
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, (111 reviews)
The price is RM1,309
RM1,584 total
includes taxes & fees
14 Jun - 15 Jun

The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,001 reviews)
The price is RM674
RM930 total
includes taxes & fees
9 Jun - 10 Jun

The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (562 reviews)
The price is RM393
RM438 total
includes taxes & fees
3 Jun - 4 Jun

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
9.2 out of 10, Wonderful, (904 reviews)
The price is RM496
RM632 total
includes taxes & fees
9 Jun - 10 Jun

Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (457 reviews)
The price is RM591
RM648 total
includes taxes & fees
2 Jun - 3 Jun

Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (859 reviews)
The price is RM305
RM341 total
includes taxes & fees
7 Jun - 8 Jun

Granville House
Granville House6.4 km from Chesterwood
10.0 out of 10, Exceptional, (101 reviews)
The price is RM793
RM886 total
includes taxes & fees
2 Jun - 3 Jun

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, (767 reviews)
The price is RM539
RM602 total
includes taxes & fees
9 Jun - 10 Jun

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 RM520
RM581 total
includes taxes & fees
4 Jun - 5 Jun

Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (377 reviews)
The price is RM678
RM757 total
includes taxes & fees
3 Jun - 4 Jun

Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (581 reviews)
The price is RM313
RM350 total
includes taxes & fees
2 Jun - 3 Jun

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 RM448
RM501 total
includes taxes & fees
4 Jun - 5 Jun

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, (782 reviews)
The price is RM772
RM862 total
includes taxes & fees
8 Jun - 9 Jun

Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
10.0 out of 10, Exceptional, (138 reviews)
The price is RM1,304
RM1,457 total
includes taxes & fees
4 Jun - 5 Jun

Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge4.7 km from Chesterwood
6.8 out of 10, (1,001 reviews)
The price is RM285
RM313 total
includes taxes & fees
2 Jun - 3 Jun

The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,001 reviews)
The price is RM617
RM710 total
includes taxes & fees
9 Jun - 10 Jun

East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.4 out of 10, Exceptional, (47 reviews)
The price is RM624
RM697 total
includes taxes & fees
14 Jun - 15 Jun

The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (302 reviews)
The price is RM494
RM552 total
includes taxes & fees
3 Jun - 4 Jun

Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington7.4 km from Chesterwood
6.4 out of 10, (664 reviews)
The price is RM282
RM315 total
includes taxes & fees
8 Jun - 9 Jun

Berkshires Untold
Berkshires Untold13 km from Chesterwood
9.0 out of 10, Wonderful, (966 reviews)
The price is RM495
RM553 total
includes taxes & fees
3 Jun - 4 Jun
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 | ||||||
![]() The Little Lion | 8.6 Excellent 562 reviews | View | ||||||
![]() Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG | 9.2 Wonderful 904 reviews | View | ||||||
![]() Shaker Mill Inn | 9.6 Exceptional 457 reviews | View |
Top Chesterwood Hotel Reviews

The Red Lion Inn
10/10 Excellent





































































