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Check prices for these dates

Next weekend
17 Jul - 19 Jul
In two weeks
24 Jul - 26 Jul
In one month
7 Aug - 9 Aug
In two months
4 Sept - 6 Sept
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (845 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is HK$487
HK$544 total
includes taxes & fees
6 Aug - 7 Aug
FairBridge Inn Express
Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is HK$998
HK$1,114 total
includes taxes & fees
8 Jul - 9 Jul
The Yankee Inn
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
7.8 out of 10, Good, (223 reviews)
"Front desk staff was very friendly and informative. Great location for the local colleges."
United States
Chris
The price is HK$809
HK$926 total
includes taxes & fees
15 Jul - 16 Jul
Baldwin Inn & Suites, SureStay Collection by Best Western
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 HK$579
HK$635 total
includes taxes & fees
15 Jul - 16 Jul
Pleasant Valley Motel West Stockbridge
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, (180 reviews)
"It's a really nice place to stay!"
United States
Vidita
The price is HK$961
HK$1,074 total
includes taxes & fees
12 Jul - 13 Jul
River Valley Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (578 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is HK$878
HK$981 total
includes taxes & fees
20 Jul - 21 Jul
The Little Lion
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (874 reviews)
"I really enjoyed my stay at the Berkshire Inn, it was safe, clean, and in a convenient part of Pittsfield. Parking was a breeze and I was comfortable in my room. I would definitely book again!"
United States
Hannah
The price is HK$706
HK$788 total
includes taxes & fees
14 Jul - 15 Jul
Berkshire Inn
Individually decorated, individually furnished, iron/ironing board

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (445 reviews)
"He room was very clean, the staff was engaging and the breakfast was delicious. "
United States
John
The price is HK$925
HK$1,050 total
includes taxes & fees
21 Jul - 22 Jul
Naomi's Inn Bed & Breakfast
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (420 reviews)
"Nice place for a stay"
United States
Jay
The price is HK$776
HK$867 total
includes taxes & fees
22 Jul - 23 Jul
Sunset Inn
Lobby

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very good, (1,006 reviews)
"Our room was very clean, staff was very friendly. We would stay here again."
United States
Sherry
The price is HK$830
HK$949 total
includes taxes & fees
21 Jul - 22 Jul
Hampton Inn West Springfield
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, (1,004 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is HK$1,067
HK$1,191 total
includes taxes & fees
2 Aug - 3 Aug
Best Western Plus Berkshire Hills Inn & Suites
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (124 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
The price is HK$1,299
HK$1,451 total
includes taxes & fees
12 Jul - 13 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,005 reviews)
"Clean room and breakfast"
United States
Raphael
The price is HK$1,387
HK$1,899 total
includes taxes & fees
22 Jul - 23 Jul
The Red Lion Inn
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (881 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is HK$776
HK$867 total
includes taxes & fees
16 Jul - 17 Jul
Howard Johnson by Wyndham Lenox
Terrace/patio

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,126 reviews)
"Breakfast was excellent."
United States
Candyce
The price is HK$1,122
HK$1,313 total
includes taxes & fees
14 Jul - 15 Jul
D. Hotel Suites & Spa
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,024 reviews)
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."
United States
Andrew
The price is HK$1,048
HK$1,346 total
includes taxes & fees
6 Aug - 7 Aug
Berkshire Mountain Lodge
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,005 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
The price is HK$1,463
HK$1,634 total
includes taxes & fees
22 Jul - 23 Jul
Berkshires Untold
Living area

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (49 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
United States
Laura
The price is HK$1,216
HK$1,359 total
includes taxes & fees
22 Jul - 23 Jul
East Rock Inn
Lobby

Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield
2.5 star property
West Springfield
7.0 out of 10, Good, (1,009 reviews)
"Love the stay"
United States
Jake
The price is HK$734
HK$840 total
includes taxes & fees
21 Jul - 22 Jul
Red Roof Inn PLUS+ West Springfield
Front of property

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,006 reviews)
"Very nice, clean, love the parking. Great hotel"
United States
Thomas Howard
The price is HK$1,372
HK$1,532 total
includes taxes & fees
12 Jul - 13 Jul
The Ellery
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

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Excelente hotel bonito limpio el personal muy atento y agradable la habitación grande buen aire acondicionado un desayuno variado y exquisito y acabado de preparar"
Melvin 2-night trip
Posted less than an hour ago
D. Hotel Suites & Spa

Find out more about Chester

Chester Resorts information

Number of reviews
15,809
Accommodation
8 Resorts
Lowest Price
HK$544
Highest Price
HK$1,899

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. Has a sauna, a fitness centre and a terrace.
What can I do in Chester?
Experience the local theatre scene at Chester Town Hall, or take the kids to Ashintully Gardens for some family fun. In the area, other attractions include Becket Land Trust Historic Quarry and Littleville Lake.
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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