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

Warm Escape, Wood Stove, 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
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.
Washer
Dryer
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
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, barbecue grills, and a garden.
Pool
Hot Tub
Grand 10BR Retreat w/Pool & Hot Tub

Grand 10BR Retreat w/Pool & Hot Tub

Chester 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.
Pool
Hot Tub
Luxury School House Retreat With Sauna & Pool- 1HR from NYC

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

New Hampton NY
$1,142 nightly
The price is $1,349 total per night
$1,349 total
Apr 14 - Apr 15
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
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
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
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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
    $112 nightly
    The price is $132 total per night from Apr 14 to Apr 15
    $132 total
    Apr 14 - Apr 15
    Total with taxes and fees
    8.6/10 Excellent! (1,005 reviews)
    DoubleTree by Hilton Hotel Nanuet

    DoubleTree by Hilton Hotel Nanuet

    425 E Route 59 Nanuet NY
    $114 nightly
    The price is $133 total per night from Apr 26 to Apr 27
    $133 total
    Apr 26 - Apr 27
    Total with taxes and fees
    9/10 Wonderful! (1,097 reviews)
    Sonesta Simply Suites Nanuet

    Sonesta Simply Suites Nanuet

    20 Overlook Blvd Nanuet NY
    $97 nightly
    The price is $113 total per night from Apr 19 to Apr 20
    $113 total
    Apr 19 - Apr 20
    Total with taxes and fees
    8.4/10 Very Good! (1,161 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
$113
Highest Price
$1,349
Popular accommodation
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space, Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC, Spacious Retreat w/ Pool, Hot Tub & Game Room, Pinnacle Pointe by Relaxtay | 600-Acre Private Luxury Estate with Spa, Pool, Theater & Lake, Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge, Grand 10BR Retreat w/Pool & Hot Tub, Luxury School House Retreat With Sauna & Pool- 1HR from NYC, Group Retreat w. Backyard, BBQ, Gym, Games & More!, Modern Villa with private pond near Legoland and Delaware River.