Find hotels in Chester, MA from 2.186.826 ₫

  • 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

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, (119 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 2.276.303 ₫
2.605.229 ₫ total
includes taxes & fees
8 Mar - 9 Mar
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, (824 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (20 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is 3.628.178 ₫
4.052.675 ₫ total
includes taxes & fees
12 Mar - 13 Mar
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, (1,005 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is 2.505.531 ₫
2.798.656 ₫ total
includes taxes & fees
1 Mar - 2 Mar
Best Western Plus Berkshire Hills Inn & Suites

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2,238 reviews)
"Great service, clean & quiet rooms, and a solid breakfast to start the day"
United States
Stephanie
D. Hotel Suites & Spa

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very good, (112 reviews)
"Friendly staff, really nice room, quiet. I really enjoyed my stay."
United States
Desiree
The price is 2.584.098 ₫
2.886.438 ₫ total
includes taxes & fees
12 Mar - 13 Mar
River Valley Inn

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 1.531.881 ₫
1.680.474 ₫ total
includes taxes & fees
1 Mar - 2 Mar
Pleasant Valley Motel West Stockbridge

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (614 reviews)
"Room was spotless, staff were nice. "
United States
Jose I Medina
The price is 3.080.036 ₫
3.440.400 ₫ total
includes taxes & fees
29 Mar - 30 Mar
Fairfield Inn & Suites Springfield Holyoke

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (834 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is 1.801.038 ₫
2.011.681 ₫ total
includes taxes & fees
12 Mar - 13 Mar
Howard Johnson by Wyndham Lenox

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel
2.5 star property
West Springfield
9.4 out of 10, Exceptional, (150 reviews)
"Exceptionally clean, loved the massage chair and free shampoo .. the beds were so comfy!"
United States
Jackie
The price is 3.083.951 ₫
3.529.582 ₫ total
includes taxes & fees
20 Mar - 21 Mar
Blue – A Modern Hotel, an Ascend Collection Hotel

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,000 reviews)
"Friendly clean accommodation were just what we needed. "
United States
Carrie
The price is 2.761.070 ₫
3.132.435 ₫ total
includes taxes & fees
4 Mar - 5 Mar
Tru by Hilton Chicopee Springfield

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (864 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
Berkshires Untold

Best Western Springfield West Inn

Best Western Springfield West Inn
2.5 star property
West Springfield
7.8 out of 10, Good, (1,001 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 2.296.715 ₫
2.628.732 ₫ total
includes taxes & fees
25 Mar - 26 Mar
Best Western Springfield West Inn

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,017 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is 2.426.133 ₫
2.709.990 ₫ total
includes taxes & fees
5 Mar - 6 Mar
The Yankee, Trademark Collection by Wyndham

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,005 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is 2.252.081 ₫
2.515.574 ₫ total
includes taxes & fees
26 Mar - 27 Mar
Quality Inn Lee - Lenox South

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (572 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is 1.957.650 ₫
2.186.826 ₫ total
includes taxes & fees
4 Mar - 5 Mar
Travelodge by Wyndham Great Barrington Berkshires

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (844 reviews)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is 2.356.478 ₫
2.632.217 ₫ total
includes taxes & fees
1 Mar - 2 Mar
Berkshire Inn

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, (1,000 reviews)
"Clean room, nice staff , decent breakfast. Overall a good stay . "
United States
Anindita
The price is 2.551.471 ₫
2.849.992 ₫ total
includes taxes & fees
22 Mar - 23 Mar
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (427 reviews)
"Artful and inspiring interior decorating and delicious French toast for breakfast!"
United States
Marielle
The price is 2.644.786 ₫
3.000.654 ₫ total
includes taxes & fees
15 Mar - 16 Mar
Naomi's Inn Bed & Breakfast

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (38 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is 3.636.270 ₫
4.061.713 ₫ total
includes taxes & fees
27 Mar - 28 Mar
East Rock 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.
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 waterfalls 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

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.

Explore a world of travel with Expedia