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Hotels in Chester

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D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
  • 9 min drive from Chester Town Hall
Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (2,206 reviews)
Nice continental breakfast

Reviewed on Apr 28, 2026

D. Hotel Suites & Spa
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
  • 18 min drive from Chester Town Hall
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (920 reviews)
This “hotel” had so much potential, which honestly made the experience more disappointing. It’s described as a boutique hotel, but in reality it’s more of a refurbished motel with a separate building for the restaurant, lounge, and “front desk.” While the photos make it look charming and thoughtfully ...

Reviewed on Apr 27, 2026

Berkshires Untold
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
  • 22 min drive from Chester Town Hall
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (918 reviews)
From the check in to the check out was amazing. The rooms were very clean and I would come and stay again

Reviewed on Apr 28, 2026

Berkshire Mountain Lodge
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
  • 27 min drive from Chester Town Hall
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,005 reviews)
I feel like the picture has nothing to do with the place. The place was nothing like the picture but when you need something last minute, it is what it is.

Reviewed on Apr 27, 2026

Quality Inn West Springfield
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
  • 7 min drive from Chester Town Hall
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
The Red Lion Inn
Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

2.5 out of 5
1080 Riverdale St West Springfield MA
  • 27 min drive from Chester Town Hall
Book a stay at this business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions MGM Springfield ...
9.6/10 Exceptional! (183 reviews)
Everything was good, room was very clean and smelled good.

Reviewed on Apr 27, 2026

Blue – A Modern Hotel, an Ascend Collection Hotel
River Valley Inn

River Valley Inn

2 out of 5
20 West St West Hatfield MA
  • 16 min drive from Chester Town Hall
Stay at this motel in West Hatfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Pioneer Valley Indoor Karting and Connecticut ...
8.6/10 Excellent! (138 reviews)
This place was a real find. Clean room. Spotless, generous and comfy bedding better than hotel chains (lots of pillows, extra blanket). More than enough towels. We didn't have to request ANYTHING. Walmart and supermarket 5 minutes away. Amherst College and UMass are a little farther away than where ...

Reviewed on Apr 27, 2026

River Valley Inn
The Ellery

The Ellery

3.5 out of 5
259 Elm Street Northampton MA
  • 10 min drive from Chester Town Hall
Stay at this hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (1,003 reviews)
Such a sweet spot, so glad we were able to get a reservation. Wish we'd been hungrier and didn't have breakfast plans , but we did check out the offerings and they were lovely. And the community space was perfect as well, and the opportunity to grab a coffee, tea, cookie, yogurt etc at any hour was ...

Reviewed on Apr 27, 2026

The Ellery
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr Chicopee MA
  • 22 min drive from Chester Town Hall
Stay at this hotel in Chicopee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9/10 Wonderful! (1,014 reviews)
It was a very friendly environment And a beautiful hotel. I rested and enjoyed my stay with my daughter. We created memories this weekend! ❤️

Reviewed on Apr 28, 2026

Tru by Hilton Chicopee Springfield
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
  • 7 min drive from Chester Town Hall
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in ...
9/10 Wonderful! (886 reviews)
We loved our stay at Oak ‘N Spruce. We are an extended family of 15, ranging in age from 3 to 91 years of age, who meet a couple of times a year in the Berkshires. We had 4 units, each with two king bedrooms (one unit was ADA compatible) and it worked out perfectly. We could not believe how much ...

Reviewed on Apr 27, 2026

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
  • 9 min drive from Chester Town Hall
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
9/10 Wonderful! (1,001 reviews)
the place is beautiful and serene. The room is clean and they have all the amenities that you need. Room temperature is perfect.

Reviewed on Apr 14, 2026

The Black Swan Lee - Lenox, an Ascend Collection Hotel
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street Springfield MA
  • 31 min drive from Chester Town Hall
Book a stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8/10 Very Good! (1,288 reviews)
Comfortable stay & great breakfast at a good price

Reviewed on Apr 28, 2026

La Quinta Inn & Suites by Wyndham Springfield MA
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.

Find cheap hotels in Chester

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