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Hotels in Chester

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Check Last Minute Chester Hotel Deals

Tonight May 10 - May 11Next weekend May 16 - May 18

Choose from 823 Chester Hotel Deals

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
Stay at this 3-star 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! (2,278 reviews)

Reviewed on May 5, 2025

D. Hotel Suites & Spa
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
  • 18 min drive from Chester Town Hall
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (583 reviews)
"Great, clean, and updated property. Excellent location."

Reviewed on May 9, 2025

Life House Berkshires
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! (1,281 reviews)
"👍"

Reviewed on May 4, 2025

La Quinta Inn & Suites by Wyndham Springfield MA
Quality Inn West Springfield
Quality Inn West Springfield
2.5 out of 5
1150 Riverdale St, West Springfield, MA
  • 26 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! (1,000 reviews)
"Solid for a night"

Reviewed on May 6, 2025

Quality Inn West Springfield
The Ellery
The Ellery
3.5 out of 5
259 Elm Street, Northampton, MA
  • 10 min drive from Chester Town Hall
Stay at this 3.5-star B&B in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9/10 Wonderful! (672 reviews)
Nice overnight stay
"Very easy to check in, polite staff. The room was large and very clean. The bathroom was updated (but the door didn't close properly). Overall it was a very comfortable stay. The included breakfast options were very good."

Reviewed on May 5, 2025

The Ellery
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
  • 9 min drive from Chester Town Hall
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
9/10 Wonderful! (1,003 reviews)
"THE BREAKFAST WAS SENSATIONAL//STAFF WAS HELPFUL AND FRIENDLY ad said no lakeview but it didn't indicate no balcony-disappointing but maybe I misread ad We would go back but with balcony"

Reviewed on May 9, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
  • 21 min drive from Chester Town Hall
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,001 reviews)
"I had a wonderful stay at The Yankee, Trademark Collection by Wyndham. The room was beautiful and comfortable, making for a very relaxing experience. The staff was incredibly kind, welcoming, and made check-in and check-out effortless. However, during my visit, there was construction happening nearby, ..."

Reviewed on May 7, 2025

The Yankee, Trademark Collection by Wyndham
Quality Inn & Suites Northampton - Amherst
Quality Inn & Suites Northampton - Amherst
2.5 out of 5
117 Conz St, Northampton, MA
  • 9 min drive from Chester Town Hall
Book a stay at this business-friendly hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7/10 Good! (1,001 reviews)
"No problems, could have been a little cleaner in the bathroom but overall great"

Reviewed on May 3, 2025

Quality Inn & Suites Northampton - Amherst
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 ...
8.8/10 Excellent! (1,004 reviews)
"It's a newer hotel with a different concept. Perfect for short or long stays. ( I loved that the rooms didn't have carpet; super clean in my opinion). Would stay again."

Reviewed on May 5, 2025

Tru by Hilton Chicopee Springfield
Candlewood Suites West Springfield by IHG
Candlewood Suites West Springfield by IHG
2.5 out of 5
572 Riverdale St, West Springfield, MA
  • 29 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. Our guests praise the helpful staff ...
8.2/10 Very Good! (692 reviews)
"The gift certificate discounts for a breakfast place is excellent creative thinking. Staff was few, but very nice and helpful to the point of volunteering suggestions. Opposite of pushy, very chill, but well kept nice get away"

Reviewed on Apr 30, 2025

Candlewood Suites West Springfield by IHG
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
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (631 reviews)
"Cleanliness is the best"

Reviewed on May 7, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Homewood Suites by Hilton Holyoke-Springfield/North
Homewood Suites by Hilton Holyoke-Springfield/North
3 out of 5
375 Whitney Ave, Holyoke, MA
  • 22 min drive from Chester Town Hall
Stay at this 3-star business-friendly hotel in Holyoke. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9/10 Wonderful! (998 reviews)
"They were able to have the room ready when we arrived. The staff were pleasant and helpful! It was very convenient for us. 3 hours from home, and my daughter graduating - it was great."

Reviewed on May 5, 2025

Homewood Suites by Hilton Holyoke-Springfield/North
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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