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Our top choices for Chesterwood hotels

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 Chesterwood0.4 mi from Chesterwood
9.2 out of 10, Wonderful, (110 reviews)
$335 nightly
The price is $374
Apr 29 - Apr 30
Total with taxes and fees

The Red Lion Inn
The Red Lion Inn2.1 mi from Chesterwood
8.8 out of 10, Excellent, (1,007 reviews)
$192 nightly
The price is $214
Apr 26 - Apr 27
Total with taxes and fees

Shaker Mill Inn
Shaker Mill Inn3.6 mi from Chesterwood
9.6 out of 10, Exceptional, (447 reviews)
$106 nightly
The price is $117
Apr 16 - Apr 17
Total with taxes and fees

The Little Lion
The Little Lion3.2 mi from Chesterwood
8.6 out of 10, Excellent, (555 reviews)
$110 nightly
The price is $123
Apr 16 - Apr 17
Total with taxes and fees

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG5 mi from Chesterwood
8.8 out of 10, Excellent, (755 reviews)
$102 nightly
The price is $114
Apr 23 - Apr 24
Total with taxes and fees

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 IHG4.1 mi from Chesterwood
9.0 out of 10, Wonderful, (872 reviews)
$130 nightly
The price is $145
Apr 28 - Apr 29
Total with taxes and fees

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires5.3 mi from Chesterwood
9.4 out of 10, Exceptional, (777 reviews)
$152 nightly
The price is $170
Apr 20 - Apr 21
Total with taxes and fees

The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel5.3 mi from Chesterwood
9.0 out of 10, Wonderful, (1,001 reviews)
$99 nightly
The price is $111
Apr 26 - Apr 27
Total with taxes and fees

Monument Mountain Motel
Monument Mountain Motel5.4 mi from Chesterwood
9.0 out of 10, Wonderful, (840 reviews)
$67 nightly
The price is $74
Apr 16 - Apr 17
Total with taxes and fees

Devonfield Inn B&B
Devonfield Inn B&B4.7 mi from Chesterwood
10.0 out of 10, Exceptional, (137 reviews)
$299 nightly
The price is $334
Apr 22 - Apr 23
Total with taxes and fees

Quality Inn Great Barrington
Quality Inn Great Barrington6.4 mi from Chesterwood
8.4 out of 10, Very Good, (1,001 reviews)
$67 nightly
The price is $75
Apr 29 - Apr 30
Total with taxes and fees

Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires3.8 mi from Chesterwood
7.6 out of 10, Good, (576 reviews)
$74 nightly
The price is $82
May 14 - May 15
Total with taxes and fees

Chambery Inn
Chambery Inn5.4 mi from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
$190 nightly
The price is $212
Apr 16 - Apr 17
Total with taxes and fees

Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge2.9 mi from Chesterwood
6.8 out of 10, (1,000 reviews)
$70 nightly
The price is $77
Apr 16 - Apr 17
Total with taxes and fees

East Rock Inn
East Rock Inn6.3 mi from Chesterwood
9.4 out of 10, Exceptional, (44 reviews)
$122 nightly
The price is $136
Apr 29 - Apr 30
Total with taxes and fees

The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires6.7 mi from Chesterwood
9.2 out of 10, Wonderful, (1,000 reviews)
$133 nightly
The price is $149
May 3 - May 4
Total with taxes and fees

Berkshires Untold
Berkshires Untold8.1 mi from Chesterwood
9.0 out of 10, Wonderful, (896 reviews)
$87 nightly
The price is $97
Apr 16 - Apr 17
Total with taxes and fees

Element Lenox Berkshires
Element Lenox Berkshires7.8 mi from Chesterwood
9.6 out of 10, Exceptional, (25 reviews)
$147 nightly
The price is $164
Apr 21 - Apr 22
Total with taxes and fees

The Whitlock
The Whitlock6.1 mi from Chesterwood
8.6 out of 10, Excellent, (292 reviews)
$111 nightly
The price is $124
Apr 16 - Apr 17
Total with taxes and fees

Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires7.5 mi from Chesterwood
9.2 out of 10, Wonderful, (616 reviews)
$147 nightly
The price is $164
Apr 19 - Apr 20
Total with taxes and fees
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.
Top Chesterwood Hotel Reviews

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10/10 Excellent
Hotels near other Chesterwood attractions
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