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Hotels in Chester

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Choose from 838 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! (2,247 reviews)
"Third time staying love the pool, and the staff is always ready to help with a smile. This has become our family’s spot. Kudos to housekeeping for the great job they do. A++"

Reviewed on Jul 17, 2025

D. Hotel Suites & Spa
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! (1,274 reviews)
"Plenty of free, convenient parking . Helpful, friendly staff . Clean , comfortable , great AC in the room."

Reviewed on Jul 17, 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! (1,004 reviews)
"Great staff went above and beyond. I will continue to rebook the room. Great price and super easy access from I91"

Reviewed on Jul 18, 2025

Quality Inn West Springfield
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! (1,007 reviews)
"Staff is very accommodating and friendly"

Reviewed on Jul 18, 2025

Tru by Hilton Chicopee Springfield
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street, West Springfield, MA
  • 26 min drive from Chester Town Hall
Stay at this hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,000 reviews)
"Perfect place to relax for the night. Clean, right off a main road, convenient location."

Reviewed on Jul 14, 2025

Red Roof Inn PLUS+ West Springfield
Berkshires Untold

Berkshires Untold

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! (640 reviews)
"We enjoyed the unique character and flavor of the hotel!"

Reviewed on Jul 19, 2025

Berkshires Untold
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! (678 reviews)
"Terrific place. Spacious, clean, comfortable."

Reviewed on Jul 18, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
  • 28 min drive from Chester Town Hall
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (823 reviews)
Very solid spot
"Great spot for exploring the area. Walking distance to downtown, and easy drive to nature, which is why I was in town w/ friends. Only complaint is that the hot water ran out really fast in the showers the days we were there"

Reviewed on Jul 16, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
  • 22 min drive from Chester Town Hall
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (519 reviews)
"Superb lodging and a nice reprieve. Not sure who invited the elephants to stay in the room above me but otherwise a great stopover!!"

Reviewed on Jul 18, 2025

Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
  • 32 min drive from Chester Town Hall
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
5.2/10 (743 reviews)
"Rooms were much nicer than expected. Despite the somewhat dated exterior and overall first impression from the outside, the rooms were solidly good, clean, and comfortable. Good value for the price."

Reviewed on Jul 1, 2025

FairBridge Inn Express
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
  • 26 min drive from Chester Town Hall
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,008 reviews)
"Very friendly girl at the check-in who moved us (essentially upgraded us) to a suite after our initial room smelled of lingering cigarette smoke. She was very patient about my paranoia over the pilot light/flame in the room's fireplace. Great experience."

Reviewed on Jul 18, 2025

Best Western Plus Berkshire Hills Inn & Suites
Riverdale Inn

Riverdale Inn

2 out of 5
1500 Riverdale Street, On Route 5, West Springfield, MA
  • 25 min drive from Chester Town Hall
Stay at this motel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Big E and MGM Springfield are located ...
5.8/10 (1,001 reviews)
"Entrance was super hard to find at night, and you have to drive a mile to the next u-turn."

Reviewed on Jul 19, 2025

Riverdale 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.

Find cheap hotels in Chester

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Finding a cheap car rental deal in Chester is as easy as scoring cheap hotels in Chester. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.