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Our top choices for Chester hotels

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.6 out of 10, Excellent, (1,000 reviews)
"Very clean, good breakfast. Well lit. Packed a few amenities, but good for the price."
United States
Shanen
The price is ¥18,597
¥22,899 total
includes taxes & fees
May 17 - May 18
Holiday Inn Express Hotel & Suites Chester by IHG

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233 reviews)
"Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY."
United States
Erek
The price is ¥33,796
¥38,232 total
includes taxes & fees
Jun 1 - Jun 2
The Dominion House Bed & Breakfast

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,068 reviews)
"Clean room, polite and friendly staff, and nice location. "
United States
Cheryl
The price is ¥19,049
¥21,549 total
includes taxes & fees
May 27 - May 28
Sleep Inn & Suites Monroe - Woodbury

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,107 reviews)
"Clean room, friendly staff, good breakfast!"
United States
Sarah
The price is ¥23,054
¥28,386 total
includes taxes & fees
May 28 - May 29
Hampton Inn Harriman Woodbury

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84
2.5 star property
Fishkill
9.0 out of 10, Wonderful, (1,001 reviews)
"Great hotel for the price!"
United States
Jacqueline
The price is ¥15,994
¥18,493 total
includes taxes & fees
Jun 7 - Jun 8
Quality Inn & Suites Fishkill South near I-84

High Point Motel

High Point Motel
2.0 star property
Sussex
9.2 out of 10, Wonderful, (135 reviews)
"Nice, clean motel. Chairs outside to enjoy the mountain view. Would definitely stay here again if in the area."
United States
Gregory
The price is ¥13,833
¥15,441 total
includes taxes & fees
May 31 - Jun 1
High Point Motel

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh
3.0 star property
Newburgh
7.0 out of 10, Good, (751 reviews)
"Easy parking and clean room. The staff were polite and friendly. "
United States
Sarah
The price is ¥14,006
¥16,544 total
includes taxes & fees
May 17 - May 18
The Crossroads Hotel, Newburgh

Holiday Inn Express Haskell - Wayne Area by IHG

Holiday Inn Express Haskell - Wayne Area by IHG
2.5 star property
Wanaque
9.0 out of 10, Wonderful, (1,004 reviews)
"Clean and awesome hotel! We will be back next time we’re in the area"
United States
karine
The price is ¥20,592
¥23,604 total
includes taxes & fees
May 25 - May 26
Holiday Inn Express Haskell - Wayne Area by IHG

Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah
2.5 star property
Mahwah
8.8 out of 10, Excellent, (1,492 reviews)
"Lovely breakfast was included. The parking was plentiful & safe"
United States
Teresa
The price is ¥17,254
¥19,778 total
includes taxes & fees
May 17 - May 18
Hampton Inn & Suites Mahwah

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
9.0 out of 10, Wonderful, (1,000 reviews)
"Staff was wonderful , very clean hotel"
United States
Edna
The price is ¥21,906
¥26,972 total
includes taxes & fees
May 25 - May 26
Fairfield Inn & Suites by Marriott Goshen Middletown

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG
3.5 star property
Suffern
8.8 out of 10, Excellent, (1,008 reviews)
"I liked the bar drinks and breakfast was good"
United States
Leslie
The price is ¥18,597
¥21,643 total
includes taxes & fees
May 25 - May 26
Crowne Plaza Suffern - Mahwah by IHG

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.0 out of 10, Wonderful, (1,009 reviews)
"Rooms were so big and very clean the beds were excellent loved the big bathroom "
United States
ROMAN
The price is ¥16,950
¥19,597 total
includes taxes & fees
May 25 - May 26
Comfort Suites Fishkill near Interstate 84

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,006 reviews)
"Great breakfast, clean rooms "
United States
KASEY
The price is ¥19,314
¥22,816 total
includes taxes & fees
Jun 9 - Jun 10
Sleep Inn & Suites Middletown - Goshen

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very Good, (1,010 reviews)
"Breakfast is over at 10am, the pool is open in the evening very small but overall good for kids. Great stay and price."
United States
Stacey
The price is ¥18,620
¥21,992 total
includes taxes & fees
Jun 8 - Jun 9
Courtyard by Marriott Middletown Goshen

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (1,000 reviews)
"Large shower, clean, good breakfast, right off the highway, convenient parking "
United States
Michelle
The price is ¥20,494
¥24,210 total
includes taxes & fees
May 28 - May 29
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,008 reviews)
"Breakfast was great and hotel was clean"
United States
Brigitte
The price is ¥16,504
¥19,495 total
includes taxes & fees
May 26 - May 27
Hampton Inn by Hilton Middletown

SpringHill Suites by Marriott Fishkill

SpringHill Suites by Marriott Fishkill
3.0 star property
Fishkill
9.6 out of 10, Exceptional, (1,000 reviews)
"The place is great! The room was very nice. But the breakfast buffet leaves a lot to be desired! It was very basic, nothing different from any other hotel."
United States
Sunil
The price is ¥23,421
¥27,082 total
includes taxes & fees
Jun 7 - Jun 8
SpringHill Suites by Marriott Fishkill

