Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from 2.032.413 ₫

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Top 10 Chester hotels and places to stay

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 2.465.161 ₫
2.753.585 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
8.8 out of 10, Excellent, (703)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
The price is 2.821.697 ₫
3.151.836 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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 2.353.612 ₫
2.629.189 ₫ total
includes taxes & fees
11 Dec - 12 Dec
The Yankee, Trademark Collection by Wyndham

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2230)
"Very clean room, great variety of food at breakfast, friendly and helpful staff."
United States
Liz
The price is 2.254.229 ₫
2.618.718 ₫ total
includes taxes & fees
28 Dec - 29 Dec
D. Hotel Suites & Spa

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very good, (979)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is 2.420.858 ₫
2.704.083 ₫ total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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 2.673.228 ₫
3.059.509 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Baldwin Inn & Suites, SureStay Collection by Best Western

Tru by Hilton Chicopee Springfield

2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1002)
"Everything was perfect: clean room, great breakfast, courteous staff!"
United States
Tiffany
The price is 2.299.551 ₫
2.608.841 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Tru by Hilton Chicopee Springfield

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 3.454.601 ₫
3.858.789 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Element Lenox Berkshires

Blue – A Modern Hotel, an Ascend Collection Hotel

2.5 star property
West Springfield
9.6 out of 10, Exceptional, (98)
"Great staff super nice beautiful hotel lots of parking "
United States
Yovelys
The price is 2.891.580 ₫
3.309.414 ₫ total
includes taxes & fees
25 Dec - 26 Dec
Blue – A Modern Hotel, an Ascend Collection Hotel

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

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 2.805.874 ₫
3.134.162 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn Westfield

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 2.405.035 ₫
2.686.424 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Candlewood Suites West Springfield by IHG

2.5 star property
West Springfield
8.4 out of 10, Very good, (792)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
United States
Christopher
The price is 1.877.758 ₫
2.149.095 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Candlewood Suites West Springfield by IHG

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 1.977.825 ₫
2.209.362 ₫ total
includes taxes & fees
9 Dec - 10 Dec
Travelodge by Wyndham Great Barrington Berkshires

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 2.083.309 ₫
2.326.977 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Howard Johnson by Wyndham 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 2.721.487 ₫
3.039.901 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn & Suites Berkshires-Lenox

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 1.400.300 ₫
1.536.129 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Pleasant Valley Motel West Stockbridge

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 2.668.745 ₫
2.980.989 ₫ total
includes taxes & fees
16 Dec - 17 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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 2.389.476 ₫
2.669.045 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn

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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Chester attractions

Learn more about Chester

Experience the hiking, camping and forests in Chester!

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

Top Chester Hotel Reviews

More cheap stays in Chester

Hotels in Chester with star rating

Frequently asked questions

What's the 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.