Book 2 Star Hotels in Stockbridge
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Stockbridge 2 Stars Hotels

The Red Lion Inn
30 Main Street, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
0.57 mi from city center
$229 nightly
The price is $256 total per night
$256 total
Aug 27 - Aug 28
Total includes 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 securing valuables, 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

Tanglewood Suites
MA-102, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
0.05 mi from city center
$269 nightly
The price is $269 total per night
$269 total
Aug 6 - Aug 7
Total includes taxes and fees
Tanglewood Suites features a steam room and a garden. You can take advantage of free parking if you drive. Additional amenities include a picnic area and barbecue grills.
Breakfast included
Parking included

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183, Stockbridge, MA
1.29 mi from city center
$425 nightly
The price is $475 total per night
$475 total
Aug 18 - Aug 19
Total includes taxes and fees
Guests of The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood enjoy access to free WiFi in public areas, conference space, and a seasonal outdoor pool. Free parking is included with your stay. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Other amenities at this luxury bed & breakfast include coffee/tea in a common area, a computer station, and a library.
Pool
Breakfast included

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Free Cancellation
Reserve now, pay when you stay
2.58 mi from city center
$136 nightly
The price is $152 total per night
$152 total
Aug 6 - Aug 7
Total includes 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
7.22 mi from city center
$143 nightly
The price is $159 total per night
$159 total
Sep 1 - Sep 2
Total includes 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 water dispenser, and a fireplace in the lobby.
Pet friendly
Parking included

Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
10.13 mi from city center
$119 nightly
The price is $133 total per night
$133 total
Sep 1 - Sep 2
Total includes taxes and fees
Guests of Best Western Plus Berkshire Hills Inn & Suites enjoy a gym, free WiFi in public areas, and conference space. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, dry cleaning/laundry, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a 24-hour business center, coffee/tea in a common area, and a computer station.
Breakfast included
Pet friendly

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Free Cancellation
11.57 mi from city center
$115 nightly
The price is $128 total per night
$128 total
Sep 1 - Sep 2
Total includes 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, tours or tickets, and luggage storage. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly

FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
13.9 mi from city center
$79 nightly
The price is $88 total per night
$88 total
Aug 3 - Aug 4
Total includes taxes and fees
Guests of FairBridge Inn Express enjoy access to free WiFi in public areas, meeting rooms, and a business center. If you drive, put free parking to good use. Front-desk staff are standing by 24/7 to assist with any requests. This motel also has laundry facilities.
Parking included
Free WiFi

Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
19.22 mi from city center
$106 nightly
The price is $119 total per night
$119 total
Aug 25 - Aug 26
Total includes taxes and fees
Vacation Village in the Berkshires features an indoor pool, an outdoor pool, and a children's pool. If you decide to drive, there's free parking. The front desk is staffed 24 hours a day to help with access to locker space and concierge services. Other amenities at this family-friendly condo building include a gym, free WiFi in public areas, and a business center.
Pool
Parking 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.
Stockbridge hotels essential information
Accommodation | 1,380 hotels |
---|---|
Lowest Price | $88 |
Highest Price | $475 |
Popular hotels | The Red Lion Inn, Tanglewood Suites, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, Vacation Village in the Berkshires, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Best Western Plus Berkshire Hills Inn & Suites, FairBridge Inn Express, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Berkshires Untold |
Recent Reviews

Vacation Village in the Berkshires
5/5 Excellent
"Very clean rooms and large and spacious accommodations. Well kept resort. Highly recommend. "
A verified traveler stayed at Vacation Village in the Berkshires
Posted 1 day ago