
Find hotels near Chesterwood, South Lee from $64
Check prices for these dates
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
Mar 17 - Mar 18
Total with taxes and fees

The Red Lion Inn
The Red Lion Inn2.1 mi from Chesterwood
8.8 out of 10, Excellent, (1,000 reviews)
$201 nightly
The price is $225
Mar 12 - Mar 13
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, (742 reviews)
$107 nightly
The price is $120
Mar 8 - Mar 9
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, (847 reviews)
$138 nightly
The price is $154
Mar 9 - Mar 10
Total with taxes and fees

Granville House
Granville House4 mi from Chesterwood
10.0 out of 10, Exceptional, (97 reviews)
$174 nightly
The price is $194
Mar 9 - Mar 10
Total with taxes and fees

The Little Lion
The Little Lion3.2 mi from Chesterwood
8.6 out of 10, Excellent, (554 reviews)
$110 nightly
The price is $123
Mar 4 - Mar 5
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
9.2 out of 10, Wonderful, (1,001 reviews)
$98 nightly
The price is $109
Mar 24 - Mar 25
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, (768 reviews)
$152 nightly
The price is $170
Mar 29 - Mar 30
Total with taxes and fees

Monument Mountain Motel
Monument Mountain Motel5.4 mi from Chesterwood
9.0 out of 10, Wonderful, (824 reviews)
$67 nightly
The price is $74
Mar 4 - Mar 5
Total with taxes and fees

Devonfield Inn B&B
Devonfield Inn B&B4.7 mi from Chesterwood
10.0 out of 10, Exceptional, (136 reviews)
$329 nightly
The price is $367
Mar 7 - Mar 8
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, (573 reviews)
$75 nightly
The price is $84
Mar 4 - Mar 5
Total with taxes and fees

Quality Inn Great Barrington
Quality Inn Great Barrington6.4 mi from Chesterwood
8.4 out of 10, Very Good, (1,002 reviews)
$66 nightly
The price is $74
Mar 23 - Mar 24
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
Mar 4 - Mar 5
Total with taxes and fees

Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge2.9 mi from Chesterwood
6.8 out of 10, (1,001 reviews)
$59 nightly
The price is $64
Mar 4 - Mar 5
Total with taxes and fees

Element Lenox Berkshires
Element Lenox Berkshires7.8 mi from Chesterwood
9.8 out of 10, Exceptional, (22 reviews)
$139 nightly
The price is $155
Mar 10 - Mar 11
Total with taxes and fees

Brook Farm Inn
Brook Farm Inn5.7 mi from Chesterwood
9.4 out of 10, Exceptional, (164 reviews)
$153 nightly
The price is $174
Mar 4 - Mar 5
Total with taxes and fees

East Rock Inn
East Rock Inn6.3 mi from Chesterwood
9.6 out of 10, Exceptional, (38 reviews)
$127 nightly
The price is $142
Mar 22 - Mar 23
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, (601 reviews)
$139 nightly
The price is $155
Mar 8 - Mar 9
Total with taxes and fees

The Whitlock
The Whitlock6.1 mi from Chesterwood
8.6 out of 10, Excellent, (290 reviews)
$119 nightly
The price is $133
Mar 4 - Mar 5
Total with taxes and fees

Berkshires Untold
Berkshires Untold8.1 mi from Chesterwood
9.0 out of 10, Wonderful, (866 reviews)
$111 nightly
The price is $124
Mar 5 - Mar 6
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
10/10 Excellent
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