Hotels in Chester

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Dec 27 - Dec 28
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Dec 28 - Dec 29
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Top Rated Chester Hotels

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Free Cancellation
19.08 mi from city center
$134 nightly
The price is $149 total per night
$149 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
D. Hotel Suites & Spa features a full-service spa, an indoor pool, and a gym. The front desk has multilingual staff standing by 24 hours a day to assist with dry cleaning/laundry and securing valuables. Other amenities at this spa hotel include a sauna, a hot tub, and a 24-hour business center.
Pool
Hot Tub
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
Free Cancellation
Reserve now, pay when you stay
22.87 mi from city center
$111 nightly
The price is $125 total per night
$125 total
Dec 29 - Dec 30
Total with taxes and fees
At La Quinta Inn & Suites by Wyndham Springfield MA, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to assist with securing valuables and tours/tickets. Other amenities at this family-friendly hotel include meeting rooms, conference space, and a 24-hour business center.
Pool
Breakfast included
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
17.05 mi from city center
$93 nightly
The price is $103 total per night
$103 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests staying at The Yankee, Trademark Collection by Wyndham enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Additional amenities include a hot tub, a seasonal outdoor pool, and coffee/tea in a common area.
Pool
Hot Tub
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
18.3 mi from city center
$88 nightly
The price is $99 total per night
$99 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
Guests of Holiday Inn & Suites Pittsfield-Berkshires by IHG have access to an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The 24-hour front desk has multilingual staff ready to assist with securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
17.02 mi from city center
$177 nightly
The price is $198 total per night
$198 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
Guests of The Red Lion Inn have access to an outdoor pool, a gym, and free WiFi in public areas. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, luggage storage, and dry cleaning/laundry. Other amenities at this historic hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Free Cancellation
Reserve now, pay when you stay
20.56 mi from city center
$79 nightly
The price is $90 total per night
$90 total
Jan 21 - Jan 22, 2026
Total with taxes and fees
Guests of Quality Inn West Springfield enjoy a gym, free WiFi in public areas, and conference space. If you drive, take advantage of free parking. Multilingual staff at the front desk are standing by 24/7 to help with tours or tickets, dry cleaning/laundry, and securing valuables. Other amenities at this golf hotel include a 24-hour business center, a seasonal outdoor pool, and a computer station.
Pool
Breakfast included
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
17.2 mi from city center
$108 nightly
The price is $120 total per night
$120 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
At Berkshire Mountain Lodge, guests have access to an indoor pool, free WiFi in public areas, and a hot tub. If you decide to drive, there's free parking. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this golf lodge include a business center, an arcade/game room, and laundry facilities.
Pool
Hot Tub
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3 out of 5
885 Riverdale Street West Springfield MA
Free Cancellation
Reserve now, pay when you stay
20.87 mi from city center
$118 nightly
The price is $135 total per night
$135 total
Dec 30 - Dec 31
Total with taxes and fees
Guests staying at Courtyard by Marriott West Springfield enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is included with your stay. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and securing valuables. Additional amenities include conference space, a 24-hour business center, and express check-in.
Pool
Parking included
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
16.75 mi from city center
$127 nightly
The price is $142 total per night
$142 total
Jan 20 - Jan 21, 2026
Total with taxes and fees
Renovated in 2023, Berkshires Untold offers free WiFi in public areas, coffee in a common area, and express check-in. You can take advantage of free parking if you drive. The front desk is staffed 24/7 to help with concierge services, and answer any questions about the accommodations. Additional amenities include a terrace, a fireplace in the lobby, and a water dispenser.
Pet friendly
Parking included
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
Free Cancellation
15.06 mi from city center
$145 nightly
The price is $162 total per night
$162 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests staying at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG enjoy features like 2 indoor pools, 2 outdoor pools, and a business center. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this family-friendly hotel include a seasonal outdoor pool, an arcade/game room, and express check-out.
Pool
Air conditioning
Riverdale Inn

Riverdale Inn

2 out of 5
1500 Riverdale Street West Springfield MA
Free Cancellation
Reserve now, pay when you stay
20.17 mi from city center
$68 nightly
The price is $78 total per night
$78 total
Dec 28 - Dec 29
Total with taxes and fees
Riverdale Inn offers free WiFi in public areas and coffee in a common area. Free parking is available if you drive. Front-desk staff are standing by 24/7 to assist with any requests.
Parking included
Free WiFi
Hotel Northampton

Hotel Northampton

3.5 out of 5
36 King Street Northampton MA
Free Cancellation
Reserve now, pay when you stay
18 mi from city center
$165 nightly
The price is $184 total per night
$184 total
Dec 28 - Dec 29
Total with taxes and fees
Guests of Hotel Northampton enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. There's free parking if you drive. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, luggage storage, and dry cleaning/laundry. Other amenities at this historic hotel include conference space, a 24-hour business center, and coffee/tea in a common area.
Parking included
Free WiFi
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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.

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Close to central Chester, you'll find interesting places to visit like Chester Town Hall.

Chester hotels essential information

Accommodation
844 hotels
Lowest Price
$78
Highest Price
$198
Popular hotels
D. Hotel Suites & Spa, La Quinta Inn & Suites by Wyndham Springfield MA, The Yankee, Trademark Collection by Wyndham, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Red Lion Inn, Quality Inn West Springfield, Berkshire Mountain Lodge, Courtyard by Marriott West Springfield, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Riverdale Inn, Hotel Northampton

Recent Reviews

D. Hotel Suites & Spa

D. Hotel Suites & Spa

5/5 Excellent
"The guy at the front desk and the manager were friendly as always, and helpful. I requested to have a different room than I was booked for since I needed a lnormal size fridge and they were understanding and accommodating right on the spot. The room was clean as always"
A verified traveler stayed at D. Hotel Suites & Spa
Posted 2 days ago
D. Hotel Suites & Spa

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