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Our top choices for Chesterwood hotels

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 ¥11,645
¥12,774 total
includes taxes & fees
Jun 28 - Jun 29

Quality Inn Great Barrington
Quality Inn Great Barrington10.3 km from Chesterwood
8.6 out of 10, Excellent, (1,003 reviews)
The price is ¥21,358
¥23,857 total
includes taxes & fees
Jul 1 - Jul 2

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, (780 reviews)
The price is ¥24,099
¥26,918 total
includes taxes & fees
Jul 5 - Jul 6

Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (380 reviews)
The price is ¥43,668
¥48,777 total
includes taxes & fees
Jun 30 - Jul 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, (788 reviews)
The price is ¥34,232
¥38,236 total
includes taxes & fees
Jul 16 - Jul 17

Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (587 reviews)
The price is ¥14,395
¥16,079 total
includes taxes & fees
Jun 29 - Jun 30

Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington7.4 km from Chesterwood
6.4 out of 10, (669 reviews)
The price is ¥14,985
¥16,738 total
includes taxes & fees
Jul 13 - Jul 14

Sunset Inn
Sunset Inn9.1 km from Chesterwood
7.6 out of 10, Good, (416 reviews)
The price is ¥16,012
¥17,886 total
includes taxes & fees
Jul 22 - Jul 23

Berkshires Untold
Berkshires Untold13 km from Chesterwood
9.0 out of 10, Wonderful, (991 reviews)
The price is ¥26,972
¥30,128 total
includes taxes & fees
Jun 29 - Jun 30

Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires12.5 km from Chesterwood
9.8 out of 10, Exceptional, (27 reviews)
The price is ¥32,833
¥36,675 total
includes taxes & fees
Jul 19 - Jul 20

The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,002 reviews)
The price is ¥34,237
¥39,390 total
includes taxes & fees
Jul 20 - Jul 21

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 ¥24,048
¥26,861 total
includes taxes & fees
Jul 7 - Jul 8

Berkshire Travel Lodge
Berkshire Travel Lodge9.7 km from Chesterwood
5.4 out of 10, (472 reviews)
The price is ¥10,916
¥12,226 total
includes taxes & fees
Jun 29 - Jun 30

The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (312 reviews)
The price is ¥25,067
¥28,000 total
includes taxes & fees
Jul 26 - Jul 27

Hideaway Inn Lenox
Hideaway Inn Lenox9.6 km from Chesterwood
7.8 out of 10, Good, (9 reviews)
The price is ¥25,587
¥28,581 total
includes taxes & fees
Jun 29 - Jun 30

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 ¥19,279
¥21,535 total
includes taxes & fees
Jun 30 - Jul 1

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG15.5 km from Chesterwood
9.4 out of 10, Exceptional, (116 reviews)
The price is ¥27,658
¥30,894 total
includes taxes & fees
Jul 6 - Jul 7

Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox14.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,003 reviews)
The price is ¥27,334
¥30,532 total
includes taxes & fees
Jun 29 - Jun 30

Little Cat Lodge
Little Cat Lodge16.3 km from Chesterwood
9.6 out of 10, Exceptional, (88 reviews)
The price is ¥24,601
¥27,553 total
includes taxes & fees
Jul 8 - Jul 9

Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox14.9 km from Chesterwood
7.6 out of 10, Good, (871 reviews)
The price is ¥14,395
¥16,079 total
includes taxes & fees
Jun 30 - Jul 1
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 | Star rating | Guest rating | Breakfast included | Pool | Spa | Pet friendly | WiFi included | |
|---|---|---|---|---|---|---|---|---|
![]() Pleasant Valley Motel West Stockbridge | 6.8 1,000 reviews | View | ||||||
![]() Quality Inn Great Barrington | 8.6 Excellent 1,003 reviews | View | ||||||
![]() Holiday Inn Express Hotel & Suites Great Barrington by IHG | 8.8 Excellent 780 reviews | View | ||||||
![]() Chambery Inn | 9.6 Exceptional 380 reviews | View | ||||||
![]() Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires | 9.4 Exceptional 788 reviews | View |
Top Chesterwood Hotel Reviews

Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay
10/10 Excellent








































