Holiday Inn Express Ramsey-Mahwah by IHG

Holiday Inn Express Ramsey-Mahwah by IHG
2.5 star property
Ramsey
9.2 out of 10, Wonderful, (1,012 reviews)
"Very good place to stay. Excellent breakfast, great beds/pillows, location, staff. Two thumbs up!"
United States
Robert
The price is ¥18,439
¥21,136 total
includes taxes & fees
May 24 - May 25
Holiday Inn Express Ramsey-Mahwah by IHG

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport
3.0 star property
Newburgh
8.0 out of 10, Very Good, (756 reviews)
"Staff was professional and attentive to our requests throughout the stay. Patti at the front desk was delightful to interact with."
United States
Ignacio
The price is ¥18,548
¥21,908 total
includes taxes & fees
May 31 - Jun 1
Courtyard by Marriott Newburgh Stewart Airport

Garner Hotel Mahwah by IHG

Garner Hotel Mahwah by IHG
2.5 star property
Mahwah
9.0 out of 10, Wonderful, (449 reviews)
"The staff was very nice. Very easy to get to. Breakfast was fine and parking was nice to have. "
United States
Elizabeth
The price is ¥18,912
¥21,679 total
includes taxes & fees
May 17 - May 18
Garner Hotel Mahwah by IHG
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Stay near popular Chester attractions

Learn more about Chester

Lace up your hiking boots and hit the trails at Goosepond Mountain State Park for stunning views. After working up an appetite, head to Castle Fun Center for go-karts, mini-golf, and arcade games.

Black dirt region farm Chester New York

Top Chester Hotel Reviews

More cheap stays in Chester

Frequently asked questions

What's the best place to stay in Chester?
Based on our traveler data, Holiday Inn Express Hotel & Suites Chester by IHG is one of the top choices for your stay. This hotel offers free breakfast and an indoor pool. Other good options for your trip to the area are Sleep Inn & Suites Middletown - Goshen and Overlook Lodge at Bear Mountain. See all available top hotels, or vacation rentals in Chester.
What's the top vacation rental in Chester?
Perfect and Spacious Hudson Valley Escape!: Visitors like this Chester vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. See all vacation rentals in Chester.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes, you'll find most hotel bookings are refundable if you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, you might be able to still cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
Where can I learn more about changing or cancelling my trip to Chester?
For more details about updating your trip to Chester or cancelling it, click here.
What's the best place to stay for families in Chester?
The Dominion House Bed & Breakfast is a B&B with an outdoor pool and free parking, and it's a top choice on Expedia for families. Kids of all ages will also enjoy a visit to Castle Fun Center. Find more child-friendly accommodations in Chester.
What is the favorite LGBTQ-friendly place to stay in Chester?
Holiday Inn Express Hotel & Suites Chester by IHG is a top LGBTQ-friendly hotel that features free breakfast and free WiFi. The Dominion House Bed & Breakfast is another good option for your trip. See all available hotels listed as LGBTQ-friendly in Chester.
Where is the best hotel to stay with easy access to The Rock Sports Complex?
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and an indoor pool. It's located just a short 0.8 mi (1.3 km) from The Rock Sports Complex. Other good options within 5 miles include Fairfield Inn & Suites by Marriott Goshen Middletown and NATURE'S NIRVANA FOR FAMILY AND FRIEND.
What about the best place to stay near Castle Fun Center?
One of the top choices for your stay is Holiday Inn Express Hotel & Suites Chester, an IHG Hotel, located a short 0.4 mi (0.6 km) from Castle Fun Center, and this hotel offers free breakfast and an indoor pool. Fairfield Inn & Suites by Marriott Goshen Middletown and Stagecoach Inn are two other good options within a few miles.
What are some accommodations with pools in Chester?
Holiday Inn Express Hotel & Suites Chester by IHG is a top hotel with a pool, free on-the-go breakfast, and free WiFi. View all hotels with pools in Chester.
What is the best hotel near Stewart International Airport (SWF)?
Howard Johnson by Wyndham Newburgh is a popular hotel, featuring free breakfast and free WiFi. It's located a short 0.8 mi (1.2 km) from Stewart Intl. Airport. Other options within close proximity to the airport include Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport and Super 8 by Wyndham Newburgh/West Point Near Stewart Airport.
What is staying in Chester like?
Visitors to Chester are sure to enjoy the shopping and restaurants. Tourists can also enjoy the city's ski areas and coffeehouses. In Chester, there are 18 hotels and other accommodations to choose from. Find out more about Chester.
What are the top places to visit in Chester?
Favorite places to visit include Castle Fun Center, The Rock Sports Complex, and Museum Village. Additionally, you might want to add Goosepond Mountain State Park to your itinerary. Check out what more to see and do in Expedia's Chester guide.
What's the seasonal weather like in Chester?
The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Chester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.

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