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Cheap Stockbridge Hotels
The Red Lion Inn
30 Main Street Stockbridge MA
$190 nightly
The price is $212 total per night
$212 total
Jan 14 - Jan 15, 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.
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
Jan 5 - Jan 6, 2026
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
$126 nightly
The price is $141 total per night
$141 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
$88 nightly
The price is $99 total per night
$99 total
Dec 20 - Dec 21
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
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
$92 nightly
The price is $103 total per night
$103 total
Jan 1 - Jan 2, 2026
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
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night
$120 total
Jan 18 - Jan 19, 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
Berkshires Untold
194 Pittsfield Rd Lenox MA
$110 nightly
The price is $123 total per night
$123 total
Dec 21 - Dec 22
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.
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
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
Quality Inn
372 Main Street Great Barrington MA
$76 nightly
The price is $85 total per night
$85 total
Dec 31 - Jan 1, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
6.96 mi from city center
With a stay at Quality Inn Great Barrington in Great Barrington, you'll be near ski lifts, just a 4-minute walk from Mahaiwe Performing Arts Center and 8 minutes by foot from Housatonic River.
Breakfast included
Parking included
Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd Lenox MA
$105 nightly
The price is $117 total per night
$117 total
Jan 4 - Jan 5, 2026
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.
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
$100 nightly
The price is $112 total per night
$112 total
Jan 7 - Jan 8, 2026
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.
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 | $85 |
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, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, Berkshire Mountain Lodge, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Quality Inn, Hampton Inn & Suites Berkshires-Lenox, Holiday Inn Express Hotel & Suites Great Barrington by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel |
Most Recent Stockbridge Hotel Reviews
The Black Swan Lee - Lenox, an Ascend Collection Hotel
5 out of 5
Posted 1 day ago
CheapTickets Verified Review
"Everything was awesome"
A verified traveler stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel
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