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
$129 nightly
The price is $152 total per night from Jun 26 to Jun 27
$152 total
Jun 26 - Jun 27
Total includes 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 ...
8.4/10 Very Good! (1,007 reviews)
"Breakfast was great, a lot of options for all. The pool kept kids entertained. The door to our room was a bit wonky but everything was clean."
Reviewed on Jun 21, 2025
HYATT house Fishkill/Poughkeepsie
100 Westage Business Center Dr., Fishkill, NY
$111 nightly
The price is $126 total per night from Jul 1 to Jul 2
$126 total
Jul 1 - Jul 2
Total includes taxes and fees
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,003 reviews)
"Very nice, updated, clean and price was great. Pool and hot tub were also great."
Reviewed on Jun 18, 2025
Best Western The Inn At Ramsey
1315 Route 17 South, Ramsey, NJ
$93 nightly
The price is $107 total per night from Jul 7 to Jul 8
$107 total
Jul 7 - Jul 8
Total includes taxes and fees
Stay at this 3-star business-friendly hotel in Ramsey. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7.2/10 Good! (1,003 reviews)
"N/A"
Reviewed on Jun 14, 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.
Charming 1-bedroom Rekindled Farmhouse Historic Sugar Loaf, NY
Chester
Stay at this vacation home in Chester. Enjoy air conditioning. Popular attractions LEGOLAND® New York and The Rock Sports Complex are located nearby.
"Beautiful old farm house that has been very tastefully remodeled to keep its original charm. Host had house stocked with all the essentials incase you would have forgotten something. He knew we would be checking in late so offered to have the couch pulled out and made into a bed for our children ..."
Reviewed on Jun 15, 2025
Private Estate 9BR w/Pool, Hot Tub & Scenic Views!
Chester
Book a stay at this family-friendly villa in Chester. Enjoy free WiFi, private pools, and a garden. Popular attractions LEGOLAND® New York and Woodbury Common ...
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 ...
9.8/10 Exceptional! (93 reviews)
Anniversary weekend
"The property was perfect for our weekend! Truly truly a beautiful view!"
Reviewed on Jun 1, 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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- The Rock Sports Complex
- Castle Fun Center
- Museum Village
- Goosepond Mountain State Park
- LEGOLAND® New York
- Woodbury Common Premium Outlets
- Crystal Springs Golf Resort
- World Headquarters of Jehovah's Witnesses
- Bear Mountain State Park
- Mountain Creek Waterpark
- United States Military Academy
- SplashDown Beach
- Minnewaska State Park
- Mountain Creek Ski Resort
- Dia Beacon
- Hudson River
- Storm King Art Center
- Angry Orchard
- Rockland County Courthouse
- Orange County Fair Speedway
- Warwick Valley Winery and Distillery
- Brotherhood Winery
- Harriman State Park
- High Point State Park
- Resorts World Hudson Valley
- Campgaw Mountain Ski Area
- Ramapo College of New Jersey
- Michie Stadium
- Mount Saint Mary's College Newburgh
- Rockland Community College
- Hudson Highlands State Park
- Rockland Lake State Park