
Find hotels near Chesterwood, South Lee from $74
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Our top choices for Chesterwood hotels

The Red Lion Inn
The Red Lion Inn2.1 mi from Chesterwood
8.8 out of 10, Excellent, (1,001 reviews)
$171 nightly
The price is $191
Apr 30 - May 1
Total with taxes and fees

Shaker Mill Inn
Shaker Mill Inn3.6 mi from Chesterwood
9.6 out of 10, Exceptional, (447 reviews)
$100 nightly
The price is $110
Apr 27 - Apr 28
Total with taxes and fees

The Little Lion
The Little Lion3.2 mi from Chesterwood
8.6 out of 10, Excellent, (556 reviews)
$108 nightly
The price is $120
May 6 - May 7
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, (758 reviews)
$102 nightly
The price is $114
Apr 30 - May 1
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, (778 reviews)
$152 nightly
The price is $170
Apr 28 - Apr 29
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, (883 reviews)
$130 nightly
The price is $145
Apr 26 - Apr 27
Total with taxes and fees

Granville House
Granville House4 mi from Chesterwood
10.0 out of 10, Exceptional, (100 reviews)
$200 nightly
The price is $223
May 3 - May 4
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, (1,000 reviews)
$110 nightly
The price is $123
Apr 30 - May 1
Total with taxes and fees

Monument Mountain Motel
Monument Mountain Motel5.4 mi from Chesterwood
9.0 out of 10, Wonderful, (844 reviews)
$67 nightly
The price is $74
Apr 27 - Apr 28
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 26 - Apr 27
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 6 - May 7
Total with taxes and fees

Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South5.7 mi from Chesterwood
8.4 out of 10, Very Good, (1,001 reviews)
$99 nightly
The price is $110
May 19 - May 20
Total with taxes and fees

Chambery Inn
Chambery Inn5.4 mi from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
$185 nightly
The price is $207
May 6 - May 7
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)
$69 nightly
The price is $76
May 6 - May 7
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, (1,001 reviews)
$133 nightly
The price is $149
May 3 - May 4
Total with taxes and fees

East Rock Inn
East Rock Inn6.3 mi from Chesterwood
9.4 out of 10, Exceptional, (44 reviews)
$130 nightly
The price is $145
Apr 30 - May 1
Total with taxes and fees

Berkshires Untold
Berkshires Untold8.1 mi from Chesterwood
9.0 out of 10, Wonderful, (909 reviews)
$87 nightly
The price is $97
Apr 26 - Apr 27
Total with taxes and fees

The Whitlock
The Whitlock6.1 mi from Chesterwood
8.6 out of 10, Excellent, (293 reviews)
$148 nightly
The price is $165
Apr 26 - Apr 27
Total with taxes and fees

Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington4.6 mi from Chesterwood
6.4 out of 10, (662 reviews)
$71 nightly
The price is $79
Apr 30 - May 1
Total with taxes and fees

The Berkshire Mountain Inn
The Berkshire Mountain Inn6.7 mi from Chesterwood
9.8 out of 10, Exceptional, (6 reviews)
$173 nightly
The price is $193
Apr 26 - Apr 27
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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