Search for Cheap Deals onHotels in Chester
Choose from 852 Chester Hotel Deals
D. Hotel Suites & Spa
One of the cleanest rooms I had stayed in, in a very long time. The bed was comfortable, and the breakfast was delicious. It was also quiet and you could not hear your neighbors. I would not hesitate to stay here again.
Reviewed on Feb 16, 2026
Berkshire Mountain Lodge
Yes
Reviewed on Feb 15, 2026
The Yankee, Trademark Collection by Wyndham
Pool and hot tub are terrific, great breakfast spread, convenient location, super comfortable mattress. Clean.
Reviewed on Feb 14, 2026
Berkshires Untold
Really cute spaces. Comfy beds and great location.
Reviewed on Feb 16, 2026
Courtyard by Marriott West Springfield
The room was clean. The staff were very friendly. It was nice to have a bar/lounge seating area and the breakfast was good. The hotel was in walking distance to the shopping center and a few restaurants.
Reviewed on Feb 17, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hotel listed their pool was not operational until Jan 31, but learned this was extended upon our arrival on Feb 15. This was an inconvenience as our kids were not happy not to have a pool. Entire hotel need an upgrade as our hot water took about 5 minutes to warm up each time along with other structural ...
Reviewed on Feb 17, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Super clean spacious room!
Reviewed on Feb 15, 2026
Tru by Hilton Chicopee Springfield
Clean room. Decent breakfast. Very friendly staff.
Reviewed on Feb 12, 2026
Quality Inn West Springfield
Clean room, large new shower great water pressure. Felt safe, staff is friendly and helpful.
Reviewed on Feb 20, 2026
The Ellery
Very clean room. Basic but comfortable. Breakfast was fine. Friendly staff. Nice fireplace
Reviewed on Feb 17, 2026
Fairfield Inn & Suites Springfield Northampton/Amherst
The entire facility was very clean. Great location.
Reviewed on Feb 14, 2026
The Red Lion Inn
Love the warmth and lobby’s wood-burning fireplace. Some of the amenities could be updated (EV chargers were broken, the fitness center was messy and missing weights) but there are few inns this charming in New England, and at this price level.
Reviewed on Feb 8, 2026
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