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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 SAR 1,161
SAR 1,405 total
includes taxes & fees
17 Apr - 18 Apr

Granville House
Granville House6.4 km from Chesterwood
10.0 out of 10, Exceptional, (97 reviews)
The price is SAR 653
SAR 729 total
includes taxes & fees
2 Apr - 3 Apr

Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
10.0 out of 10, Exceptional, (137 reviews)
The price is SAR 1,235
SAR 1,379 total
includes taxes & fees
6 Apr - 7 Apr

Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (446 reviews)
The price is SAR 376
SAR 413 total
includes taxes & fees
9 Apr - 10 Apr

Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
The price is SAR 642
SAR 717 total
includes taxes & fees
2 Apr - 3 Apr

The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,000 reviews)
The price is SAR 503
SAR 730 total
includes taxes & fees
14 Apr - 15 Apr

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, (776 reviews)
The price is SAR 540
SAR 604 total
includes taxes & fees
12 Apr - 13 Apr

Brook Farm Inn
Brook Farm Inn9.1 km from Chesterwood
9.4 out of 10, Exceptional, (164 reviews)
The price is SAR 605
SAR 694 total
includes taxes & fees
4 Apr - 5 Apr

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, (860 reviews)
The price is SAR 422
SAR 545 total
includes taxes & fees
14 Apr - 15 Apr

Prospect Berkshires
Prospect Berkshires12.8 km from Chesterwood
9.8 out of 10, Exceptional, (23 reviews)
The price is SAR 1,182
SAR 1,446 total
includes taxes & fees
14 Apr - 15 Apr

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 SAR 370
SAR 413 total
includes taxes & fees
9 Apr - 10 Apr

Inn at Kenmore Hall
Inn at Kenmore Hall12.1 km from Chesterwood
10.0 out of 10, Exceptional, (27 reviews)
The price is SAR 2,158
SAR 2,367 total
includes taxes & fees
2 Apr - 3 Apr

East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.4 out of 10, Exceptional, (41 reviews)
The price is SAR 445
SAR 498 total
includes taxes & fees
14 Apr - 15 Apr

The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (555 reviews)
The price is SAR 409
SAR 456 total
includes taxes & fees
13 Apr - 14 Apr

Element Lenox Berkshires
Element Lenox Berkshires12.5 km from Chesterwood
9.6 out of 10, Exceptional, (25 reviews)
The price is SAR 522
SAR 583 total
includes taxes & fees
7 Apr - 8 Apr

Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (836 reviews)
The price is SAR 225
SAR 251 total
includes taxes & fees
2 Apr - 3 Apr

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, (753 reviews)
The price is SAR 417
SAR 465 total
includes taxes & fees
14 Apr - 15 Apr

Hampton Terrace Inn
Hampton Terrace Inn9.8 km from Chesterwood
9.0 out of 10, Wonderful, (44 reviews)
The price is SAR 821
SAR 918 total
includes taxes & fees
9 Apr - 10 Apr

Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires12.1 km from Chesterwood
9.2 out of 10, Wonderful, (611 reviews)
The price is SAR 552
SAR 616 total
includes taxes & fees
13 Apr - 14 Apr

The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
9.0 out of 10, Wonderful, (1,000 reviews)
The price is SAR 495
SAR 570 total
includes taxes & fees
9 Apr - 10 Apr
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 | ||||||
![]() Granville House | 10.0 Exceptional 97 reviews | View | ||||||
![]() Devonfield Inn B&B | 10.0 Exceptional 137 reviews | View | ||||||
![]() Shaker Mill Inn | 9.6 Exceptional 446 reviews | View | ||||||
![]() Chambery Inn | 9.6 Exceptional 376 reviews | View |
Top Chesterwood Hotel Reviews

Family Ski Getaway in the Berkshires
10/10 Excellent
Hotels near other Chesterwood attractions
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Other Hotels near Chesterwood, South Lee
Explore more hotels
- Stockbridge pied-à-terre
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- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Walk into town, soak up sun on enclosed porch & steps away from nature trails!
- Stockbridge Village in Summer
- Family Ski Getaway in the Berkshires
- Pleasant Valley Motel West Stockbridge
- Stockbridge Village Cottage With Mountain View’s and walk to town
- The Little Lion
- Beautiful House in the Woods: Huge Yard, Hot Tub
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- The Inn at Stockbridge








































































