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Our top choices for Chester hotels

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
West Springfield
7.8 out of 10, Good, (119 reviews)
"Clean room and very spacious, staff was friendly, i would only add a small dinning table to the room. "
United States
Tomarie
The price is ₩124,294
₩142,254 total
includes taxes & fees
Mar 3 - Mar 4
Baldwin Inn & Suites, SureStay Collection by Best Western

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,000 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is ₩136,811
₩152,817 total
includes taxes & fees
Mar 2 - Mar 3
Best Western Plus Berkshire Hills Inn & Suites

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (20 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is ₩198,111
₩221,289 total
includes taxes & fees
Mar 10 - Mar 11
Element Lenox Berkshires

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,000 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is ₩123,566
₩138,023 total
includes taxes & fees
Mar 26 - Mar 27
Quality Inn Lee - Lenox South

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (824 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,240 reviews)
"Great service, clean & quiet rooms, and a solid breakfast to start the day"
United States
Stephanie
D. Hotel Suites & Spa

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very Good, (114 reviews)
"Friendly staff, really nice room, quiet. I really enjoyed my stay."
United States
Desiree
The price is ₩141,101
₩157,610 total
includes taxes & fees
Mar 1 - Mar 2
River Valley Inn

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (572 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is ₩106,895
₩119,409 total
includes taxes & fees
Mar 2 - Mar 3
Travelodge by Wyndham Great Barrington Berkshires

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (740 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is ₩147,087
₩164,296 total
includes taxes & fees
Mar 1 - Mar 2
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (614 reviews)
"Room was spotless, staff were nice. "
United States
Jose I Medina
The price is ₩168,181
₩187,858 total
includes taxes & fees
Mar 22 - Mar 23
Fairfield Inn & Suites Springfield Holyoke

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (974 reviews)
"clean room, nice staff"
United States
david
The price is ₩163,905
₩183,082 total
includes taxes & fees
Mar 9 - Mar 10
The Ellery

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is ₩83,378
₩91,465 total
includes taxes & fees
Mar 10 - Mar 11
Pleasant Valley Motel West Stockbridge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (864 reviews)
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
United States
Melissa
Berkshires Untold

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,000 reviews)
"Clean room, nice staff , decent breakfast. Overall a good stay . "
United States
Anindita
The price is ₩139,319
₩155,620 total
includes taxes & fees
Mar 19 - Mar 20
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (829 reviews)
"I will stay again"
United States
Jailene
The price is ₩163,620
₩182,763 total
includes taxes & fees
Mar 22 - Mar 23
Hampton Inn Westfield

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (427 reviews)
"Artful and inspiring interior decorating and delicious French toast for breakfast!"
United States
Marielle
The price is ₩144,647
₩164,110 total
includes taxes & fees
Mar 15 - Mar 16
Naomi's Inn Bed & Breakfast

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,001 reviews)
"Friendly clean accommodation were just what we needed. "
United States
Carrie
The price is ₩150,764
₩171,042 total
includes taxes & fees
Mar 9 - Mar 10
Tru by Hilton Chicopee Springfield

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very Good, (1,000 reviews)
"Very good place to stay"
United States
Gloria
The price is ₩139,749
₩159,943 total
includes taxes & fees
Mar 1 - Mar 2
Hampton Inn West Springfield

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (84 reviews)
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is ₩189,044
₩211,163 total
includes taxes & fees
Mar 1 - Mar 2
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (844 reviews)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is ₩128,259
₩143,267 total
includes taxes & fees
Mar 2 - Mar 3
Berkshire Inn
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.
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Stay near popular Chester attractions

Learn more about Chester

Experience the hiking, camping, and waterfalls in Chester!

An amazing keystone arch bridge!
Photo by Chris Addams
Open Photo by Chris Addams

Top Chester Hotel Reviews

More cheap stays in Chester

Frequently asked questions

What's the best place to stay in Chester?
D. Hotel Suites & Spa, located 19.1 mi (30.7 km) from the heart of Chester, is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are Berkshire Mountain Lodge and The Yankee, Trademark Collection by Wyndham. 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! Most hotel bookings are fully refundable as long as you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, it may still be possible to cancel it and get a refund within a 24-hour period of your 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 additional details about picking new dates or cancelling your trip to Chester, go to https://www.expedia.com/service/.
What's the best accommodation near Logan International Airport (BOS)?
Hilton Boston Logan Airport is a popular 4-star hotel featuring a restaurant and an indoor pool. It's located a short 0.2 mi (0.4 km) from Logan Intl. Airport. Other accommodations close to the airport are Hyatt Regency Boston Harbor and Embassy Suites Boston Logan Airport.
What is staying in Chester like?
Visitors can enjoy all that Chester has to offer including the waterfalls, shopping, and riverfront. Tourists can also enjoy the city's restaurants, theaters, and monuments. In Chester, there are 3 hotels and other accommodations to choose from. Find out more about Chester.
What should I see while I'm in Chester?
A favorite place to visit is Chester Town Hall. You'll also find Littleville Lake and Pyramid Lake in the area. 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 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.

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