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Our top choices for Chesterwood hotels

The Red Lion Inn
The Red Lion Inn2.1 mi from Chesterwood
8.8 out of 10, Excellent, (1,010 reviews)
The price is £151
includes taxes & fees
19 May - 20 May

Shaker Mill Inn
Shaker Mill Inn3.6 mi from Chesterwood
9.6 out of 10, Exceptional, (454 reviews)
The price is £98
includes taxes & fees
26 May - 27 May

The Little Lion
The Little Lion3.2 mi from Chesterwood
8.6 out of 10, Excellent, (559 reviews)
The price is £78
includes taxes & fees
11 Jun - 12 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 IHG4.1 mi from Chesterwood
9.2 out of 10, Wonderful, (894 reviews)
The price is £120
includes taxes & fees
18 May - 19 May

Monument Mountain Motel
Monument Mountain Motel5.4 mi from Chesterwood
9.0 out of 10, Wonderful, (852 reviews)
The price is £56
includes taxes & fees
21 May - 22 May

The Inn at Stockbridge
The Inn at Stockbridge3.2 mi from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
The price is £228
includes taxes & fees
25 May - 26 May

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG5 mi from Chesterwood
8.8 out of 10, Excellent, (764 reviews)
The price is £102
includes taxes & fees
27 May - 28 May

The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel5.3 mi from Chesterwood
9.0 out of 10, Wonderful, (1,000 reviews)
The price is £105
includes taxes & fees
17 May - 18 May

Chambery Inn
Chambery Inn5.4 mi from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
The price is £141
includes taxes & fees
20 May - 21 May

Devonfield Inn B&B
Devonfield Inn B&B4.7 mi from Chesterwood
10.0 out of 10, Exceptional, (138 reviews)
The price is £222
includes taxes & fees
18 May - 19 May

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires5.3 mi from Chesterwood
9.4 out of 10, Exceptional, (780 reviews)
The price is £161
includes taxes & fees
31 May - 1 Jun

Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires3.8 mi from Chesterwood
7.6 out of 10, Good, (578 reviews)
The price is £62
includes taxes & fees
26 May - 27 May

Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge2.9 mi from Chesterwood
6.8 out of 10, (1,000 reviews)
The price is £49
includes taxes & fees
26 May - 27 May

Quality Inn Great Barrington
Quality Inn Great Barrington6.4 mi from Chesterwood
8.4 out of 10, Very good, (1,000 reviews)
The price is £70
includes taxes & fees
17 May - 18 May

East Rock Inn
East Rock Inn6.3 mi from Chesterwood
9.4 out of 10, Exceptional, (44 reviews)
The price is £115
includes taxes & fees
18 May - 19 May

Brook Farm Inn
Brook Farm Inn5.7 mi from Chesterwood
9.4 out of 10, Exceptional, (164 reviews)
The price is £157
includes taxes & fees
3 Jun - 4 Jun

The Whitlock
The Whitlock6.1 mi from Chesterwood
8.6 out of 10, Excellent, (299 reviews)
The price is £95
includes taxes & fees
18 May - 19 May

Berkshires Untold
Berkshires Untold8.1 mi from Chesterwood
9.0 out of 10, Wonderful, (941 reviews)
The price is £83
includes taxes & fees
28 May - 29 May

Element Lenox Berkshires
Element Lenox Berkshires7.8 mi from Chesterwood
9.6 out of 10, Exceptional, (25 reviews)
The price is £131
includes taxes & fees
28 May - 29 May

Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington4.6 mi from Chesterwood
6.4 out of 10, (663 reviews)
The price is £53
includes taxes & fees
28 May - 29 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 Red Lion Inn | 8.8 Excellent 1,010 reviews | View | ||||||
![]() Shaker Mill Inn | 9.6 Exceptional 454 reviews | View | ||||||
![]() The Little Lion | 8.6 Excellent 559 reviews | View | ||||||
![]() Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG | 9.2 Wonderful 894 reviews | View | ||||||
![]() Monument Mountain Motel | 9.0 Wonderful 852 reviews | View |
Top Chesterwood Hotel Reviews

The Red Lion Inn
10/10 Excellent








































































