Find hotels in Chester, MA from ¥9,715

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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, (121 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 ¥13,738
¥15,723 total
includes taxes & fees
Mar 9 - Mar 10
Baldwin Inn & Suites, SureStay Collection by Best Western

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (828 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (573 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is ¥11,816
¥13,199 total
includes taxes & fees
Apr 6 - Apr 7
Travelodge by Wyndham Great Barrington Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (22 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is ¥21,898
¥24,460 total
includes taxes & fees
Apr 6 - Apr 7
Element Lenox Berkshires

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, (1,001 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is ¥17,670
¥19,737 total
includes taxes & fees
Mar 8 - Mar 9
Best Western Plus Berkshire Hills Inn & Suites

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (867 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
The price is ¥14,519
¥16,218 total
includes taxes & fees
Apr 7 - Apr 8
Berkshires Untold

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2,216 reviews)
"Great service, clean & quiet rooms, and a solid breakfast to start the day"
United States
Stephanie
D. Hotel Suites & Spa

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,002 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is ¥13,257
¥14,807 total
includes taxes & fees
Apr 6 - Apr 7
Quality Inn Lee - Lenox South

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very Good, (117 reviews)
"Friendly staff, really nice room, quiet. I really enjoyed my stay."
United States
Desiree
The price is ¥15,596
¥17,420 total
includes taxes & fees
Mar 12 - Mar 13
River Valley Inn

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,008 reviews)
"Friendly clean accommodation were just what we needed. "
United States
Carrie
The price is ¥16,665
¥18,907 total
includes taxes & fees
Mar 15 - Mar 16
Tru by Hilton Chicopee Springfield

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (616 reviews)
"Room was spotless, staff were nice. "
United States
Jose I Medina
The price is ¥18,590
¥20,765 total
includes taxes & fees
Apr 5 - Apr 6
Fairfield Inn & Suites Springfield Holyoke

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 ¥9,216
¥10,110 total
includes taxes & fees
Mar 8 - Mar 9
Pleasant Valley Motel West Stockbridge

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (428 reviews)
"Artful and inspiring interior decorating and delicious French toast for breakfast!"
United States
Marielle
The price is ¥15,936
¥18,080 total
includes taxes & fees
Mar 15 - Mar 16
Naomi's Inn Bed & Breakfast

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, (743 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is ¥16,882
¥18,857 total
includes taxes & fees
Mar 15 - Mar 16
Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is ¥14,596
¥16,304 total
includes taxes & fees
Mar 16 - Mar 17
The Yankee, Trademark Collection by Wyndham

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,001 reviews)
"Clean room, nice staff , decent breakfast. Overall a good stay . "
United States
Anindita
The price is ¥14,216
¥15,879 total
includes taxes & fees
Mar 29 - Mar 30
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
"owners was nice, room was clean"
United States
tom
The price is ¥14,966
¥16,717 total
includes taxes & fees
Mar 8 - Mar 9
Sunset Inn

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (830 reviews)
"I will stay again"
United States
Jailene
The price is ¥18,473
¥20,635 total
includes taxes & fees
Mar 15 - Mar 16
Hampton Inn Westfield

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (836 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is ¥10,887
¥12,160 total
includes taxes & fees
Mar 8 - Mar 9
Howard Johnson by Wyndham Lenox

Best Western Springfield West Inn

Best Western Springfield West Inn
2.5 star property
West Springfield
7.8 out of 10, Good, (1,003 reviews)
"The room was great and jose at the front desk was very kind amd helpful and at the breakfast department he was great."
United States
LUIS
The price is ¥13,862
¥15,866 total
includes taxes & fees
Mar 9 - Mar 10
Best Western Springfield West 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 monuments 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 Berkshires Untold. See all available top hotels, or vacation rentals in Chester.
What are some of the best vacation rentals in Chester?
Family Ski Getaway in the Berkshires: 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 as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. 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 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 Becket Land Trust Historic Quarry 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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