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
The price is AED 492 per night from May 26 to May 27
AED 492
AED 557 total
26 May - 27 May
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 ...
8.4/10 Very Good! (1,000 reviews)
"The stay was affordable, convenient, and the breakfast was good!"
Reviewed on 12 May 2025
HYATT house Fishkill/Poughkeepsie
100 Westage Business Center Dr., Fishkill, NY
The price is AED 403 per night from May 20 to May 21
AED 403
AED 456 total
20 May - 21 May
includes taxes & 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! (1,002 reviews)
"The free morning breakfast was better than most. However, the evening menu left a little to be desired. The staff was polite and accommodating and the room was a good value."
Reviewed on 13 May 2025
La Quinta Inn & Suites by Wyndham Middletown
551 Route 211 E, Middletown, NY
The price is AED 459 per night from May 26 to May 27
AED 459
AED 543 total
26 May - 27 May
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 helpful staff and the clean ...
9.2/10 Wonderful! (696 reviews)
"decent for the price. Friendly staff"
Reviewed on 15 May 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.
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
Stay at this vacation home in Fishkill. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions SplashDown Beach and Van Wyck Homestead Museum ...
9.6/10 Exceptional! (10 reviews)
Overnight
"Quiet clean property. Easy check in process and convenient to major highway"
Reviewed on 14 May 2025
Cozy Cabin with Sauna & Firepit!
Monroe
Stay at this vacation home in Monroe. Enjoy air conditioning. Popular attractions Woodbury Common Premium Outlets and Palaia Vineyards Winery are located ...
9.4/10 Exceptional! (24 reviews)
Charming Cabin
"We enjoyed our short stay at this comfy little cabin! It’s cozy and has a “lived-in” feel—definitely a bit worn, but still charming and functional. The outdoor space is the real highlight: the deck, fire pit, and sauna were perfect for relaxing. It’s also in a great location near wineries and some ..."
Reviewed on 1 May 2025
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View
Newburgh
Book a stay at this family-friendly vacation home in Newburgh. Enjoy free WiFi, a water park, and a fitness center. Our guests praise the helpful staff in our ...
10/10 Exceptional! (286 reviews)
Beautiful memory in orange lake
"This house is even better than the pictures and contains everything you need for a short trip around New York. My friends and I were in awe of the place and everything was just wonderful. We will be back again."
Reviewed on 15 May 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!
- 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
- World Headquarters of Jehovah's Witnesses
- United States Military Academy
- Mountain Creek Waterpark
- Mountain Creek Ski Resort
- Dia Beacon
- Minnewaska State Park
- SplashDown Beach
- Ramapo College of New Jersey
- Storm King Art Center
- Rockland County Courthouse
- Brotherhood Winery
- Hudson River
- Warwick Valley Winery and Distillery
- Angry Orchard
- Orange County Fair Speedway
- Harriman State Park
- Resorts World Hudson Valley
- Orange County Fairgrounds
- High Point State Park
- Rockland Community College
- Mount Saint Mary's College Newburgh
- Campgaw Mountain Ski Area
- Galleria at Crystal Run
- Paramount Hudson Valley Theater