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Our top choices for Chester villas
1. Spectacular Historic Mansion w/Pool&Tennis
Spectacular Historic Mansion w/Pool&TennisGoshen
10.0 out of 10, Exceptional, (20 reviews)
10/10
Exceptional
(20 reviews)
"Truly amazing house, incredible pool, easy renting experience. Would definitely be back. "
"Truly amazing house, incredible pool, easy renting experience. Would definitely be back. "
Aditya U.
$2,373 nightly
The price is $2,485
$2,485 total
Nov 8 - Nov 9
Total with taxes and fees
2. Luxury School House Retreat With Pool & Sauna - 1HR from NYC
Luxury School House Retreat With Pool & Sauna - 1HR from NYCNew Hampton
10.0 out of 10, Exceptional, (23 reviews)
10/10
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! "
"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! "Jennifer P.
$1,056 nightly
The price is $1,247
$1,247 total
Nov 10 - Nov 11
Total with taxes and fees
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.
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.
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.
Top reviews in Chester
Fairfield Inn & Suites by Marriott Goshen Middletown
Fairfield Inn & Suites by Marriott Goshen MiddletownGoshen
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!
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!
jonathan
The Dominion House Bed & Breakfast
The Dominion House Bed & BreakfastChester
10/10 Excellent
Lovely period home. Owners were friendly, courteous and informative. Breakfast was delicious. Overall stay was very enjoyable and would stay again.
Lovely period home. Owners were friendly, courteous and informative. Breakfast was delicious. Overall stay was very enjoyable and would stay again.
Cindy
La Quinta Inn & Suites by Wyndham Middletown-Goshen
La Quinta Inn & Suites by Wyndham Middletown-GoshenMiddletown
10/10 Excellent
I loved how clean my room was. It was simple but had everything you needed. It was very quiet and I didn’t not hear anything from outside my room while I was in there.
I loved how clean my room was. It was simple but had everything you needed. It was very quiet and I didn’t not hear anything from outside my room while I was in there.
Jordan
Tru by Hilton Middletown
Tru by Hilton MiddletownMiddletown
10/10 Excellent
Love coming to this hotel, it has a wonderful atmosphere, caring staff and the environment is throughly clean and friendly. Saxida is very lovley and accommodating she definitely cares about the guests that come in and any problems that may occur she is urgent to fix it I appreciate how she remembered who I was and her energy is full of light. I appreciate everything this hotel has to offer and will be returning to make more fun memories in the future!
Love coming to this hotel, it has a wonderful atmosphere, caring staff and the environment is throughly clean and friendly. Saxida is very lovley and accommodating she definitely cares about the guests that come in and any problems that may occur she is urgent to fix it I appreciate how she remembered who I was and her energy is full of light. I appreciate everything this hotel has to offer and will be returning to make more fun memories in the future!
Daniela
Holiday Inn Express & Suites Middletown - Goshen by IHG
Holiday Inn Express & Suites Middletown - Goshen by IHGMiddletown
10/10 Excellent
We liked everything about the hotel!
The room was clean, breakfast was delicious, the staff was so friendly!
We can't say enough nice things about the hotel!
We liked everything about the hotel!
The room was clean, breakfast was delicious, the staff was so friendly!
We can't say enough nice things about the hotel!
Kathleen
Candlewood Suites Middletown Goshen by IHG
Candlewood Suites Middletown Goshen by IHGMiddletown
10/10 Excellent
Very Good
Very Good
Moraivic
Hampton Inn by Hilton Middletown
Hampton Inn by Hilton MiddletownMiddletown
10/10 Excellent
10/10! Super close to whatever you need, comfy beds and beautiful atmosphere. Perfect place to bring the kids after Legoland 😁
10/10! Super close to whatever you need, comfy beds and beautiful atmosphere. Perfect place to bring the kids after Legoland 😁
Destiny
The Orange Inn Boutique Hotel
The Orange Inn Boutique HotelGoshen
10/10 Excellent
Well maintained and clean property , inside and out. We could have gotten more of an overview of the property when we checked in, but we managed. Ample parking available in their parking lot in the back. One thing I was surprised about -for a luxury inn , they had polyester sheets instead of cotton sheets. Overall great stay.
Well maintained and clean property , inside and out. We could have gotten more of an overview of the property when we checked in, but we managed. Ample parking available in their parking lot in the back. One thing I was surprised about -for a luxury inn , they had polyester sheets instead of cotton sheets. Overall great stay.
Kevin
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - GoshenMiddletown
10/10 Excellent
The stay was great friendly service as usual. The person who checked me in was nice kind and very professional. Don’t let me get started on my room so Extravagant and put together. Didn’t want to get out of my shower all and breakfast (NY) Forgetaboutit Awesomeness.
The stay was great friendly service as usual. The person who checked me in was nice kind and very professional. Don’t let me get started on my room so Extravagant and put together. Didn’t want to get out of my shower all and breakfast (NY) Forgetaboutit Awesomeness.
Damion
Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown GoshenMiddletown
10/10 Excellent
We only stayed one night, but we will be back. It seemed like a really nice place with more to offer than surrounding hotels.
We only stayed one night, but we will be back. It seemed like a really nice place with more to offer than surrounding hotels.
Kathleen
Residence Inn by Marriott Middletown Goshen
Residence Inn by Marriott Middletown GoshenMiddletown
10/10 Excellent
Everything was beautiful, it looks like a new property. My only complaint was after shutting off the air conditioner/heater it still remained on and was very noisy keeping my wife and I up most of the night. Even switching the circuit breaker off didn’t solve the problem.
I’m not one to complain though and didn’t bother the staff at the late hour. I still wouldn’t hesitate to stay at a residence inn property in the future.
Everything was beautiful, it looks like a new property. My only complaint was after shutting off the air conditioner/heater it still remained on and was very noisy keeping my wife and I up most of the night. Even switching the circuit breaker off didn’t solve the problem.
I’m not one to complain though and didn’t bother the staff at the late hour. I still wouldn’t hesitate to stay at a residence inn property in the future.
Joseph
Holiday Inn Express & Suites Montgomery by IHG
Holiday Inn Express & Suites Montgomery by IHGMontgomery
10/10 Excellent
Great stay
Great stay
Marissa
Home2 Suites by Hilton Middletown
Home2 Suites by Hilton MiddletownMiddletown
10/10 Excellent
Loved the large spacious and well laid out room. Breakfast was great but the space was a bit crowded.
Loved the large spacious and well laid out room. Breakfast was great but the space was a bit crowded.
Anonymous traveler
Borland House Inn
Borland House InnMontgomery
10/10 Excellent
Lovely place. Very special, can’t wait to return.
Lovely place. Very special, can’t wait to return.
Kate
Frequently Asked Questions
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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.