
Hotels near Chesterwood
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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 S$391
includes taxes & fees
21 May - 22 May

Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
The price is S$242
includes taxes & fees
10 May - 11 May

Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (849 reviews)
The price is S$97
includes taxes & fees
14 May - 15 May

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 S$176
includes taxes & fees
27 May - 28 May

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 S$251
includes taxes & fees
14 May - 15 May

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 S$120
includes taxes & fees
13 May - 14 May

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 S$106
includes taxes & fees
10 May - 11 May

The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,005 reviews)
The price is S$140
includes taxes & fees
20 May - 21 May

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 S$220
includes taxes & fees
13 May - 14 May

Sunset Inn
Sunset Inn9.1 km from Chesterwood
7.6 out of 10, Good, (412 reviews)
The price is S$149
includes taxes & fees
31 May - 1 Jun

Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington7.4 km from Chesterwood
6.4 out of 10, (663 reviews)
The price is S$90
includes taxes & fees
25 May - 26 May

Element Lenox Berkshires
Element Lenox Berkshires12.5 km from Chesterwood
9.6 out of 10, Exceptional, (25 reviews)
The price is S$236
includes taxes & fees
27 May - 28 May

Berkshire Travel Lodge
Berkshire Travel Lodge9.7 km from Chesterwood
5.4 out of 10, (466 reviews)
The price is S$93
includes taxes & fees
10 May - 11 May

The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (295 reviews)
The price is S$163
includes taxes & fees
11 May - 12 May

Inn at Kenmore Hall
Inn at Kenmore Hall12.1 km from Chesterwood
10.0 out of 10, Exceptional, (28 reviews)
The price is S$591
includes taxes & fees
10 May - 11 May

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 S$156
includes taxes & fees
19 May - 20 May

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 S$194
includes taxes & fees
17 May - 18 May

Prospect Berkshires
Prospect Berkshires12.8 km from Chesterwood
9.8 out of 10, Exceptional, (25 reviews)
The price is S$489
includes taxes & fees
10 May - 11 May

Whistler's Inn Bed & Breakfast
Whistler's Inn Bed & Breakfast10.4 km from Chesterwood
8.0 out of 10, Very good, (501 reviews)
The price is S$362
includes taxes & fees
31 May - 1 Jun

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 S$167
includes taxes & fees
17 May - 18 May
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 Inn at Stockbridge | 9.8 Exceptional 99 reviews | View | ||||||
![]() Chambery Inn | 9.6 Exceptional 376 reviews | View | ||||||
![]() Monument Mountain Motel | 9.0 Wonderful 849 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





































































