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Recommended hotels in Chester

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.6 out of 10, Excellent, (1000)
"Very friendly and good Breakfast."
United States
Jesse
The price is SAR 286
SAR 320 total
includes taxes & fees
4 Jan - 5 January 2026
Best Western Plus Berkshire Hills Inn & Suites

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
9.8 out of 10, Exceptional, (13)
"New hotel very nice"
United States
joel
The price is SAR 506
SAR 566 total
includes taxes & fees
4 Jan - 5 January 2026
Element Lenox Berkshires

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel
2.5 star property
9.6 out of 10, Exceptional, (109)
"New and still working some kinks out but overall a great stay. "
United States
Jesse
The price is SAR 430
SAR 492 total
includes taxes & fees
22 Jan - 23 January 2026
Blue – A Modern Hotel, an Ascend Collection Hotel

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
8.4 out of 10, Very Good, (1002)
"The staff is always so helpful & nice, and the rooms are always clean and comfortable. This is my favorite place to stay in Lee!"
United States
Cooper
The price is SAR 310
SAR 346 total
includes taxes & fees
11 Jan - 12 January 2026
Quality Inn Lee - Lenox South

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1006)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is SAR 376
SAR 420 total
includes taxes & fees
11 Jan - 12 January 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
7.6 out of 10, Good, (104)
"At the moment breakfast isn’t being served but not a big deal, parking was very easy and close to the entrance not much walking having to be done, staff was very friendly and accommodating the place was very clean and very quiet definitely worth the money in my opinion looking forward to staying again "
United States
Victor
The price is SAR 380
SAR 435 total
includes taxes & fees
29 Dec - 30 Dec
Baldwin Inn & Suites, SureStay Collection by Best Western

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
9.2 out of 10, Wonderful, (1005)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is SAR 284
SAR 317 total
includes taxes & fees
4 Jan - 5 January 2026
The Yankee, Trademark Collection by Wyndham

The Ellery

The Ellery
3.5 star property
9.2 out of 10, Wonderful, (926)
"Clean, lovely staff and breakfast "
United Kingdom
MICHAEL
The price is SAR 462
SAR 516 total
includes taxes & fees
4 Jan - 5 January 2026
The Ellery

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (710)
"Great hospitality "
United States
regina maria
The price is SAR 401
SAR 448 total
includes taxes & fees
4 Jan - 5 January 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Best Western Springfield West Inn

Best Western Springfield West Inn
2.5 star property
7.8 out of 10, Good, (1000)
"Decent breakfast"
United States
Jennifer
The price is SAR 351
SAR 401 total
includes taxes & fees
29 Dec - 30 Dec
Best Western Springfield West Inn

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
8.4 out of 10, Very Good, (817)
"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
The price is SAR 421
SAR 471 total
includes taxes & fees
21 Jan - 22 January 2026
Hampton Inn Westfield

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very Good, (997)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is SAR 348
SAR 388 total
includes taxes & fees
24 Dec - 25 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
9.2 out of 10, Wonderful, (2245)
"Stayed 3 nights, really great hotel and value. "
United States
Vince
The price is SAR 410
SAR 476 total
includes taxes & fees
4 Jan - 5 January 2026
D. Hotel Suites & Spa

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
9.0 out of 10, Wonderful, (1008)
"Everything was perfect: clean room, great breakfast, courteous staff!"
United States
Tiffany
The price is SAR 335
SAR 380 total
includes taxes & fees
1 Jan - 2 January 2026
Tru by Hilton Chicopee Springfield

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
8.2 out of 10, Very Good, (1000)
"nearby eateries"
United States
Majorie
The price is SAR 366
SAR 419 total
includes taxes & fees
25 Dec - 26 Dec
Hampton Inn West Springfield

Motel in Great Barrington

Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (809)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
7.2 out of 10, Good, (903)
"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."
United States
Gloria
The price is SAR 351
SAR 392 total
includes taxes & fees
4 Jan - 5 January 2026
Quality Inn Westfield - Springfield
2.0 star property
6.8 out of 10, (1001)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is SAR 183
SAR 201 total
includes taxes & fees
1 Jan - 2 January 2026
Pleasant Valley Motel West Stockbridge
2.0 star property
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
The price is SAR 281
SAR 314 total
includes taxes & fees
25 Dec - 26 Dec
Travelodge by Wyndham Great Barrington Berkshires

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
2.5 star property
9.2 out of 10, Wonderful, (598)
"Room was very clean, the breakfast was delicious!"
United States
William
The price is SAR 443
SAR 494 total
includes taxes & fees
23 Dec - 24 Dec
Fairfield Inn & Suites Springfield Holyoke
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Top Chester Hotel Reviews