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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 26 - Apr 27
Total with taxes and fees

The Red Lion Inn
The Red Lion Inn2.1 mi from Chesterwood
8.8 out of 10, Excellent, (1,002 reviews)
$189 nightly
The price is $211
Apr 21 - Apr 22
Total with taxes and fees

Shaker Mill Inn
Shaker Mill Inn3.6 mi from Chesterwood
9.6 out of 10, Exceptional, (447 reviews)
$108 nightly
The price is $118
Apr 14 - Apr 15
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, (754 reviews)
$107 nightly
The price is $120
Apr 20 - Apr 21
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 13 - Apr 14
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, (864 reviews)
$130 nightly
The price is $145
Apr 29 - Apr 30
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 19 - Apr 20
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, (1,002 reviews)
$100 nightly
The price is $112
Apr 19 - Apr 20
Total with taxes and fees

Monument Mountain Motel
Monument Mountain Motel5.4 mi from Chesterwood
9.0 out of 10, Wonderful, (839 reviews)
$67 nightly
The price is $74
Apr 14 - Apr 15
Total with taxes and fees

Granville House
Granville House4 mi from Chesterwood
10.0 out of 10, Exceptional, (98 reviews)
$174 nightly
The price is $194
Apr 13 - Apr 14
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 14 - Apr 15
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, (1,000 reviews)
$93 nightly
The price is $104
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)
$75 nightly
The price is $84
Apr 13 - Apr 14
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 13 - Apr 14
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)
$71 nightly
The price is $78
Apr 14 - Apr 15
Total with taxes and fees

Berkshires Untold
Berkshires Untold8.1 mi from Chesterwood
9.0 out of 10, Wonderful, (895 reviews)
$87 nightly
The price is $97
Apr 13 - Apr 14
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

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 27 - Apr 28
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 19 - Apr 20
Total with taxes and fees

Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington4.6 mi from Chesterwood
6.4 out of 10, (661 reviews)
$67 nightly
The price is $75
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.
Compare popular hotels close to Chesterwood
Property | Star rating | Guest rating | Breakfast included | Pool | Spa | Pet friendly | WiFi included | |
|---|---|---|---|---|---|---|---|---|
![]() The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood | 9.2 Wonderful 110 reviews | View | ||||||
![]() The Red Lion Inn | 8.8 Excellent 1,002 reviews | View | ||||||
![]() Shaker Mill Inn | 9.6 Exceptional 447 reviews | View | ||||||
![]() Holiday Inn Express Hotel & Suites Great Barrington by IHG | 8.8 Excellent 754 reviews | View | ||||||
![]() The Little Lion | 8.6 Excellent 555 reviews | View |
Top Chesterwood Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
10/10 Excellent
Hotels near other Chesterwood attractions
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