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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 8.152.368 ₫
9.862.239 ₫ total
includes taxes & fees
13 Apr - 14 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 3.532.730 ₫
5.123.117 ₫ total
includes taxes & fees
7 Apr - 8 Apr

Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (446 reviews)
The price is 2.871.387 ₫
3.149.911 ₫ total
includes taxes & fees
30 Mar - 31 Mar

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 2.573.282 ₫
2.874.356 ₫ total
includes taxes & fees
15 Apr - 16 Apr

Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (835 reviews)
The price is 1.576.688 ₫
1.761.096 ₫ total
includes taxes & fees
30 Mar - 31 Mar

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, (752 reviews)
The price is 3.029.560 ₫
3.384.019 ₫ total
includes taxes & fees
21 Apr - 22 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 4.004.136 ₫
4.472.620 ₫ 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 2.897.730 ₫
3.236.764 ₫ total
includes taxes & fees
1 Apr - 2 Apr

Lakehouse Inn
Lakehouse Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (295 reviews)
The price is 3.793.392 ₫
4.449.081 ₫ total
includes taxes & fees
28 Mar - 29 Mar

Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
10.0 out of 10, Exceptional, (137 reviews)
The price is 8.666.847 ₫
9.680.789 ₫ total
includes taxes & fees
28 Mar - 29 Mar

Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
The price is 4.504.561 ₫
5.031.704 ₫ 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, (574 reviews)
The price is 1.975.725 ₫
2.207.017 ₫ total
includes taxes & fees
29 Mar - 30 Mar

The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
The price is 5.974.592 ₫
7.007.501 ₫ total
includes taxes & fees
3 Apr - 4 Apr

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 2.216.763 ₫
2.476.123 ₫ total
includes taxes & fees
22 Apr - 23 Apr

Brook Farm Inn
Brook Farm Inn9.1 km from Chesterwood
9.4 out of 10, Exceptional, (164 reviews)
The price is 4.567.786 ₫
5.233.762 ₫ total
includes taxes & fees
24 Apr - 25 Apr

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 1.541.124 ₫
1.690.613 ₫ total
includes taxes & fees
29 Mar - 30 Mar

East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.4 out of 10, Exceptional, (41 reviews)
The price is 3.525.721 ₫
3.938.230 ₫ total
includes taxes & fees
9 Apr - 10 Apr

Berkshires Untold
Berkshires Untold13 km from Chesterwood
9.0 out of 10, Wonderful, (881 reviews)
The price is 1.839.865 ₫
2.055.095 ₫ total
includes taxes & fees
29 Mar - 30 Mar

Element Lenox Berkshires
Element Lenox Berkshires12.5 km from Chesterwood
9.6 out of 10, Exceptional, (24 reviews)
The price is 3.661.677 ₫
4.090.094 ₫ total
includes taxes & fees
2 Apr - 3 Apr

The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (292 reviews)
The price is 3.319.218 ₫
3.707.567 ₫ total
includes taxes & fees
31 Mar - 1 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 | ||||||
![]() The Red Lion Inn | 8.8 Excellent 1,000 reviews | View | ||||||
![]() Shaker Mill Inn | 9.6 Exceptional 446 reviews | View | ||||||
![]() The Black Swan Lee - Lenox, an Ascend Collection Hotel | 9.2 Wonderful 1,001 reviews | View | ||||||
![]() Monument Mountain Motel | 9.0 Wonderful 835 reviews | View |
Top Chesterwood Hotel Reviews

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




































































