Book 2 Star Hotels in Chester
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Featured Chester 2 Stars Hotels

Berkshires Untold
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

The Yankee, Trademark Collection by Wyndham
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

Berkshire Mountain Lodge
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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

D. Hotel Suites & Spa
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

Quality Inn West Springfield
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

The Red Lion Inn
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

Courtyard by Marriott West Springfield
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 29 - Dec 30
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

La Quinta Inn & Suites by Wyndham Springfield MA
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
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.
Chester hotels essential information
Accommodation | 844 hotels |
|---|---|
Lowest Price | $90 |
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 |
Recent Reviews

La Quinta Inn & Suites by Wyndham Springfield MA
5/5 Excellent
"Clean room and Bed. BUT the TV definitely needs a upgrade. Very small and outdated "
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Springfield MA
Posted 3 days ago


