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Check prices for these dates

This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

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Our top choices for Chester hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

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, (1,003 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is ₩164,818
₩184,102 total
includes taxes & fees
May 31 - Jun 1
Best Western Plus Berkshire Hills Inn & Suites
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Breakfast ok, coffee good, staff great"
United States
Peter
The price is ₩208,497
₩232,887 total
includes taxes & fees
Jun 18 - Jun 19
The Yankee Inn
Standard Room, 2 Queen Beds, Non Smoking | Pillowtop beds, desk, laptop workspace, blackout drapes

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
West Springfield
8.0 out of 10, Very Good, (191 reviews)
"Front desk staff was very friendly and informative. Great location for the local colleges."
United States
Chris
The price is ₩166,003
₩189,990 total
includes taxes & fees
Jun 8 - Jun 9
Baldwin Inn & Suites, SureStay Collection by Best Western
Property amenity

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.8 out of 10, Exceptional, (87 reviews)
"Friendly staff, clean room, awesome breakfast"
United States
Matthew
The price is ₩269,276
₩300,782 total
includes taxes & fees
Jun 16 - Jun 17
TownePlace Suites by Marriott Hadley Amherst
Lobby

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)
"Great location "
United States
Edith
The price is ₩155,323
₩173,488 total
includes taxes & fees
May 31 - Jun 1
Quality Inn Lee - Lenox South
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (99 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is ₩202,497
₩226,189 total
includes taxes & fees
May 31 - Jun 1
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Terrace/patio

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,209 reviews)
"Spacious room, very helpful staff, good coffee and an excellent breakfast."
United States
Clifford
The price is ₩143,557
₩167,973 total
includes taxes & fees
May 31 - Jun 1
D. Hotel Suites & Spa
Lobby

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,001 reviews)
"It was a great stay."
United States
Geovani
The price is ₩178,497
₩202,505 total
includes taxes & fees
Jun 22 - Jun 23
Tru by Hilton Chicopee Springfield
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, (861 reviews)
"very friendly, room was nice and breakfast was great"
United States
Lawrence
The price is ₩189,972
₩212,198 total
includes taxes & fees
Jun 28 - Jun 29
Hampton Inn Westfield
Lobby

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very Good, (1,001 reviews)
"The breakfast was great! The rooms and hallways could be cleaner."
United States
Rasha
The price is ₩137,698
₩157,588 total
includes taxes & fees
Jun 21 - Jun 22
Hampton Inn West Springfield
Room, 2 Queen Beds, 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, (857 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is ₩115,423
₩128,938 total
includes taxes & fees
Jun 3 - Jun 4
Monument Mountain Motel
Studio Suite, Multiple Beds | Desk, laptop workspace, free WiFi, bed sheets

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (159 reviews)
"Friendly staff, great under the radar spot alternative to chain motels!"
United States
Anthony
The price is ₩151,723
₩169,476 total
includes taxes & fees
Jun 1 - Jun 2
River Valley Inn
View from property

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (647 reviews)
"We enjoyed our 3 nights it was quiet and very clean "
United States
Joanne
The price is ₩202,497
₩226,189 total
includes taxes & fees
Jun 11 - Jun 12
Fairfield Inn & Suites Springfield Holyoke
Children's activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
The price is ₩94,499
₩103,666 total
includes taxes & fees
May 29 - May 30
Pleasant Valley Motel West Stockbridge
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (962 reviews)
"Great stay!"
United States
Aditya
The price is ₩160,923
₩179,751 total
includes taxes & fees
Jun 1 - Jun 2
Berkshires Untold
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, (766 reviews)
"Above average hotel breakfast. Very clean hotel."
United States
Helen
The price is ₩203,997
₩227,862 total
includes taxes & fees
Jun 9 - Jun 10
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (958 reviews)
"Clean and great job staffing "
United States
Pedro
The price is ₩174,147
₩228,033 total
includes taxes & fees
May 31 - Jun 1
Berkshire Mountain Lodge
Lobby lounge

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (26 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is ₩272,996
₩304,936 total
includes taxes & fees
Jun 3 - Jun 4
Element by Marriott Lenox Berkshires
Lake

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, (1,000 reviews)
"Clean rooms and lovely view"
Canada
Laraib
The price is ₩189,522
₩211,692 total
includes taxes & fees
Jun 1 - Jun 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Indoor pool

Hampton Inn Chicopee/Springfield

Hampton Inn Chicopee/Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,001 reviews)
"Everything about the hotel was wonderful "
United States
Rosa
The price is ₩178,497
₩202,506 total
includes taxes & fees
Jun 14 - Jun 15
Hampton Inn Chicopee/Springfield
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 monuments in Chester!

See all hotels in Chester
Photo by Chris Addams
Open Photo by Chris Addams

Top Chester Hotel Reviews

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"Great place for the entire family"
Clelia 3-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Springfield MA

More cheap stays in Chester

Hampton Inn West Springfield

Hampton Inn West Springfield

1011 Riverdale St West Springfield MA
The price is ₩137,698 per night from Jun 21 to Jun 22
₩137,698
₩157,588 total
Jun 21 - Jun 22
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)

Frequently asked questions

What's the best place to stay in Chester?
Berkshire Mountain Lodge, located 17.2 mi (27.7 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 Berkshires Untold and Quality Inn West Springfield. 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. There are 870 hotels and other accommodations in the surrounding area. 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 Glendale Falls 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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