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Featured Stockbridge Hotels with Air Conditioning

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
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
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
The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street Lee MA
$263 nightly
The price is $294 total per night
$294 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
With a stay at The Inn at Stockbridge in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Berkshire Theatre Festival.
Pool
Breakfast included
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
$189 nightly
The price is $211 total per night
$211 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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
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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
1,348 hotels
Lowest Price
$211
Highest Price
$462
Popular hotels
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, The Inn at Stockbridge, The Red Lion Inn

Most Recent Stockbridge Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

5 out of 5
Posted 16 hours ago
CheapTickets Verified Review
"The rooms were clean and very spacious. The staff went on and above to make our stay a great memory. "
A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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