Hotels near Chesterwood South Lee
Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices
Check prices for these dates
Where to stay near Chesterwood?

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 $309
$374 total
includes taxes & fees
Apr 13 - Apr 14

Inn at Kenmore Hall
Inn at Kenmore Hall12.1 km from Chesterwood
10.0 out of 10, Exceptional, (27 reviews)
The price is $575
$631 total
includes taxes & fees
Mar 31 - Apr 1

The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (555 reviews)
The price is $110
$123 total
includes taxes & fees
Mar 31 - Apr 1

Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
The price is $190
$212 total
includes taxes & fees
Mar 31 - Apr 1

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 $144
$161 total
includes taxes & fees
Apr 12 - Apr 13

Element Lenox Berkshires
Element Lenox Berkshires12.5 km from Chesterwood
9.6 out of 10, Exceptional, (25 reviews)
The price is $139
$155 total
includes taxes & fees
Apr 6 - Apr 7

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, (753 reviews)
The price is $111
$124 total
includes taxes & fees
Apr 9 - Apr 10

Wilder House Berkshires
Wilder House Berkshires19.9 km from Chesterwood
9.8 out of 10, Exceptional, (43 reviews)
The price is $161
$180 total
includes taxes & fees
Apr 2 - Apr 3

Hampton Terrace Inn
Hampton Terrace Inn9.8 km from Chesterwood
9.0 out of 10, Wonderful, (44 reviews)
The price is $252
$281 total
includes taxes & fees
Mar 31 - Apr 1

Berkshires Untold
Berkshires Untold13 km from Chesterwood
9.0 out of 10, Wonderful, (884 reviews)
The price is $87
$97 total
includes taxes & fees
Mar 31 - Apr 1

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 $84
$94 total
includes taxes & fees
Apr 13 - Apr 14

Berkshire Mountain Lodge
Berkshire Mountain Lodge15.9 km from Chesterwood
9.0 out of 10, Wonderful, (890 reviews)
The price is $88
$120 total
includes taxes & fees
Apr 29 - Apr 30

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 $75
$84 total
includes taxes & fees
Mar 31 - Apr 1

Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites16.9 km from Chesterwood
8.6 out of 10, Excellent, (1,000 reviews)
The price is $107
$119 total
includes taxes & fees
Apr 2 - Apr 3

The Central Downtown Inn & Suites
The Central Downtown Inn & Suites19.6 km from Chesterwood
8.6 out of 10, Excellent, (359 reviews)
The price is $102
$114 total
includes taxes & fees
Mar 31 - Apr 1

Sunset Inn
Sunset Inn9.1 km from Chesterwood
7.6 out of 10, Good, (411 reviews)
The price is $95
$106 total
includes taxes & fees
Mar 31 - Apr 1

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG19.8 km from Chesterwood
8.0 out of 10, Very Good, (1,002 reviews)
The price is $123
$137 total
includes taxes & fees
Apr 2 - Apr 3

The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,000 reviews)
The price is $149
$211 total
includes taxes & fees
Apr 7 - Apr 8

Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (446 reviews)
The price is $109
$120 total
includes taxes & fees
Mar 31 - Apr 1

Granville House
Granville House6.4 km from Chesterwood
10.0 out of 10, Exceptional, (97 reviews)
The price is $174
$194 total
includes taxes & fees
Apr 2 - Apr 3
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 | ||||||
![]() Inn at Kenmore Hall | 10.0 Exceptional 27 reviews | View | ||||||
![]() The Little Lion | 8.6 Excellent 555 reviews | View | ||||||
![]() Chambery Inn | 9.6 Exceptional 376 reviews | View | ||||||
![]() Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires | 9.4 Exceptional 776 reviews | View |

































































