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Check prices for these dates

Next weekend
29 May - 31 May
In two weeks
5 Jun - 7 Jun
In one month
19 Jun - 21 Jun
In two months
17 Jul - 19 Jul
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Breakfast ok, coffee good, staff great"
United States
Peter
The price is HK$987
HK$1,103 total
includes taxes & fees
3 Jun - 4 Jun
The Yankee Inn
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, (1,000 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is HK$861
HK$962 total
includes taxes & fees
25 May - 26 May
Best Western Plus Berkshire Hills Inn & Suites
Pillow-top beds, desk, laptop workspace, blackout curtains

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, (187 reviews)
"Front desk staff was very friendly and informative. Great location for the local colleges."
United States
Chris
The price is HK$831
HK$951 total
includes taxes & fees
28 May - 29 May
Baldwin Inn & Suites, SureStay Collection by Best Western
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (946 reviews)
"Clean and great job staffing "
United States
Pedro
The price is HK$687
HK$943 total
includes taxes & fees
25 May - 26 May
Berkshire Mountain Lodge
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, (156 reviews)
"Friendly staff, great under the radar spot alternative to chain motels!"
United States
Anthony
The price is HK$792
HK$885 total
includes taxes & fees
14 Jun - 15 Jun
River Valley Inn
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, (96 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 HK$1,026
HK$1,146 total
includes taxes & fees
27 May - 28 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very good, (1,002 reviews)
"The breakfast was great! The rooms and hallways could be cleaner."
United States
Rasha
The price is HK$739
HK$846 total
includes taxes & fees
9 Jun - 10 Jun
Hampton Inn West Springfield
Lobby

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)
"Great location "
United States
Edith
The price is HK$859
HK$959 total
includes taxes & fees
16 Jun - 17 Jun
Quality Inn Lee - Lenox South
Lobby

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,002 reviews)
"It was a great stay."
United States
Geovani
The price is HK$926
HK$1,050 total
includes taxes & fees
22 Jun - 23 Jun
Tru by Hilton Chicopee Springfield
Premium bedding, desk, laptop workspace, blackout curtains

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (859 reviews)
"very friendly, room was nice and breakfast was great"
United States
Lawrence
The price is HK$951
HK$1,062 total
includes taxes & fees
10 Jun - 11 Jun
Hampton Inn Westfield
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (954 reviews)
"Great stay!"
United States
Aditya
The price is HK$978
HK$1,093 total
includes taxes & fees
25 May - 26 May
Berkshires Untold
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (856 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is HK$536
HK$599 total
includes taxes & fees
25 May - 26 May
Monument Mountain Motel
Interior

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
The price is HK$540
HK$1,861 total
includes taxes & fees
27 May - 28 May
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
View from property

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (643 reviews)
"We enjoyed our 3 nights it was quiet and very clean "
United States
Joanne
The price is HK$956
HK$1,068 total
includes taxes & fees
10 Jun - 11 Jun
Fairfield Inn & Suites Springfield Holyoke
Free daily buffet breakfast

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (932 reviews)
" Clean room "
United States
Caitlin
The price is HK$800
HK$894 total
includes taxes & fees
21 Jun - 22 Jun
Quality Inn Westfield - Springfield
In-room safe, desk, free cots/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, (580 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is HK$588
HK$656 total
includes taxes & fees
25 May - 26 May
Travelodge by Wyndham Great Barrington Berkshires
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (561 reviews)
"Avoid this place."
United States
Carole
The price is HK$744
HK$831 total
includes taxes & fees
11 Jun - 12 Jun
The Little Lion
Individually decorated, individually furnished, iron/ironing board

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.2 out of 10, Wonderful, (441 reviews)
"He room was very clean, the staff was engaging and the breakfast was delicious. "
United States
John
The price is HK$924
HK$1,049 total
includes taxes & fees
2 Jun - 3 Jun
Naomi's Inn Bed & Breakfast
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,005 reviews)
"Clean rooms and lovely view"
Canada
Laraib
The price is HK$967
HK$1,081 total
includes taxes & fees
25 May - 26 May
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (856 reviews)
"Clean comfortable room. Very nice staff. Close to everything in downtown Pittsfield. This is the only place I stay when I’m in Pittsfield. Very peaceful. Excellent place to relax. "
United States
Jennifer
The price is HK$627
HK$700 total
includes taxes & fees
25 May - 26 May
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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Top Chester Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"The room is always clean. We enjoy our stay here every time we visit the Berkshires. We also love the food they serve in the motel restaurant. We love how clean and modern the property looks. Would come back here again when we visit Massachusetts."
Preeyus 2-night trip
Posted less than an hour ago
Berkshires Untold

Find out more about Chester

Chester Resorts information

Number of reviews
12,128
Accommodation
8 Resorts
Lowest Price
HK$599
Highest Price
HK$1,861

Frequently asked questions

What is Chester like for a resort holiday?
You deserve a holiday, and a resort is the perfect place to find all the amenities and services you need for a relaxing time in Chester. One of the comfortable resorts in the area might be just what you're looking for, whether you're hoping for an amazing pool, a state-of-the-art fitness centre or fun activities to try.
What's the best resort for my stay in Chester?
Our highest-rated resort near Chester: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 15 mi (24.1 km) from Chester. Enjoy the sauna, fitness centre and terrace.
What can I do in Chester?
Experience the local theatre scene at Chester Town Hall, or take the kids to Berkshire Scenic Railway Museum for some family fun. In the area, other attractions include Littleville Lake and Glendale Falls.
What's the seasonal weather like in Chester?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chester are January, February, November and March, with each month seeing an average of 15 cm of snowfall.
What's the best way to get to and around Chester?
Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) away from the heart of the city. Otherwise, look for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away. If you'd like to venture out around the area, consider renting a car to explore more sights.

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