Compare Hotels with Pools in Stockbridge

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Featured Stockbridge Hotels with Pools

The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street Lee MA
$276 nightly
The price is $308 total per night
$308 total
Dec 21 - Dec 22
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
$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
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

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
Dec 28 - Dec 29
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
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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
1,343 hotels
Lowest Price
$217
Highest Price
$462
Popular hotels
The Inn at Stockbridge, The Red Lion Inn, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Most Recent Stockbridge Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

5 out of 5
Posted 1 day 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
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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