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
The price is $134 total per night from Sep 8 to Sep 9
$134 total
per night
Sep 8 - Sep 9
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 ...
8.6/10 Excellent! (1,009 reviews)
"The staff was not attentive to my concerns throughout my stay. I repeatedly asked for towels and was told that there were none available. I also requested that my room be cleaned, and although I was told it would be taken care of, no one ever came to clean the room. The breakfast experience was also ..."

Reviewed on Sep 6, 2026

Holiday Inn Express Hotel & Suites Chester by IHG
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
The price is $131 total per night from Oct 7 to Oct 8
$131 total
per night
Oct 7 - Oct 8
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
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
The price is $142 total per night from Oct 1 to Oct 2
$142 total
per night
Oct 1 - Oct 2
Book a stay at this business-friendly hotel in Suffern. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,042 reviews)
"Their restaurant has no service ! I waited so long to get a water and they never brought anything , I told the front desk and they did not care either… I asked them to bring coffee capsules to the room they told me to go get it myself ! It’s not the cleanest hotel ! It’s old and water was dripping ..."

Reviewed on Sep 4, 2026

Crowne Plaza Suffern - Mahwah by IHG
See all 1,039 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 ...
8/10 Very Good! (1 review)
"Host was very nice and accommodating. The house was clean and comfortable. There is a beautiful tub in the master bath but I was wishing there was a shower there. Master bed was very comfortable but also very tall for a shorter person like myself. Overall very nice."

Reviewed on Aug 19, 2026

Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8
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 ...
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Warwick NY
Stay at this vacation home in Warwick. Enjoy air conditioning. Popular attractions Railroad Green and Strazza Art Gallery are located nearby.
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
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.
See properties

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

Explore a world of travel with Expedia