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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 NT$9,666
NT$11,694 total
includes taxes & fees
Mar 13 - Mar 14

The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,000 reviews)
The price is NT$5,279
NT$7,292 total
includes taxes & fees
Mar 5 - Mar 6

The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
The price is NT$7,459
NT$8,748 total
includes taxes & fees
Mar 13 - Mar 14

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, (845 reviews)
The price is NT$3,778
NT$4,832 total
includes taxes & fees
Mar 9 - Mar 10

The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel8.6 km from Chesterwood
9.2 out of 10, Wonderful, (1,001 reviews)
The price is NT$3,062
NT$3,420 total
includes taxes & fees
Mar 22 - Mar 23

Granville House
Granville House6.4 km from Chesterwood
10.0 out of 10, Exceptional, (96 reviews)
The price is NT$5,435
NT$6,071 total
includes taxes & fees
Mar 10 - Mar 11

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, (740 reviews)
The price is NT$3,342
NT$3,733 total
includes taxes & fees
Mar 5 - Mar 6

Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (824 reviews)

Lakehouse Inn
Lakehouse Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (293 reviews)
The price is NT$4,498
NT$5,275 total
includes taxes & fees
Mar 13 - Mar 14

Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
10.0 out of 10, Exceptional, (136 reviews)

The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (554 reviews)
The price is NT$3,436
NT$3,838 total
includes taxes & fees
Mar 5 - Mar 6

Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (572 reviews)
The price is NT$2,343
NT$2,617 total
includes taxes & fees
Mar 5 - Mar 6

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, (768 reviews)
The price is NT$4,761
NT$5,318 total
includes taxes & fees
Mar 29 - Mar 30

Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
8.4 out of 10, Very Good, (1,001 reviews)
The price is NT$2,673
NT$2,986 total
includes taxes & fees
Mar 22 - Mar 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 NT$1,827
NT$2,005 total
includes taxes & fees
Mar 11 - Mar 12

East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.6 out of 10, Exceptional, (38 reviews)
The price is NT$3,927
NT$4,387 total
includes taxes & fees
Mar 20 - Mar 21

Element Lenox Berkshires
Element Lenox Berkshires12.5 km from Chesterwood
9.6 out of 10, Exceptional, (20 reviews)
The price is NT$4,342
NT$4,850 total
includes taxes & fees
Mar 8 - Mar 9

Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington7.4 km from Chesterwood
6.4 out of 10, (658 reviews)
The price is NT$1,997
NT$2,230 total
includes taxes & fees
Mar 14 - Mar 15
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 | Property class | 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 1,000 reviews | View | ||||||
![]() The Inn at Stockbridge | 9.8 Exceptional 99 reviews | View | ||||||
![]() Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG | 9.0 Wonderful 845 reviews | View | ||||||
![]() The Black Swan Lee - Lenox, an Ascend Collection Hotel | 9.2 Wonderful 1,001 reviews | View |
Top Chesterwood Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
10/10 Excellent
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- Animagic Museum of Animation
- Greenock Country Club
- Visit South Lee
- Norman Rockwell Museum
- Bousquet Ski Area
- Frelinghuysen Morris House and Studio
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- Mission House
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- Charles H. Baldwin & Sons








































































