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Featured Chester Family Hotels
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Fully refundable
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 ...
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.
Hotels with Pools in Chester
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
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! (1,005 reviews)
Yankee the hotel manager was great. Elevator was out of order but it was still amazing. She was so lovely and accommodating. The place was under construction but rooms were clean and spacious and pool and gym were nice
Reviewed on Jan 1, 2026
The Dominion House Bed & Breakfast
28 Old Dominion Road Chester NY
Stay at this B&B in Chester. Enjoy free breakfast, free parking, and a garden. Popular attractions LEGOLAND® New York and Brotherhood Winery are located ...
9.8/10 Exceptional! (89 reviews)
Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY.
Reviewed on Oct 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.
Hotels With Connecting Rooms in Chester
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
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 ...
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.
Hotels by Star Rating
More Hotel Options
- Hotels with a Pool in Chester
- Resorts & Hotels with Spas in Chester
- Hotels with Hot Tubs in Chester
- Hotels with Free Parking in Chester
- Winery Hotels in Chester
- Hotel Wedding Venues in Chester
- Romantic Hotels in Chester
- Hotels with smoking rooms in Chester
- Hotels with an Indoor Pool in Chester
- Pet-friendly Hotels in Chester
Top Points of Interests in Chester
- Hotels near Castle Fun Center
- Hotels near The Rock Sports Complex
- Hotels near Goosepond Mountain State Park
- Hotels near Museum Village
- Hotels near Woodbury Common Premium Outlets
- Hotels near LEGOLAND® New York
- Hotels near Mountain Creek Ski Resort
- Hotels near Crystal Springs Golf Resort
- Hotels near United States Military Academy
- Hotels near Bear Mountain State Park
- Hotels near Mount Peter Ski Area
- Hotels near Dia Beacon
- Hotels near Mountain Creek Waterpark
- Hotels near Campgaw Mountain Ski Area
- Hotels near World Headquarters of Jehovah's Witnesses
- Hotels near Minnewaska State Park
- Hotels near Rockland County Courthouse
- Hotels near Hudson River
- Hotels near Angry Orchard
- Hotels near Galleria at Crystal Run
Cities near Chester
- Pocono Mountains Hotels (60.91 mi)
- Wayne Hotels (29.65 mi)
- Upstate New York Hotels (136.16 mi)
- The Catskills Hotels (47.89 mi)
- Middletown Hotels (9.74 mi)
- Vernon Hotels (15.77 mi)
- Newburgh Hotels (16.67 mi)
- Suffern Hotels (18.24 mi)
- Fishkill Hotels (22.67 mi)
- Beacon Hotels (18.45 mi)
- Mahwah Hotels (20.05 mi)
- Hudson Valley Hotels (28.53 mi)
- New Paltz Hotels (28.24 mi)
- Ringwood Hotels (17.26 mi)
- Nanuet Hotels (22.59 mi)
- Peekskill Hotels (19.14 mi)
- Gardiner Hotels (22.78 mi)
- Warwick Hotels (8.62 mi)
- Goshen Hotels (3.87 mi)
- Bear Mountain Hotels (14.85 mi)