4/5 - Good
Verified traveler
Nice, friendly town.
Chester, NY
Travel Guide
Visit Chester
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place, Chester, NY
The price is $122 per night from May 4 to May 5
$122
includes taxes & fees
$108 per night
May 4 - May 5
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 ...
8.4/10 Very Good! (1,000 reviews)
"I only stayed for the night but the front desk was nice and quick. Area is very quiet and peaceful."
Reviewed on Apr 11, 2025
Overlook Lodge at Bear Mountain
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
The price is $139 per night from May 14 to May 15
$139
includes taxes & fees
$122 per night
May 14 - May 15
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 ...
8.2/10 Very Good! (1,005 reviews)
"Very nice place."
Reviewed on Apr 26, 2025
La Quinta Inn & Suites by Wyndham Middletown
551 Route 211 E, Middletown, NY
The price is $150 per night from May 5 to May 6
$150
includes taxes & fees
$127 per night
May 5 - May 6
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (684 reviews)
Clean, friendly service, lots of parking
"Just an overnight stop but this place was perfect! It was quiet, clean, Elora at the front desk was lovely and it was reasonably priced."
Reviewed on Apr 28, 2025
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.
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
Stay at this vacation home in Fishkill. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions SplashDown Beach and Van Wyck Homestead Museum ...
9.6/10 Exceptional! (6 reviews)
Cozy and comfortable
"The house was beautiful, cozy, and very comfortable. We only stayed for one night, and since it was raining, we didn’t get a chance to explore the surrounding area. One cool feature was the projector and screen in the living room — it definitely made our trip more fun and memorable. The only minor ..."
Reviewed on Apr 13, 2025
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
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 ...
Beautiful views & quiet - would recommend
"We enjoyed our stay. The views are great and the space comfortable. It worked well for our visit with family living nearby and visiting Bear Mountain."
Reviewed on Apr 4, 2025
Cozy Cabin with Sauna & Firepit!
Monroe
Stay at this vacation home in Monroe. Enjoy air conditioning. Popular attractions Woodbury Common Premium Outlets and Palaia Vineyards Winery are located ...
9.4/10 Exceptional! (24 reviews)
Sweet Cabin to Enjoy with Family
"We stayed at this cozy cabin in Monroe for 4 days since we were looking for a somewhat close location to West Point to visit our cadet. This cabin had plenty of room for the three of us. The floor plan was open, which was nice. The beds are comfy, and there are several useful amenities of which to ..."
Reviewed on Mar 26, 2025
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.
Popular places to visit
The Rock Sports Complex
4/5(4 reviews)
Explore the great outdoors at The Rock Sports Complex, a lovely green space in Chester. While you're in the area, find time to visit its shops.
Castle Fun Center
4/5(7 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.
Museum Village
5/5(1 review)
You can spend an afternoon exploring the galleries in Museum Village during your trip to Chester. While in this family-friendly area, find time to visit its shops.
Reviews of Chester
4.2
Top Destination
5/5 - Excellent
Rosalie
I also visited Franklin D. Roosevelt's Hyde Park home, Library, & Museum.We went to the Mower Flea Market in Woodstock, NY. We also went to the Ulster County Fair.We were disappointed that the Culinary Arts Institute Restaurants were closed.
5/5 - Excellent
Verified traveler
Advise caution; Kathy's scones are seriously addictive. The Chester-Blooming Grove-Washingtonville and larger area has a sufficient number of interesting restaurants. This is a peaceful location to stay for day trips to Hudson Valley attractions.
5/5 - Excellent
Verified traveler
Tina's pizza was great
3/5 - Okay
Verified traveler
Lots of fast food and gas stations. One bright spot the Chester Dinner has good food band an extensive gluten free menu.
4/5 - Good
Verified traveler
make a trip to Bellville dairy for their ice cream!
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Packages
- Galleria at Crystal Run
- Mount Saint Mary's College Newburgh
- Brotherhood Winery
- Dia Beacon
- LEGOLAND® New York
- Ramapo College of New Jersey
- Angry Orchard
- World Headquarters of Jehovah's Witnesses
- Storm King Art Center
- Castle Fun Center
- Rockland Community College
- Orange County Fair Speedway
- Museum Village
- United States Military Academy
- Mountain Creek Waterpark
- Bear Mountain State Park
- The Rock Sports Complex
- Campgaw Mountain Ski Area
- Woodbury Common Premium Outlets
- Goosepond Mountain State Park
- Harriman State Park
- Minnewaska State Park
- Hudson River
- High Point State Park
- Mountain Creek Ski Resort
- Mount Peter Ski Area
- Michie Stadium
- SplashDown Beach
- Crystal Springs Golf Resort
- Warwick Valley Winery and Distillery
- Rockland County Courthouse
- The Rock Sports Complex
- Castle Fun Center
- Museum Village
- Goosepond Mountain State Park
- LEGOLAND® New York
- Woodbury Common Premium Outlets
- Crystal Springs Golf Resort
- Bear Mountain State Park
- World Headquarters of Jehovah's Witnesses
- United States Military Academy
- Mountain Creek Waterpark
- Mountain Creek Ski Resort
- Dia Beacon
- Minnewaska State Park
- SplashDown Beach
- Ramapo College of New Jersey
- Storm King Art Center
- Rockland County Courthouse
- Brotherhood Winery
- Hudson River
- Warwick Valley Winery and Distillery
- Angry Orchard
- Orange County Fair Speedway
- Harriman State Park
- Resorts World Hudson Valley
- Orange County Fairgrounds
- High Point State Park
- Rockland Community College
- Mount Saint Mary's College Newburgh
- Campgaw Mountain Ski Area
- Galleria at Crystal Run
- Paramount Hudson Valley Theater