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Independent in Stockbridge
The Red Lion Inn
30 Main Street Stockbridge MA
$194 nightly
The price is $217 total per night
$217 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
0.57 mi from city center
With a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Pool
Spa
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
$414 nightly
The price is $462 total per night
$462 total
Dec 18 - Dec 19
Total with taxes and fees
1.29 mi from city center
When you stay at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood in Stockbridge, you'll be next to a golf course, within a 5-minute drive of Berkshire Botanical Garden and Norman Rockwell Museum.
Pool
Breakfast included
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
$111 nightly
The price is $124 total per night
$124 total
Dec 7 - Dec 8
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
19.22 mi from city center
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain Coaster.
Pool
Parking included
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night
$120 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
9.09 mi from city center
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.
Pool
Hot Tub
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
$92 nightly
The price is $103 total per night
$103 total
Dec 12 - Dec 13
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.57 mi from city center
With a stay at Holiday Inn & Suites Pittsfield-Berkshires by IHG, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center and Berkshire Athenaeum.
Pool
Pet friendly
Berkshires Untold
194 Pittsfield Rd Lenox MA
$114 nightly
The price is $127 total per night
$127 total
Dec 7 - Dec 8
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
7.22 mi from city center
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
Pet friendly
Parking included
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
$145 nightly
The price is $162 total per night
$162 total
Dec 7 - Dec 8
Total with taxes and fees
Free Cancellation
2.58 mi from city center
With a stay at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG in South Lee, you'll be near ski lifts, within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Pool
Air conditioning
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
$89 nightly
The price is $100 total per night
$100 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
8.44 mi from city center
Located in Lenox, The Yankee, Trademark Collection by Wyndham is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.
Pool
Hot Tub
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
$101 nightly
The price is $113 total per night
$113 total
Dec 15 - Dec 16
Total with taxes and fees
Free Cancellation
3.87 mi from city center
With a stay at The Black Swan Lee - Lenox, an Ascend Collection Hotel in Lee, you'll be on the waterfront, within a 10-minute drive of Tanglewood Music Center and Berkshire Mountain Country Store.
Breakfast included
Pet friendly
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
$85 nightly
The price is $95 total per night
$95 total
Dec 8 - Dec 9
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
10.13 mi from city center
Located in Pittsfield, Best Western Plus Berkshire Hills Inn & Suites is a 2-minute drive from Hancock Shaker Village and 5 minutes from Bousquet Ski Area.
Breakfast included
Pet friendly
Hotel On North
297 North Street Pittsfield MA
$133 nightly
The price is $149 total per night
$149 total
Dec 22 - Dec 23
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.91 mi from city center
Located in Pittsfield, Hotel On North is a 1-minute drive from Barrington Stage Company and 7 minutes from Bousquet Ski Area.
Pet friendly
Parking included
Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd Lenox MA
$103 nightly
The price is $115 total per night
$115 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
8.29 mi from city center
Located in Lenox, Hampton Inn & Suites Berkshires-Lenox is in a rural location, within a 5-minute drive of Guido's Marketplace and Kennedy Park.
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.
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Stockbridge hotels essential information
Accommodation | 1,343 hotels |
|---|---|
Lowest Price | $95 |
Highest Price | $462 |
Popular hotels | The Red Lion Inn, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, Vacation Village in the Berkshires, Berkshire Mountain Lodge, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Best Western Plus Berkshire Hills Inn & Suites, Hotel On North, Hampton Inn & Suites Berkshires-Lenox |
Most Recent Stockbridge Hotel Reviews
Holiday Inn & Suites Pittsfield-Berkshires by IHG
5 out of 5
Posted 1 day ago
CheapTickets Verified Review
"I enjoyed the holiday inn. I enjoyed the staff made me fell at home. I enjoyed the comfortable atmosphere and the room was nice and clean. I enjoyed the breakfast very much. The staff was very friendly. "
A verified traveler stayed at Holiday Inn & Suites Pittsfield-Berkshires by IHG
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