Chester, NY

Travel Guide

A green agricultural field with rows of crops and greenhouses in the distance under a cloudy sky.
A bridge with a plaque reading "City of Chester Queens Park Bridge 1923".
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
2 Bryle Place Chester NY
$105 nightly
The price is $129 total per night from Sep 24 to Sep 25
$129 total
Sep 24 - Sep 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Holiday Inn Express Hotel & Suites Chester by IHG
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
$111 nightly
The price is $137 total per night from Oct 18 to Oct 19
$137 total
Oct 18 - Oct 19
Total with taxes and fees
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (1,002 reviews)
"It is a very nice place .To bad the pool was not open ."

Reviewed on Sep 17, 2026

Overlook Lodge at Bear Mountain
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
$113 nightly
The price is $133 total per night from Oct 12 to Oct 13
$133 total
Oct 12 - Oct 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Sleep Inn & Suites Middletown - Goshen
See all 1,075 properties in Chester
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.
Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

Chester NY
Stay at this vacation home in Chester. Enjoy free WiFi, a garden, and patios. Popular attractions LEGOLAND® New York and Sugar Loaf Performing Arts Center are ...
9/10 Wonderful! (2 reviews)
"We had a great stay! The house was nice, clean, and comfortable, and everything was as expected. The host was also very responsive and easy to communicate with. We did have a small issue during our stay (our fault), but the host addressed it promptly and made sure it was taken care of. Overall, we ..."

Reviewed on Sep 8, 2026

Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8
1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen

Fishkill NY
Stay at this apartment in Fishkill. Enjoy free WiFi, cable/satellite TV service, and air conditioning. Popular attractions Van Wyck Homestead Museum and Fishkill ...
8.8/10 Excellent! (20 reviews)
Do not stay here. It’s a motel 6 that is very dirty. It was so bad I had to bo ...
"Do not stay here. It’s a motel 6 that is very dirty. It was so bad I had to book at another location so do not believe any of the positive reviews. To make it worse the hotel was overbooked. Very misleading listing. Horrible place and not safe."

Reviewed on Sep 12, 2026

1 Queen Bed | Non-Smoking, Kitchen
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery NY
Stay at this cottage in Fort Montgomery. Enjoy free WiFi, a garden, and patios. Popular attractions Bear Mountain State Park and Manitoga The Russel Wright Design ...
9.8/10 Exceptional! (145 reviews)
"It was a beautiful view with kind and friendly hosts. I would recommend this listing to anyone!"

Reviewed on Aug 31, 2026

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
See all properties in Chester
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.

Stay near popular Chester attractions

Castle Fun Center

8.2/10 (29 reviews)
You can take time to visit Castle Fun Center during your travels to Chester. While you're in the area, find time to visit its shops.
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Frequently asked questions

Is Chester worth visiting?
Chester is worth visiting for its diverse dining scene, offering delicious Italian and North American cuisine. Travelers will also find entertainment at standout attractions such as the Castle Fun Center and The Rock Sports Complex, providing fun experiences for all ages.
When is the best time to visit Chester?
The best time to visit Chester is from May through September, when the weather is typically mild and enjoyable for exploring. For travelers seeking fewer crowds and better value, the cooler months of December through March offer a more tranquil experience, often with winter scenery.
What is Chester known for?
Chester is known for its family-friendly entertainment and sports facilities, such as Castle Fun Center and The Rock Sports Complex. Travelers can also enjoy performances at the Sugar Loaf Performing Arts Center and explore a local Italian food culture.
What is a good itinerary length for Chester?
A good itinerary length for Chester is one to two days to enjoy highlights like the Castle Fun Center, The Rock Sports Complex, and the Sugar Loaf Performing Arts Center. An extended stay of three to four days allows travelers to explore at a more relaxed pace and savor the local dining, including Italian, North American, and Asian cuisine.
What are the top things to do in and around Chester?
Chester offers a mix of family fun, outdoor activities, and cultural experiences for travelers:


How do I plan a trip to Chester?
To plan your trip to Chester, book flights and hotels in advance, especially during popular travel times. Consider a rental car for exploring. You can enjoy activities like Castle Fun Center, The Rock Sports Complex, and Sugar Loaf Performing Arts Center. Remember to pair outdoor plans with indoor backups for weather flexibility.
What cuisines can you find in Chester?
In Chester, you can find Mexican cuisine, with options like tacos, burritos, and enchiladas. Travelers can also enjoy Italian dishes such as pasta, North American fare including Southern soul food, and various Asian options like Chinese, Japanese, and Thai food. Mediterranean dishes are also available.
Can I book a refundable hotel in Chester?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Chester by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Chester with Expedia?
Expedia makes it easier to plan your Chester trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Chester?
The best choice depends on your travel style. Hotels in Chester can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Chester trip on Expedia?
Once you've booked your Chester trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Chester trip?
Expedia offers customer support before, during, and after your Chester trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Chester?
If it's your first trip to Chester, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Chester hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Chester hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Chester

An aerial view of a town with a river, industrial buildings, and a bridge.

Goshen

A historic castle by a calm river at night.

Warwick

A town with a main road, residential houses, and a baseball field.

Washingtonville

A snow-covered town with historic buildings and a church steeple.

Monroe

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