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Hotels in Chester

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Check Last Minute Chester Hotel Deals

Tonight Mar 22 - Mar 23Next weekend Mar 28 - Mar 30

Choose from 798 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 $132 per night from Mar 30 to Mar 31
$132
includes taxes & fees
Mar 30 - Mar 31
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! (2,332 reviews)
"Clean, updated, super nice staff, good breakfast, close to Northampton (drive)."

Reviewed on Mar 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 $97 per night from Mar 30 to Mar 31
$97
includes taxes & fees
Mar 30 - Mar 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 (1,005 reviews)
"Awesome place"

Reviewed on Mar 21, 2025

Red Roof Inn PLUS+ West 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 Apr 6 to Apr 7
$108
includes taxes & fees
Apr 6 - Apr 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! (535 reviews)
"Motel style building with refreshed modern room. Very clean and the restaurant onsite was good but the breakfast is somewhat limited."

Reviewed on Mar 22, 2025

Life House Berkshires
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 $99 per night from Apr 1 to Apr 2
$99
includes taxes & fees
Apr 1 - Apr 2
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)
"They upgraded our room when they found out it was our wedding night. Everything was so nice, the room was extremely clean and beautiful"

Reviewed on Mar 18, 2025

The Yankee, Trademark Collection by Wyndham
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 $122 per night from Apr 6 to Apr 7
$122
includes taxes & fees
Apr 6 - Apr 7
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! (1,278 reviews)
"My family and me had a good time in this hotel staff friendly rooms clean if could give a 100 stars i would i will come back soon"

Reviewed on Mar 17, 2025

La Quinta Inn & Suites by Wyndham Springfield MA
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
The price is $122 per night from Mar 25 to Mar 26
$122
includes taxes & fees
Mar 25 - Mar 26
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! (1,000 reviews)
"It was great when we were visiting our son at UMass Amherst!"

Reviewed on Mar 15, 2025

Quality Inn & Suites Northampton - Amherst
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
The price is $96 per night from Apr 9 to Apr 10
$96
includes taxes & fees
Apr 9 - Apr 10
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! (669 reviews)
"Great rooms clean and great hot tub and pool"

Reviewed on Mar 17, 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
The price is $147 per night from Mar 23 to Mar 24
$147
includes taxes & fees
Mar 23 - Mar 24
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! (610 reviews)
"I loved it so much to do"

Reviewed on Mar 19, 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
The price is $141 per night from Apr 20 to Apr 21
$141
includes taxes & fees
Apr 20 - Apr 21
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! (976 reviews)
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Reviewed on Mar 19, 2025

Homewood Suites by Hilton Holyoke-Springfield/North
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 Mar 30 to Mar 31
$115
includes taxes & fees
Mar 30 - Mar 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)
"Overall a great stay besides zero hot water. Lots of options to eat. Would stay again."

Reviewed on Mar 6, 2025

Tru by Hilton Chicopee Springfield
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
The price is $116 per night from Mar 28 to Mar 29
$116
includes taxes & fees
Mar 28 - Mar 29
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! (760 reviews)
"Easy check in, nice staff. Rug in the room was kind of musty. They were accommodating to me requesting to have a slightly later check out. Would return if in the area."

Reviewed on Mar 18, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 Apr 14 to Apr 15
$178
includes taxes & fees
Apr 14 - Apr 15
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! (1,001 reviews)
"Loved the Inn. Great place and awesome accommodations. Staff, hotel pets, and the building are amazing."

Reviewed on Mar 20, 2025

The Red Lion 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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How many hotels are there 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.