
Hotels near Chesterwood
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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 P18,576
P22,472 total
includes taxes & fees
Apr 21 - Apr 22

The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,001 reviews)
The price is P8,049
P11,673 total
includes taxes & fees
Apr 30 - May 1

Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (446 reviews)
The price is P6,543
P7,177 total
includes taxes & fees
Apr 9 - Apr 10

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, (861 reviews)
The price is P6,776
P8,747 total
includes taxes & fees
Apr 13 - Apr 14

The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (555 reviews)
The price is P6,603
P7,375 total
includes taxes & fees
Apr 9 - Apr 10

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 P9,124
P10,191 total
includes taxes & fees
Apr 20 - Apr 21

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, (754 reviews)
The price is P6,903
P7,711 total
includes taxes & fees
Apr 26 - Apr 27

Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (838 reviews)
The price is P3,593
P4,013 total
includes taxes & fees
Apr 8 - Apr 9

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, (1,003 reviews)
The price is P6,022
P6,726 total
includes taxes & fees
Apr 19 - Apr 20

Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
The price is P10,264
P11,465 total
includes taxes & fees
May 7 - May 8

Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
10.0 out of 10, Exceptional, (137 reviews)
The price is P19,748
P22,059 total
includes taxes & fees
Apr 14 - Apr 15

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 P5,581
P6,234 total
includes taxes & fees
Apr 26 - Apr 27

Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (575 reviews)
The price is P4,502
P5,029 total
includes taxes & fees
Apr 8 - Apr 9

Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge4.7 km from Chesterwood
6.8 out of 10, (1,002 reviews)
The price is P4,268
P4,682 total
includes taxes & fees
Apr 10 - Apr 11

The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
9.0 out of 10, Wonderful, (1,001 reviews)
The price is P8,000
P9,204 total
includes taxes & fees
May 4 - May 5

Element Lenox Berkshires
Element Lenox Berkshires12.5 km from Chesterwood
9.6 out of 10, Exceptional, (25 reviews)
The price is P8,584
P9,588 total
includes taxes & fees
Apr 13 - Apr 14

East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.4 out of 10, Exceptional, (44 reviews)
The price is P7,848
P8,766 total
includes taxes & fees
Apr 27 - Apr 28

Berkshires Untold
Berkshires Untold13 km from Chesterwood
9.0 out of 10, Wonderful, (889 reviews)
The price is P5,551
P6,201 total
includes taxes & fees
Apr 9 - Apr 10

Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires12.1 km from Chesterwood
9.2 out of 10, Wonderful, (613 reviews)
The price is P8,584
P9,588 total
includes taxes & fees
Apr 13 - Apr 14

The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (292 reviews)
The price is P5,976
P6,676 total
includes taxes & fees
Apr 9 - Apr 10
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 1,001 reviews | View | ||||||
![]() Shaker Mill Inn | 9.6 Exceptional 446 reviews | View | ||||||
![]() Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG | 9.0 Wonderful 861 reviews | View | ||||||
![]() The Little Lion | 8.6 Excellent 555 reviews | View |
Top Chesterwood Hotel Reviews

Pleasant Valley Motel West Stockbridge
6/10 Okay






































































