
Find hotels near Chesterwood, South Lee from CA $88
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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 CA $423
CA $512 total
includes taxes & fees
Feb 20 - Feb 21

Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (445 reviews)
The price is CA $150
CA $165 total
includes taxes & fees
Feb 8 - Feb 9

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 CA $154
CA $199 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 CA $327
CA $383 total
includes taxes & fees
Feb 22 - Feb 23

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, (1,001 reviews)
The price is CA $134
CA $149 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)

The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (553 reviews)
The price is CA $150
CA $168 total
includes taxes & fees
Feb 8 - Feb 9

Lakehouse Inn
Lakehouse Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (292 reviews)
The price is CA $197
CA $232 total
includes taxes & fees
Feb 27 - Feb 28

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 CA $80
CA $88 total
includes taxes & fees
Feb 8 - Feb 9

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 CA $115
CA $129 total
includes taxes & fees
Feb 27 - Feb 28

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 CA $103
CA $115 total
includes taxes & fees
Feb 8 - Feb 9

Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington7.4 km from Chesterwood
6.4 out of 10, (656 reviews)
The price is CA $87
CA $97 total
includes taxes & fees
Feb 20 - Feb 21

East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.6 out of 10, Exceptional, (37 reviews)
The price is CA $172
CA $193 total
includes taxes & fees
Feb 23 - Feb 24

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 CA $146
CA $163 total
includes taxes & fees
Mar 1 - Mar 2

The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (286 reviews)
The price is CA $134
CA $149 total
includes taxes & fees
Feb 9 - Feb 10

Element Lenox Berkshires
Element Lenox Berkshires12.5 km from Chesterwood
9.8 out of 10, Exceptional, (18 reviews)
The price is CA $191
CA $213 total
includes taxes & fees
Feb 22 - Feb 23

Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires12.1 km from Chesterwood
9.2 out of 10, Wonderful, (599 reviews)
The price is CA $178
CA $199 total
includes taxes & fees
Mar 1 - Mar 2

The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,010 reviews)
The price is CA $134
CA $150 total
includes taxes & fees
Feb 8 - Feb 9
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 | ||||||
![]() Shaker Mill Inn | 9.6 Exceptional 445 reviews | View | ||||||
![]() Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG | 9.0 Wonderful 832 reviews | View | ||||||
![]() The Inn at Stockbridge | 9.8 Exceptional 99 reviews | View | ||||||
![]() The Black Swan Lee - Lenox, an Ascend Collection Hotel | 9.0 Wonderful 1,001 reviews | View |
Top Chesterwood Hotel Reviews

The Red Lion Inn
10/10 Excellent
Hotels near other Chesterwood attractions
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