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Hotels in Chester

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Check Last Minute Chester Hotel Deals

Tonight Jan 24 - Jan 25This weekend Jan 24 - Jan 26

Choose from 792 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
The price is $143 per night from Jan 26 to Jan 27
$143
includes taxes & fees
Jan 26 - Jan 27
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! (2,345 reviews)
Great stay at the D!
"Had a great time and had great service. We really enjoyed the food and the service at the Delaney House as well!"

Reviewed on Jan 20, 2025

D. Hotel Suites & Spa
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
The price is $104 per night from Jan 30 to Jan 31
$104
includes taxes & fees
Jan 30 - Jan 31
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 (1,003 reviews)
"Thank you so much !!"

Reviewed on Jan 20, 2025

Red Roof Inn PLUS+ 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
The price is $115 per night from Jan 30 to Jan 31
$115
includes taxes & fees
Jan 30 - Jan 31
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! (1,000 reviews)
"Brilliant"

Reviewed on Jan 21, 2025

Tru by Hilton Chicopee Springfield
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
  • 18 min drive from Chester Town Hall
The price is $108 per night from Feb 6 to Feb 7
$108
includes taxes & fees
Feb 6 - Feb 7
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! (480 reviews)
"This was a very clean and beautifully decorated property. I loved the lobby especially. It's a nice place to hang out and read or work. The room was very nice, but the AC/Heating unit was VERY loud and kept going on and off, which kept me awake. I finally turned it off, which meant I had not heat. ..."

Reviewed on Jan 23, 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
The price is $123 per night from Jan 29 to Jan 30
$123
includes taxes & fees
Jan 29 - Jan 30
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 ...
8.2/10 Very Good! (1,271 reviews)
Great place
"Perfect place to stay while in Springfield. Clean, comfortable, essy to get to, and close to area attractions. Complimentary hot breakfast buffet, but also has a very convenient drive-thru Dunkin' Donuts in a connecting parking lot! Looking forward to our next stay."

Reviewed on Jan 19, 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
The price is $92 per night from Feb 6 to Feb 7
$92
includes taxes & fees
Feb 6 - Feb 7
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)
Definitely would go back and recommend
"Very clean and comfortable l. Very quiet also. Breakfast was great kids loved it."

Reviewed on Dec 25, 2024

Quality Inn West Springfield
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
The price is $115 per night from Feb 2 to Feb 3
$115
includes taxes & fees
Feb 2 - Feb 3
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)
"Had a great time at this hotel. The rooms are comfortable. The staff is very friendly. Ended up spending Friday and Saturday night hanging out in the bar in the hotel where Carl and George kept us entertained. We had a lot of unexpected fun (I’m not one to hang out in a bar but felt at home)"

Reviewed on Jan 19, 2025

The Yankee, Trademark Collection by Wyndham
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 out of 5
190 Meadow Street, South Lee, MA
  • 7 min drive from Chester Town Hall
The price is $147 per night from Jan 27 to Jan 28
$147
includes taxes & fees
Jan 27 - Jan 28
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our ...
8.8/10 Excellent! (588 reviews)
"Plenty of room. Good location to local skiing. Clean."

Reviewed on Jan 21, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
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
The price is $178 per night from Feb 13 to Feb 14
$178
includes taxes & fees
Feb 13 - Feb 14
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,000 reviews)
"Little disappointed with the service in the Dining Room. Bar closed early which was disappointing in the sense there was nothing to do after hours."

Reviewed on Jan 14, 2025

The Red Lion Inn
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
The price is $113 per night from Jan 30 to Jan 31
$113
includes taxes & fees
Jan 30 - Jan 31
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! (1,002 reviews)
Great affordable but nice option
"Excellent affordable option with a very pretty view of the lake. The 24 hour coffee and tea stand was also great. Staff were very polite and helpful. Room was very clean. Would definitely stay here again."

Reviewed on Jan 19, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3 out of 5
One West Street, Pittsfield, MA
  • 28 min drive from Chester Town Hall
The price is $118 per night from Jan 31 to Feb 1
$118
includes taxes & fees
Jan 31 - Feb 1
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! (727 reviews)
Reliable, friendly
"Appreciated that the hotel offered free valet, especially given how cold it was. Check in was fast, courteous. Room was spacious and clean. Breakfast was good, reasonably priced. Check out was speedy and friendly. Hotel was still decorated for the holidays which made it festive looking. Could use ..."

Reviewed on Jan 13, 2025

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
The Ellery
The Ellery
3.5 out of 5
259 Elm Street, Northampton, MA
  • 10 min drive from Chester Town Hall
The price is $155 per night from Jan 26 to Jan 27
$155
includes taxes & fees
Jan 26 - Jan 27
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! (585 reviews)
Nice hotel
"This was a nice hotel. Clean and very friendly and helpful staff. Breakfast was ok. Typical continental breakfast. Fireplace on for breakfast only. Nice cozy place. I would stay again for sure."

Reviewed on Jan 23, 2025

The Ellery
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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