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Cheap Stockbridge Hotels
The Red Lion Inn
30 Main Street Stockbridge MA
$193 nightly
The price is $216 total per night
$216 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 28 - Dec 29
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 9 - Dec 10
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 5 - Jan 6, 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
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
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
$89 nightly
The price is $100 total per night
$100 total
Dec 15 - Dec 16
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
Berkshires Untold
194 Pittsfield Rd Lenox MA
$113 nightly
The price is $126 total per night
$126 total
Dec 14 - Dec 15
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
$152 nightly
The price is $169 total per night
$169 total
Dec 9 - Dec 10
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 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 17 - Dec 18
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
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
Holiday Inn Express Hotel & Suites Great Barrington by IHG
415 Stockbridge Rd Great Barrington MA
$107 nightly
The price is $120 total per night
$120 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
Free Cancellation
5.29 mi from city center
With a stay at Holiday Inn Express Hotel & Suites Great Barrington by IHG in Great Barrington, you'll be on a river, just steps from Housatonic River and a 3-minute drive from Monument Mountain Reservation.
Pool
Breakfast included
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
$93 nightly
The price is $104 total per night
$104 total
Dec 14 - Dec 15
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
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 | 1,344 hotels |
|---|---|
Lowest Price | $100 |
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, The Yankee, Trademark Collection by Wyndham, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Hampton Inn & Suites Berkshires-Lenox, Holiday Inn Express Hotel & Suites Great Barrington by IHG, Best Western Plus Berkshire Hills Inn & Suites |
Most Recent Stockbridge Hotel Reviews
Holiday Inn Express Hotel & Suites Great Barrington by IHG
5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"We stay here every year and it never disappoints "
A verified traveler stayed at Holiday Inn Express Hotel & Suites Great Barrington by IHG
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