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
$114 nightly
The price is $140 total per night from Nov 22 to Nov 23
$140 total
Nov 22 - Nov 23
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
$104 nightly
The price is $122 total per night from Nov 2 to Nov 3
$122 total
Nov 2 - Nov 3
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 ...
Overlook Lodge at Bear Mountain
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
$127 nightly
The price is $148 total per night from Nov 2 to Nov 3
$148 total
Nov 2 - Nov 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Suffern. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
Crowne Plaza Suffern - Mahwah by IHG
See all 1,064 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.
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 ...
7.8/10 Good! (26 reviews)
"The property was clean and pet friendly. However, the small extended stay room with a kitchen had no glasses or bowls or flat ware. You can't expect any additional accomodations beyond the room."

Reviewed on Oct 12, 2026

1 Queen Bed | Non-Smoking, Kitchen
TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE

Pine Bush NY
Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Ellenville Fault Ice Caves and VerKeerderkill Falls are located nearby.
10/10 Exceptional! (25 reviews)
"We loved our stay. The property and pictures are exactly as posted very quiet, peaceful space, exactly what we were looking for. Took our dog as well Our hosts were wonderful and responded to any questions we had. Definitely recommend. We stayed 2 nights to explore Lake Minnewaska, great location….RV ..."

Reviewed on Oct 23, 2026

TRANQUIL MOUNTAIN SOLITUDE
Luxe 10 guest Cabin/Skiing/Pools/Tennis/Gym/Hiking

Luxe 10 guest Cabin/Skiing/Pools/Tennis/Gym/Hiking

vernon NJ
Book a stay at this golf cabin in Vernon. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Mountain Creek Ski Resort and Crystal ...
9.2/10 Wonderful! (35 reviews)
"The property was very clean, well appointed and as advertised. The owner was a pleasure to deal with- he provided excellent detailed information and was incredibly responsive to all our questions. It was a great stay."

Reviewed on Oct 7, 2026

Luxe 10 guest Cabin/Skiing/Pools/Tennis/Gym/Hiking
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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