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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, (1,002 reviews)
"Nice room breakfast was ok needs to be hot not judt luke warm."
United States
Donna
The price is ₩146,834
₩173,447 total
includes taxes & fees
Mar 22 - Mar 23
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 ₩322,137
₩364,419 total
includes taxes & fees
Mar 19 - Mar 20
The Dominion House Bed & Breakfast

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (611 reviews)
"Clean spacious room, friendly staff."
United States
Dennis
The price is ₩148,333
₩167,616 total
includes taxes & fees
Mar 18 - Mar 19
Days Inn by Wyndham Wurtsboro

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (155 reviews)
"Our room was beautiful and well maintained and spotlessly clean. I did not realize before we came to the hotel that the bathroom was out in the hall, not en suite. "
United States
Andrea
The price is ₩138,009
₩160,799 total
includes taxes & fees
Mar 19 - Mar 20
Borland House Inn

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
7.8 out of 10, Good, (17 reviews)
"The cleaning could have been better"
United States
Yuna
The price is ₩146,984
₩180,976 total
includes taxes & fees
Mar 22 - Mar 23
Comfort Suites Central Valley - Woodbury

High Point Motel

High Point Motel
2.0 star property
Sussex
9.2 out of 10, Wonderful, (116 reviews)
"They are always great! Our spot away from home "
United States
CANDICE
The price is ₩118,666
₩132,465 total
includes taxes & fees
Mar 17 - Mar 18
High Point Motel

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1,004 reviews)
"Great stay!!! "
United States
diana
The price is ₩138,818
₩163,979 total
includes taxes & fees
Mar 22 - Mar 23
Courtyard by Marriott Middletown Goshen

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very Good, (1,004 reviews)
"Superb place to stay."
United States
Denessy
The price is ₩133,484
₩150,984 total
includes taxes & fees
Mar 30 - Mar 31
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,006 reviews)
"Great staff and clean rooms. Beautiful views."
United States
Renee
The price is ₩178,299
₩201,703 total
includes taxes & fees
Mar 17 - Mar 18
Overlook Lodge at Bear Mountain

The Hamlet Inn at Warwick

The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (154 reviews)
"good accommodations "
United States
Alejandro
The price is ₩127,356
₩144,077 total
includes taxes & fees
Mar 17 - Mar 18
The Hamlet Inn at Warwick

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG
2.5 star property
Montgomery
8.8 out of 10, Excellent, (832 reviews)
"clean, warm room. "
United States
Michael
The price is ₩146,834
₩166,105 total
includes taxes & fees
Mar 22 - Mar 23
Holiday Inn Express & Suites Montgomery by IHG

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
7.6 out of 10, Good, (40 reviews)
"The place was spotless and the staff were very friendly. The bed was so comfortable lovely stay "
United States
sharon
The price is ₩140,092
₩161,982 total
includes taxes & fees
Mar 24 - Mar 25
Spark by Hilton Fishkill

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (1,002 reviews)
"A lot to do over there, good for a whole weekend, or even more. Had great time. "
United States
illay
The price is ₩129,319
₩148,232 total
includes taxes & fees
Mar 29 - Mar 30
Quality Inn near Mountain Creek

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,006 reviews)
"Best Hotel in area so far 😁 "
United States
Debi
The price is ₩150,970
₩178,332 total
includes taxes & fees
Mar 24 - Mar 25
Sleep Inn & Suites Middletown - Goshen

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
8.8 out of 10, Excellent, (1,003 reviews)
"Amazing staff Great breakfast Clean quiet rooms"
United States
R
The price is ₩157,922
₩194,440 total
includes taxes & fees
Mar 22 - Mar 23
Fairfield Inn & Suites by Marriott Goshen Middletown

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,002 reviews)
"Room clean, staff friendly"
United States
KATHRYN
The price is ₩134,998
₩159,467 total
includes taxes & fees
Mar 23 - Mar 24
Hampton Inn by Hilton Middletown

Rolling Hills Motel

Rolling Hills Motel
2.0 star property
Sussex
8.6 out of 10, Excellent, (205 reviews)
"Great local spot. Recently updated "
United States
Steve
The price is ₩116,868
₩130,458 total
includes taxes & fees
Mar 29 - Mar 30
Rolling Hills Motel

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (1,004 reviews)
"Wonderful accommodations!!"
United States
Roxanne
The price is ₩170,777
₩201,732 total
includes taxes & fees
Mar 22 - Mar 23
Hampton Inn & Suites Newburgh Stewart Airport

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is ₩247,221
₩461,105 total
includes taxes & fees
Mar 31 - Apr 1
Hike & Fish: Outdoor Retreat Near Trails

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (985 reviews)
"Best hotel in town. Clean clean smoke free hotel "
United States
David
The price is ₩174,478
₩206,103 total
includes taxes & fees
Mar 22 - Mar 23
La Quinta Inn & Suites by Wyndham Middletown-Goshen
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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 DoubleTree by Hilton Hotel Nanuet and Sonesta Simply Suites Nanuet. See all available top hotels, or 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 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 19 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.