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Hotels in Chester

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Choose from 843 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
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! (2,235 reviews)
I love the D but its housecleaning has something to be desired - after first nite - NO bathmat, no washcloths, no Kleenex - room was clean but basics were missing!

Reviewed on Dec 26, 2025

D. Hotel Suites & Spa
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. ...
8.6/10 Excellent! (1,002 reviews)
Wonderful stay in a winter wonderland that evening especially with use of the heated pool and hot tub being maintained! Loved it. Shops inside were lovely as well, bars & restaurant on-site were fun with quirky decor. Whole hotel is quirky, which is fun!

Reviewed on Dec 26, 2025

The Red Lion Inn
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
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (998 reviews)
While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance

Reviewed on Dec 22, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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! (1,002 reviews)
The stay was wonderful! The hotel is VERY clean, comfortable, and the staff are so lovely! I really enjoyed staying here. You're treated like family (in a good way). It is well situated for restaurants and skiing. I will definitely return.

Reviewed on Dec 29, 2025

The Yankee, Trademark Collection by Wyndham
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! (1,002 reviews)
Room was clean and smelled fine.

Reviewed on Nov 30, 2025

Quality Inn West Springfield
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3 out of 5
885 Riverdale Street West Springfield MA
  • 28 min drive from Chester Town Hall
Book a stay at this business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
9/10 Wonderful! (586 reviews)
The hotel was conveniently located, as my child was doing a camp over at Springfield College and we didn’t want to stay right in the city. The room was clean and staff were friendly. The only thing we would have appreciated better would have been breakfast included.

Reviewed on Dec 14, 2025

Courtyard by Marriott West Springfield
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! (796 reviews)
Clean and warm, very spacious and cozy. People here are very nice too! Very good experience here.

Reviewed on Dec 26, 2025

Berkshire Mountain Lodge
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! (823 reviews)
Staff and room were wonderful

Reviewed on Dec 30, 2025

Berkshires Untold
Riverdale Inn

Riverdale Inn

2 out of 5
1500 Riverdale Street 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 MGM Springfield and Olympia Ice Center are ...
5.8/10 (1,000 reviews)
Everything was wonderful and I will be staying here again.

Reviewed on Nov 28, 2025

Riverdale Inn
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! (812 reviews)
We had a great stay! Karaoke in the bar was a blast!! Great little condo!!

Reviewed on Dec 27, 2025

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

Hotel Northampton

3.5 out of 5
36 King Street Northampton MA
  • 9 min drive from Chester Town Hall
Book a stay at this historic hotel in Northampton. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,005 reviews)
Nice historic inn! Great location, walk to restaurants and shopping!!

Reviewed on Dec 29, 2025

Hotel Northampton
Hampton Inn West Springfield

Hampton Inn West Springfield

2.5 out of 5
1011 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 breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,001 reviews)
Yes it was clean

Reviewed on Dec 13, 2025

Hampton Inn West Springfield
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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How many hotels are there in Chester?

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