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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 ₹28,758
₹34,789 total
includes taxes & fees
4 May - 5 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 ₹12,739
₹18,391 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 ₹9,873
₹10,831 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 ₹10,243
₹11,442 total
includes taxes & fees
23 Apr - 24 Apr

Granville House
Granville House6.4 km from Chesterwood
10.0 out of 10, Exceptional, (100 reviews)
The price is ₹18,585
₹20,759 total
includes taxes & fees
3 May - 4 May

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, (881 reviews)
The price is ₹10,476
₹13,523 total
includes taxes & fees
26 Apr - 27 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, (758 reviews)
The price is ₹9,499
₹10,609 total
includes taxes & fees
30 Apr - 1 May

Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (842 reviews)
The price is ₹5,867
₹6,553 total
includes taxes & fees
28 Apr - 29 Apr

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, (1,000 reviews)
The price is ₹10,899
₹12,174 total
includes taxes & fees
5 May - 6 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, (777 reviews)
The price is ₹14,155
₹15,811 total
includes taxes & fees
27 Apr - 28 Apr

The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
The price is ₹24,473
₹28,703 total
includes taxes & fees
5 May - 6 May

Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
10.0 out of 10, Exceptional, (137 reviews)
The price is ₹27,785
₹31,035 total
includes taxes & fees
3 May - 4 May

Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
The price is ₹15,889
₹17,748 total
includes taxes & fees
26 Apr - 27 Apr

Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
8.4 out of 10, Very good, (1,002 reviews)
The price is ₹10,129
₹11,314 total
includes taxes & fees
26 Apr - 27 Apr

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 ₹6,969
₹7,785 total
includes taxes & fees
24 Apr - 25 Apr

The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,000 reviews)
The price is ₹12,163
₹13,994 total
includes taxes & fees
5 May - 6 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 ₹6,607
₹7,248 total
includes taxes & fees
22 Apr - 23 Apr

East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.4 out of 10, Exceptional, (44 reviews)
The price is ₹11,094
₹12,392 total
includes taxes & fees
4 May - 5 May

Berkshires Untold
Berkshires Untold13 km from Chesterwood
9.0 out of 10, Wonderful, (907 reviews)
The price is ₹8,381
₹9,362 total
includes taxes & fees
10 May - 11 May

The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (293 reviews)
The price is ₹12,878
₹14,384 total
includes taxes & fees
4 May - 5 May
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 | ||||||
![]() Granville House | 10.0 Exceptional 100 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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