Compare Chester Villas

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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
$1,140 nightly
The price is $1,347 total per night
$1,347 total
Jul 22 - Jul 23
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
Serene 10BR Retreat w/Pool, Gym & Hot Tub

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

Chester NY
$5,333 nightly
The price is $6,220 total per night
$6,220 total
Aug 9 - Aug 10
Total with taxes and fees
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 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
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
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, barbecue grills, and a garden.
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
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
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.

Monroe NY
Guests staying at this villa enjoy a hot tub, laundry facilities, and barbecue grills.
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
    $95 nightly
    The price is $117 total per night from Jul 26 to Jul 27
    $117 total
    Jul 26 - Jul 27
    Total with taxes and fees
    8.6/10 Excellent! (1,000 reviews)
    Spark by Hilton Fishkill

    Spark by Hilton Fishkill

    20 Schuyler Blvd Fishkill NY
    $89 nightly
    The price is $103 total per night from Aug 11 to Aug 12
    $103 total
    Aug 11 - Aug 12
    Total with taxes and fees
    8.4/10 Very Good! (180 reviews)
    Sleep Inn & Suites Middletown - Goshen

    Sleep Inn & Suites Middletown - Goshen

    3491 Route 6 Middletown NY
    $110 nightly
    The price is $130 total per night from Aug 11 to Aug 12
    $130 total
    Aug 11 - Aug 12
    Total with taxes and fees
    8.8/10 Excellent! (1,084 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
$103
Highest Price
$6,220
Popular accommodation
Luxury School House Retreat With Pool & Sauna - 1HR from NYC, Serene 10BR Retreat w/Pool, Gym & Hot Tub, 7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space, Magical Family Escape, Pool, HotTub, Pets, <1 Hr NYC, Pinnacle Pointe by Relaxtay | 600-Acre Private Luxury Estate with Spa, Pool, Theater & Lake, 11BR Retreat w Pool, Hot Tub, Sauna & Game Room, Spacious Retreat w/ Pool, Hot Tub & Game Room, Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard, Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.