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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, (111 reviews)
The price is ฿9,963
฿12,053 total
includes taxes & fees
10 May - 11 May

The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,001 reviews)
The price is ฿4,404
฿6,358 total
includes taxes & fees
30 Apr - 1 May

Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (447 reviews)
The price is ฿3,509
฿3,850 total
includes taxes & fees
5 May - 6 May

The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (556 reviews)
The price is ฿3,541
฿3,956 total
includes taxes & fees
29 Apr - 30 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, (884 reviews)
The price is ฿3,622
฿4,675 total
includes taxes & fees
30 Apr - 1 May

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, (758 reviews)
The price is ฿3,574
฿3,992 total
includes taxes & fees
4 May - 5 May

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, (778 reviews)
The price is ฿4,894
฿5,466 total
includes taxes & fees
3 May - 4 May

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 ฿3,683
฿4,114 total
includes taxes & fees
11 May - 12 May

Granville House
Granville House6.4 km from Chesterwood
10.0 out of 10, Exceptional, (100 reviews)
The price is ฿6,439
฿7,192 total
includes taxes & fees
3 May - 4 May

Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (845 reviews)
The price is ฿2,202
฿2,460 total
includes taxes & fees
4 May - 5 May

The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
The price is ฿8,461
฿9,923 total
includes taxes & fees
4 May - 5 May

Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
10.0 out of 10, Exceptional, (137 reviews)
The price is ฿8,660
฿9,674 total
includes taxes & fees
28 Apr - 29 Apr

Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
The price is ฿5,505
฿6,149 total
includes taxes & fees
27 May - 28 May

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 ฿3,448
฿3,852 total
includes taxes & fees
17 May - 18 May

Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (576 reviews)
The price is ฿2,415
฿2,697 total
includes taxes & fees
28 Apr - 29 Apr

The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,002 reviews)
The price is ฿4,291
฿4,937 total
includes taxes & fees
3 May - 4 May

Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge4.7 km from Chesterwood
6.8 out of 10, (1,000 reviews)
The price is ฿2,289
฿2,511 total
includes taxes & fees
28 Apr - 29 Apr

Berkshires Untold
Berkshires Untold13 km from Chesterwood
9.0 out of 10, Wonderful, (916 reviews)
The price is ฿2,898
฿3,237 total
includes taxes & fees
27 May - 28 May

East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.4 out of 10, Exceptional, (44 reviews)
The price is ฿4,543
฿5,075 total
includes taxes & fees
28 Apr - 29 Apr

The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (293 reviews)
The price is ฿4,462
฿4,983 total
includes taxes & fees
28 Apr - 29 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 111 reviews | View | ||||||
![]() The Red Lion Inn | 8.8 Excellent 1,001 reviews | View | ||||||
![]() Shaker Mill Inn | 9.6 Exceptional 447 reviews | View | ||||||
![]() The Little Lion | 8.6 Excellent 556 reviews | View | ||||||
![]() Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG | 9.0 Wonderful 884 reviews | View |
Top Chesterwood Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
10/10 Excellent



































































