Chester, NY
Travel Guide
Visit Chester
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
The price is ￥18,402 per night from Sep 27 to Sep 28
￥18,402
￥22,656 total
Sep 27 - Sep 28
includes taxes & 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 ...
8.6/10 Excellent! (1,004 reviews)
"Was definitely worth the price. Much more than I expected for this area. Friendly staff, clean rooms, convenient location and very comfortable."
Reviewed on Sep 25, 2026
Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
The price is ￥15,610 per night from Sep 30 to Oct 1
￥15,610
￥19,219 total
Sep 30 - Oct 1
includes taxes & 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! (1,006 reviews)
"Great place to stay, especially with your dog. Trails everywhere great staff."
Reviewed on Sep 26, 2026
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
The price is ￥17,320 per night from Oct 19 to Oct 20
￥17,320
￥20,458 total
Oct 19 - Oct 20
includes taxes & 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 ...
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
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
Elegant Home w/7BRs, Game Room, Luxury Yard, Pool
Chester NY
Stay at this vacation home in Chester. Enjoy a garden, laundry facilities, and patios. Popular attractions LEGOLAND® New York and Castle Fun Center are located ...
8.8/10 Excellent! (3 reviews)
"Some thing good and some things not so good"
Reviewed on Jun 5, 2026
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 Blodgett Memorial Library and Van ...
8.6/10 Excellent! (21 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
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
- Woodbury Common Premium Outlets
- LEGOLAND® New York
- Crystal Springs Golf Resort
- United States Military Academy
- World Headquarters of Jehovah's Witnesses
- Minnewaska State Park
- Dia Beacon
- Warwick Valley Winery and Distillery
- Mount Peter Ski Area
- Harriman State Park
- West Point Museum
- Rockland County Courthouse
