A green agricultural field with rows of crops and greenhouses in the distance under a cloudy sky.

Villas in Chester

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Chester villas

Outdoor spa tub

1. 11BR Retreat w Pool, Hot Tub, Sauna & Game Room

11BR Retreat w Pool, Hot Tub, Sauna & Game Room
Chester
10.0 out of 10, Exceptional, (2 reviews)
"5 star experience! We will definitely stay here again. The host was responsive, and the house was in perfect condition. The pool was clean. The sauna was spotless!"
United States
Benny P.
$2,901 nightly
The price is $3,382
Sep 27 - Sep 28
Total with taxes and fees
11BR Retreat w Pool, Hot Tub, Sauna & Game Room
Property grounds

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

Luxury School House Retreat With Pool & Sauna - 1HR from NYC
New Hampton
10.0 out of 10, Exceptional, (22 reviews)
"House was great, conveniently located to ski mountain, Hunter was a pleasure to work with, house was clean and had so many amenities for our family! Highly recommend! "
United States
Jennifer P.
$1,142 nightly
The price is $1,349
Sep 22 - Sep 23
Total with taxes and fees
Luxury School House Retreat With Pool & Sauna - 1HR from NYC
Exterior

3. Luxury 10BR w/Pool, Hot Tub & Pizza Oven

Luxury 10BR w/Pool, Hot Tub & Pizza Oven
Stony Point
5.0 out of 10, (2 reviews)
"The house itself was beautiful, spacious, clean, and overall a very comfortable place to stay. There were many things we really liked about the property.Unfortunately, we did have some issues during our stay. Communication with the host was not very prompt. We had an issue with the basement AC not cooling sufficiently, and when we reached out for help with the thermostat, the host was unable to guide us and ultimately did not follow up.The bigger concern was the pool. It was not simply a matter...
United States
Brian R.
$3,900 nightly
The price is $4,327
Oct 12 - Oct 13
Total with taxes and fees
Luxury 10BR w/Pool, Hot Tub & Pizza Oven
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.
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Top Chester Hotel Reviews

The Thayer Hotel at West Point

The Thayer Hotel at West Point

10/10 Excellent
"Lovely place with a great restaurant and dining room!!"
Doyle 1-night trip
Posted 1 hour ago
The Thayer Hotel at West Point

Find out more about Chester

Chester Villas information

Number of reviews
24
Accommodation
12 Villas
Lowest Price
$1,349
Highest Price
$4,327

Frequently asked questions

Why book your villa in Chester with Expedia?
Expedia makes it simple to find your dream villa in Chester. Vacationing with the kids? Make the most of our helpful filters to look for stays with a kitchen or a pool. If you have a certain budget, select how much you'd like to spend and your preferred star rating. We'll help you find the perfect fit that gels with your style and taste.
How can I find cheap villas in Chester?
Expedia is here to help you easily source cheap villas in Chester. Use our handy filter tool to choose amenities, budget and star rating to refine your search and find an amazing place to stay in a few clicks.
What is there to do near my villa in Chester?
If you're ready to make the most of your time in Chester, pay a visit to Castle Fun Center. It's a favorite with locals and travelers alike.

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