
    Total with taxes and fees
    8.4/10 Very Good! (1,004 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
14 Villas
Lowest Price
$107
Highest Price
$3,845
Popular accommodation
Luxury School House Retreat With Pool & Sauna - 1HR from NYC, Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard, 7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space, Pinnacle Pointe by Relaxtay | 600-Acre Private Luxury Estate with Spa, Pool, Theater & Lake, Magical Family Escape, Pool, HotTub, Pets, <1 Hr NYC, 11BR Retreat w Pool & Game Room, Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge, Serene 10BR Retreat w/Pool, Gym & Hot Tub, Spacious Retreat w/ Pool, Hot Tub & Game Room