Chester, NY
Travel Guide
Visit Chester
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
The price is ￥18,488 per night from May 17 to May 18
￥18,488
￥22,764 total
May 17 - May 18
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! (1,010 reviews)
Deanna, the staffperson at the front desk when we arrived, and later in the evening, was a delight. Upbeat, polite, attentive and helpful! The next day, when we were checking out, the fellow at the front desk, who said he was the manager, had no idea how to direct us to route 17. He said he was new ...
Reviewed on May 11, 2026
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
The price is ￥19,967 per night from Jun 9 to Jun 10
￥19,967
￥23,586 total
Jun 9 - Jun 10
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 ...
8.8/10 Excellent! (1,025 reviews)
Yea but the room next to us had music blasting all night
Reviewed on May 11, 2026
Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
The price is ￥18,857 per night from May 12 to May 13
￥18,857
￥23,217 total
May 12 - May 13
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! (1,011 reviews)
The hotel is a bit dated to some but that’s what keeps the city rif raff away. Hikers and outdoor enthusiasts stay here so be prepared to use the grounds and stay outside most of the time. When you finally do crash inside you will find very comfortable beds, amazing views and complimentary water. ...
Reviewed on May 10, 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.
Elegant Home w/7BRs, Game Room, Luxury Yard, Pool
Chester NY
Stay at this vacation home in Chester. Enjoy laundry facilities and air conditioning. Popular attractions LEGOLAND® New York and Castle Fun Center are located ...
9/10 Wonderful! (2 reviews)
Good location near Harriman State Park, Legoland, Sugar Loaf. Easy access from Newark airport. House is nice but needs some minor maintenance in a bunch of different areas. Didn’t significantly impact stay. Pool area looked nice but was closed during our stay.
Reviewed on Oct 19, 2025
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 ...
9.8/10 Exceptional! (137 reviews)
My husband and I had a wonderful overnight stay here! Got in late on a chilly, rainy night and this was the most welcoming, cozy place to walk into. So thoughtfully decorated, with all the comforts of home. And the view! Felt like we were on top of the world in our own little piece of Heaven. Highly ...
Reviewed on Apr 26, 2026
Spacious 7BR Villa on 14 Acres w/ Indoor Pool
Washingtonville NY
Stay at this vacation home in Blooming Grove. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Brotherhood Winery and Palaia ...
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
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
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
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.
- LEGOLAND® New York
- Woodbury Common Premium Outlets
- Crystal Springs Golf Resort
- United States Military Academy
- Dia Beacon
- World Headquarters of Jehovah's Witnesses
- Minnewaska State Park
- Rockland County Courthouse
- Harriman State Park
- Warwick Valley Winery and Distillery
- Hudson Highlands State Park
- West Point Museum
