Chester, NY
Travel Guide
Visit Chester
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
$112 nightly
The price is $138 total per night from May 11 to May 12
$138 total
May 11 - May 12
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 ...
8.6/10 Excellent! (1,005 reviews)
The hotel is very clean and well maintained. The staff is very friendly and helpful. The water pressure was low in the shower.
Reviewed on May 4, 2026
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
$119 nightly
The price is $141 total per night from May 31 to Jun 1
$141 total
May 31 - Jun 1
Total with taxes and 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! (1,019 reviews)
Bed was very comfortable and the breakfast was very good and provided a nice selection of food.
Reviewed on May 6, 2026
Spark by Hilton Fishkill
20 Schuyler Blvd Fishkill NY
$98 nightly
The price is $113 total per night from May 18 to May 19
$113 total
May 18 - May 19
Total with taxes and fees
Book a stay at this golf hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
8/10 Very Good! (81 reviews)
The staff were very accommodating and attentive to my requests of staying in a quieter floor with a later check-in. The room was extremely clean and bigger than I expected, with the AC working perfectly (as I like to sleep in a cold room). Breakfast was no-frills (bagels, cereal, juice, etc) but ...
Reviewed on Apr 30, 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! (135 reviews)
The mountain was wonderful!
Reviewed on Apr 13, 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
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.
Explore a world of travel with Expedia
- New York Hotels
- Hotels near Castle Fun Center
- Hotels near Museum Village
- Hotels near LEGOLAND® New York
- Hotels near The Rock Sports Complex
- Hotels near Goosepond Mountain State Park
- B&B in Sugar Loaf
- Sugar Loaf Hotels
- 5 Star Hotels in Sugar Loaf
- Rv Parks in Sugar Loaf
- Motels in Sugar Loaf
- Apartments in Sugar Loaf
- 4 Star Hotels in Sugar Loaf
- Cabin Rentals in Sugar Loaf
- Goshen Hotels
- Hotels near Goshen Historic Track
- Hotels near Harness Racing Museum and Hall of Fame
- Cabin Rentals in Goshen
- Hilton Hotels in Goshen
- B&B in Goshen
- Hotels with a Pool in Goshen
- Hotels with Hot Tubs in Goshen
- 4 Star Hotels in Goshen
- Apartments in Goshen
- Family Hotels in Goshen
- Hotels with Restaurants in Goshen
- Resorts in Goshen
- 5 Star Hotels in Goshen
- Pet-Friendly Hotels in Goshen
- Condo Rentals in Goshen
- Villas in Goshen
- Wyndham Hotels in Goshen
- Hotel Wedding Venues Hotels in Goshen
- Hotels with Connecting Rooms in Goshen
- Romantic Hotels in Goshen
- Luxury Hotels in Goshen
- Motels in Goshen
- Cottages in Goshen
- Hotels with an Outdoor Pool in Goshen
- Waterpark Hotels in Goshen
- 3 Star Hotels in Goshen
- Rv Parks in Goshen
- Resorts & Hotels with Spas in Goshen
- Winery Hotels in Goshen
- Non-Smoking Hotels in Goshen
- Hotels with Laundry Facilities in Goshen
- Hotels near Museum Village
- Walton Park Hotels
- Monroe Hotels
- 5 Star Hotels in Monroe
- Motels in Monroe
- Villas in Monroe
- B&B in Monroe
- Hotels with Hot Tubs in Monroe
- Romantic Hotels in Monroe
- Rv Parks in Monroe
- Florida Hotels
- Pet-Friendly Hotels in Monroe
- Beach Hotels in Monroe
- Hilton Hotels in Monroe
- Vacation Homes in Monroe
- Resorts in Monroe
- 4 Star Hotels in Monroe
- Hotels with Bars in Monroe
- Winery Hotels in Monroe
- Guest Houses in Monroe
- Car rentals near LEGOLAND® New York
- Car rentals near Sugar Loaf
- Car rentals near Goshen
- Thrifty Car Rental Rental Cars in Goshen
- Van Car Rentals in Goshen
- Enterprise Rental Cars in Goshen
- Budget Rental Cars in Goshen
- Luxury Car Rentals in Goshen
- Car rentals near Walton Park
- Car rentals near Monroe
- Budget Rental Cars in Monroe
- 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
- United States Military Academy
- Dia Beacon
- World Headquarters of Jehovah's Witnesses
- Mountain Creek Waterpark
- Minnewaska State Park
- Mountain Creek Ski Resort
- Delaware River
- Hudson River
- Angry Orchard
- Resorts World Hudson Valley
- SplashDown Beach
- Rockland County Courthouse
- Galleria at Crystal Run
- Storm King Art Center
- Orange County Fair Speedway
- Harriman State Park
- Paramount Hudson Valley Theater
- Warwick Valley Winery and Distillery
- Hudson Highlands State Park
- Rockland Lake State Park
- High Point State Park
- Algonquin Park
- Brotherhood Winery
- Mount Saint Mary's College Newburgh