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Find hotels in Chester, MA from ￥10,913

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Dec 6 - Dec 7
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Compare 840 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Lobby sitting area
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, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is ￥14,520
￥16,219 total
includes taxes & fees
Dec 9 - Dec 10
Best Western Plus Berkshire Hills Inn & Suites
Exterior
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, (703)
"We stay here every year and it never disappoints "
United States
Elizabeth
The price is ￥16,599
￥18,541 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay!"
United States
Ann
The price is ￥13,863
￥15,485 total
includes taxes & fees
Dec 14 - Dec 15
The Yankee, Trademark Collection by Wyndham
Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2233)
"D Hotel is a great place to stay. Staff is friendly and the rooms r always clean. We stay there often because it is close to our daughter house. "
United States
Dona
The price is ￥13,259
￥15,404 total
includes taxes & fees
Dec 28 - Dec 29
D. Hotel Suites & Spa
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (980)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ￥14,259
￥15,927 total
includes taxes & fees
Dec 12 - Dec 13
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Reception
Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western

2.5 star property
West Springfield
7.6 out of 10, Good, (103)
"Clean room, friendly staff, good mattress. Not fancy or plush, but perfect for a one or two night place to land while attending events at the Big E. "
United States
Kim
The price is ￥15,726
￥17,998 total
includes taxes & fees
Dec 21 - Dec 22
Baldwin Inn & Suites, SureStay Collection by Best Western
Lobby
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1003)
"Everything was perfect: clean room, great breakfast, courteous staff!"
United States
Tiffany
The price is ￥13,527
￥15,346 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Tru by Hilton Chicopee Springfield
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is ￥20,322
￥22,699 total
includes taxes & fees
Dec 21 - Dec 22
Element Lenox Berkshires
Lobby
Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

2.5 star property
West Springfield
9.6 out of 10, Exceptional, (100)
"Great staff super nice beautiful hotel lots of parking "
United States
Yovelys
The price is ￥17,010
￥19,467 total
includes taxes & fees
Dec 28 - Dec 29
Blue – A Modern Hotel, an Ascend Collection Hotel
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (803)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Room, 2 Queen Beds, Refrigerator | Premium bedding, desk, laptop workspace, blackout drapes
Hampton Inn Westfield

Hampton Inn Westfield

2.5 star property
Westfield
8.4 out of 10, Very Good, (815)
"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
The price is ￥16,403
￥18,322 total
includes taxes & fees
Dec 29 - Dec 30
Hampton Inn Westfield
Lobby sitting area
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, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is ￥15,051
￥16,812 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior
Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG

2.5 star property
West Springfield
8.4 out of 10, Very Good, (792)
"Staff are awesome"
United States
Sherry
The price is ￥13,031
￥14,914 total
includes taxes & fees
Dec 28 - Dec 29
Candlewood Suites West Springfield by IHG
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
The price is ￥11,635
￥12,997 total
includes taxes & fees
Dec 7 - Dec 8
Travelodge by Wyndham Great Barrington Berkshires
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (827)
"Staff was very friendly and helpful."
United States
Pamela
The price is ￥12,255
￥13,688 total
includes taxes & fees
Dec 18 - Dec 19
Howard Johnson by Wyndham Lenox
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is ￥16,010
￥17,884 total
includes taxes & fees
Dec 21 - Dec 22
Hampton Inn & Suites Berkshires-Lenox
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2.0 star property
West Stockbridge
6.8 out of 10, (1002)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is ￥8,074
￥8,857 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Pleasant Valley Motel West Stockbridge
Exterior
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, (1002)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is ￥15,719
￥17,558 total
includes taxes & fees
Dec 15 - Dec 16
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1000)
"Clean room and good breakfast "
United States
Kelly
The price is ￥14,062
￥15,707 total
includes taxes & fees
Dec 28 - Dec 29
Quality Inn
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (778)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
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

Chester Town Hall

You can get tickets for a performance at Chester Town Hall during your trip to Chester. Wander the lakeside and forest in this relaxing area.
See properties

Learn more about Chester

Experience the hiking, camping, and forests in Chester!

See all hotels in Chester
Frozen Sanderson Brook Falls in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

The Ellery

The Ellery

10/10 Excellent
"Breakfast could be improved. Homemade muffins, fresh croissant, etc. "
Joel 1-night trip
Posted 13 hours ago
The Ellery

More cheap stays in Chester

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St West Springfield MA
The price is ￥12,325 per night from Jan 1 to Jan 2
￥12,325
￥14,106 total
Jan 1 - Jan 2, 2026
includes taxes & fees
7/10 Good! (1,020 reviews)

Frequently asked questions

What's the best place to stay in Chester?
La Quinta Inn & Suites by Wyndham Springfield MA, located 22.9 mi (36.8 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 D. Hotel Suites & Spa and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Chester.
What are some of the best vacation rentals in Chester?
Pet Friendly Riverfront Home in Great Barrington: This vacation home rental outside of Chester is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games. See all 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 2 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 Pyramid Lake and Skyline Trail 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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