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Our top choices for Chester vacation rentals
1. Historic Horse Barn Apartment in Goshen
Historic Horse Barn Apartment in Goshen3.5 star property
Goshen
2. Hudson Valley Retreat w/ Pool Near Greenwood Lake
Hudson Valley Retreat w/ Pool Near Greenwood Lake3.0 star property
Monroe
10.0 out of 10, Exceptional, (4 reviews)
10/10
Exceptional
(4 reviews)
"The house was very quiet and exactly as advertised. Would stay again!"
"The house was very quiet and exactly as advertised. Would stay again!"
Scott
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.
Find vacation rentals that suit your style
Top Chester Hotel Reviews
Holiday Inn Express Hotel & Suites Chester by IHG
Holiday Inn Express Hotel & Suites Chester by IHGChester
10/10 Excellent
The hotel is new so everything is fresh, clean and beautiful. My husband and I are retired seniors and loved the fact that it was only a shower. Often a tub does not have a rough surface on the bottom to prevent slipping. So the shower was just perfect. We were upgraded to a suite that was just gorgeous. Could not have been better.
The hotel is new so everything is fresh, clean and beautiful. My husband and I are retired seniors and loved the fact that it was only a shower. Often a tub does not have a rough surface on the bottom to prevent slipping. So the shower was just perfect. We were upgraded to a suite that was just gorgeous. Could not have been better.
Jeris
Sleep Inn & Suites Monroe - Woodbury
Sleep Inn & Suites Monroe - WoodburyMonroe
10/10 Excellent
Everything was great! From the actual rooms to the delicious breakfast served every morning.
Everything was great! From the actual rooms to the delicious breakfast served every morning.
Lisyani
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
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
Everything was great 😊
Everything was great 😊
NIGEL
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
Candlewood Suites Middletown Goshen by IHG
Candlewood Suites Middletown Goshen by IHGMiddletown
10/10 Excellent
Very Good
Very Good
Moraivic
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
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
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
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
Homewood Suites Stewart Airport
Homewood Suites Stewart AirportNew Windsor
10/10 Excellent
Needed a place to stay when moving to the area. This hotel was conveniently located and very affordable - especially considering what you get! The suites were fantastic - spacious, everything we needed, kitchenettes. On top of that they serve a good hot breakfast every morning and a manager's reception (which is essentially a meal) four nights a week. What a deal! Friendly, helpful staff too. I truly don't have anything negative to say about this hotel.
Needed a place to stay when moving to the area. This hotel was conveniently located and very affordable - especially considering what you get! The suites were fantastic - spacious, everything we needed, kitchenettes. On top of that they serve a good hot breakfast every morning and a manager's reception (which is essentially a meal) four nights a week. What a deal! Friendly, helpful staff too. I truly don't have anything negative to say about this hotel.
Anonymous traveler
High Point Motel
High Point MotelSussex
10/10 Excellent
Melanie from HP was awesome! The room was super clean and recently updated.
Melanie was super nice and sent me a message telling me I left some personal items behind. Thank you!
Melanie from HP was awesome! The room was super clean and recently updated.
Melanie was super nice and sent me a message telling me I left some personal items behind. Thank you!
Oswald
Find out more about Chester
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Frequently Asked Questions
Are there vacation rentals in Chester?
Yes, you can find vacation rentals in Chester close to Castle Fun Center, or you can go with a more remote option if you'd like a relaxing place to stay. The shops and restaurants are several reasons why visitors like Chester. Make sure you have time to check out the ski areas and coffeehouses during your trip.
How many vacation rentals are there in Chester?
Expedia has 11 vacation rentals for your stay in Chester.
What can I see and do in Chester?
Cultural attractions include Museum Village and Sugar Loaf Performing Arts Center, whereas The Rock Sports Complex is one spot to enjoy nature. While here, Castle Fun Center and Goosepond Mountain State Park are other places worth a visit.
What are vacation rentals like in Chester?
Vacation rentals are privately owned properties you can reserve for several days or more in Chester. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.