Book 2 Star Hotels in Chester
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Featured Chester 2 Stars Hotels

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
Free Cancellation
15.06 mi from city center
$130 nightly
The price is $145 total per night
$145 total
Mar 1 - Mar 2
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

Berkshires Untold
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
16.75 mi from city center
$98 nightly
The price is $110 total per night
$110 total
Mar 8 - Mar 9
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
Feb 22 - Feb 23
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 tours or tickets, 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
$121 nightly
The price is $136 total per night
$136 total
Mar 12 - Mar 13
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
18.3 mi from city center
$102 nightly
The price is $114 total per night
$114 total
Mar 7 - Mar 8
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 dry cleaning/laundry, luggage storage, and tours or tickets. 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
Reserve now, pay when you stay
19.08 mi from city center
$121 nightly
The price is $135 total per night
$135 total
Feb 11 - Feb 12
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

The Red Lion Inn
30 Main Street Stockbridge MA
17.02 mi from city center
$183 nightly
The price is $205 total per night
$205 total
Mar 4 - Mar 5
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 concierge services, securing valuables, 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
Feb 19 - Feb 20
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

Tru by Hilton Chicopee Springfield
440 Memorial Dr Chicopee MA
Free Cancellation
Reserve now, pay when you stay
21.78 mi from city center
$98 nightly
The price is $111 total per night
$111 total
Mar 2 - Mar 3
Total with taxes and fees
At Tru by Hilton Chicopee Springfield, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. You can take advantage of free parking if you drive. Front-desk staff can answer questions 24/7, and assist with dry cleaning/laundry, luggage storage, and securing valuables. Additional amenities include a 24-hour business center, an arcade/game room, and free newspapers.
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 | 851 hotels |
|---|---|
Lowest Price | $103 |
Highest Price | $205 |
Popular hotels | D. Hotel Suites & Spa, Berkshire Mountain Lodge, The Yankee, Trademark Collection by Wyndham, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Courtyard by Marriott West Springfield, Tru by Hilton Chicopee Springfield, The Red Lion Inn |
Recent Reviews

Berkshires Untold
5/5 Excellent
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
A verified traveler stayed at Berkshires Untold
Posted 19 hours ago


