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Our top choices for Chesterwood hotels

The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
The price is CA $359
CA $421 total
includes taxes & fees
May 26 - May 27

Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (849 reviews)
The price is CA $93
CA $104 total
includes taxes & fees
May 17 - May 18

Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
The price is CA $234
CA $261 total
includes taxes & fees
May 10 - May 11

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, (760 reviews)
The price is CA $170
CA $189 total
includes taxes & fees
May 27 - May 28

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, (779 reviews)
The price is CA $243
CA $271 total
includes taxes & fees
May 20 - May 21

Quality Inn Great Barrington
Quality Inn Great Barrington10.3 km from Chesterwood
8.4 out of 10, Very good, (1,008 reviews)
The price is CA $116
CA $129 total
includes taxes & fees
May 12 - May 13

Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (578 reviews)
The price is CA $102
CA $114 total
includes taxes & fees
May 11 - May 12

The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,005 reviews)
The price is CA $135
CA $151 total
includes taxes & fees
May 17 - May 18

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 CA $182
CA $210 total
includes taxes & fees
May 10 - May 11

Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington7.4 km from Chesterwood
6.4 out of 10, (663 reviews)
The price is CA $87
CA $97 total
includes taxes & fees
May 25 - May 26

Sunset Inn
Sunset Inn9.1 km from Chesterwood
7.6 out of 10, Good, (412 reviews)
The price is CA $144
CA $161 total
includes taxes & fees
Jun 2 - Jun 3

Berkshire Travel Lodge
Berkshire Travel Lodge9.7 km from Chesterwood
5.4 out of 10, (466 reviews)
The price is CA $90
CA $101 total
includes taxes & fees
May 11 - May 12

The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (295 reviews)
The price is CA $157
CA $175 total
includes taxes & fees
May 12 - May 13

Element Lenox Berkshires
Element Lenox Berkshires12.5 km from Chesterwood
9.6 out of 10, Exceptional, (25 reviews)
The price is CA $228
CA $255 total
includes taxes & fees
May 25 - May 26

Inn at Kenmore Hall
Inn at Kenmore Hall12.1 km from Chesterwood
10.0 out of 10, Exceptional, (28 reviews)
The price is CA $581
CA $638 total
includes taxes & fees
May 10 - May 11

Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
8.4 out of 10, Very good, (1,004 reviews)
The price is CA $150
CA $168 total
includes taxes & fees
May 19 - May 20

Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox14.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,008 reviews)
The price is CA $187
CA $209 total
includes taxes & fees
May 17 - May 18

Prospect Berkshires
Prospect Berkshires12.8 km from Chesterwood
9.8 out of 10, Exceptional, (25 reviews)
The price is CA $449
CA $548 total
includes taxes & fees
May 11 - May 12

Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites16.9 km from Chesterwood
8.6 out of 10, Excellent, (1,001 reviews)
The price is CA $150
CA $168 total
includes taxes & fees
May 14 - May 15

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG15.5 km from Chesterwood
9.2 out of 10, Wonderful, (92 reviews)
The price is CA $161
CA $180 total
includes taxes & fees
May 17 - May 18
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 | |
|---|---|---|---|---|---|---|---|---|
![]() The Inn at Stockbridge | 9.8 Exceptional 99 reviews | View | ||||||
![]() Monument Mountain Motel | 9.0 Wonderful 849 reviews | View | ||||||
![]() Chambery Inn | 9.6 Exceptional 376 reviews | View | ||||||
![]() Holiday Inn Express Hotel & Suites Great Barrington by IHG | 8.8 Excellent 760 reviews | View | ||||||
![]() Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires | 9.4 Exceptional 779 reviews | View |
Top Chesterwood Hotel Reviews

The Red Lion Inn
10/10 Excellent
Hotels near other Chesterwood attractions
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