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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 Chesterwood0.6 km from Chesterwood
9.2 out of 10, Wonderful, (110 reviews)
The price is ¥48,655
¥58,859 total
includes taxes & fees
Feb 21 - Feb 22

The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,002 reviews)
The price is ¥23,999
¥33,831 total
includes taxes & fees
Mar 3 - Mar 4

Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (445 reviews)
The price is ¥18,211
¥19,977 total
includes taxes & fees
Feb 9 - Feb 10

Granville House
Granville House6.4 km from Chesterwood
10.0 out of 10, Exceptional, (93 reviews)
The price is ¥27,356
¥30,557 total
includes taxes & fees
Feb 9 - Feb 10

The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
The price is ¥37,544
¥44,034 total
includes taxes & fees
Feb 22 - Feb 23

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 IHG6.6 km from Chesterwood
9.0 out of 10, Wonderful, (832 reviews)
The price is ¥16,555
¥21,566 total
includes taxes & fees
Mar 1 - Mar 2

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG8 km from Chesterwood
8.8 out of 10, Excellent, (731 reviews)
The price is ¥16,823
¥18,791 total
includes taxes & fees
Feb 22 - Feb 23

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires8.6 km from Chesterwood
9.4 out of 10, Exceptional, (766 reviews)
The price is ¥23,740
¥26,517 total
includes taxes & fees
Feb 12 - Feb 13

The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (553 reviews)
The price is ¥17,294
¥19,317 total
includes taxes & fees
Feb 9 - Feb 10

Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
10.0 out of 10, Exceptional, (135 reviews)

The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel8.6 km from Chesterwood
9.0 out of 10, Wonderful, (1,002 reviews)
The price is ¥15,368
¥17,167 total
includes taxes & fees
Mar 1 - Mar 2

Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (819 reviews)

Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
8.4 out of 10, Very Good, (1,000 reviews)
The price is ¥13,230
¥14,778 total
includes taxes & fees
Feb 22 - Feb 23

Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge4.7 km from Chesterwood
6.8 out of 10, (1,001 reviews)
The price is ¥9,197
¥10,089 total
includes taxes & fees
Feb 10 - Feb 11

Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (567 reviews)
The price is ¥11,792
¥13,172 total
includes taxes & fees
Feb 9 - Feb 10

East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.6 out of 10, Exceptional, (37 reviews)
The price is ¥19,117
¥21,353 total
includes taxes & fees
Feb 22 - Feb 23

Element Lenox Berkshires
Element Lenox Berkshires12.5 km from Chesterwood
9.8 out of 10, Exceptional, (18 reviews)
The price is ¥21,854
¥24,410 total
includes taxes & fees
Feb 22 - Feb 23
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 445 reviews | View | ||||||
![]() Granville House | 10.0 Exceptional 93 reviews | View | ||||||
![]() The Inn at Stockbridge | 9.8 Exceptional 99 reviews | View |
Top Chesterwood Hotel Reviews

The Little Lion
10/10 Excellent











































































