Villas in Chester

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Find vacation rentals that suit your style

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Apartments
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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Chester villas

A large, multi-story house with a prominent stone chimney, multiple windows, and a well-maintained garden.

1. Spectacular Historic Mansion w/Pool&Tennis

Spectacular Historic Mansion w/Pool&Tennis
Goshen
10.0 out of 10, Exceptional, (20 reviews)
"Truly amazing house, incredible pool, easy renting experience. Would definitely be back. "
United States
Aditya U.
$2,440 nightly
The price is $2,552
Nov 8 - Nov 9
Total with taxes and fees
Spectacular Historic Mansion w/Pool&Tennis
A staircase leading to a porch with a view of a house and surrounding trees.

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, (23 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.
$1,086 nightly
The price is $1,283
Nov 10 - Nov 11
Total with taxes and fees
Luxury School House Retreat With Pool & Sauna - 1HR from NYC
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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Learn more about Chester

Lace up your hiking boots and hit the trails at Goosepond Mountain State Park for stunning views. After working up an appetite, head to Castle Fun Center for go-karts, mini-golf, and arcade games.

See all hotels in Chester
A bridge with a plaque reading "City of Chester Queens Park Bridge 1923".

Top reviews in Chester

A Fairfield Inn & Suites hotel with a stone facade, a covered entrance, and a parking lot.
Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
Goshen

10/10 Excellent

Stayed overdoing the memorial day weekend after visiting Legoland. The hotel was pretty full judging from all the people at breakfast, no complaints this was a very convenient hotel would definitely come back again!
United States
jonathan
Reviewed May 30, 2024
Fairfield Inn & Suites by Marriott Goshen Middletown

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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