
Top Hotels Near Chesterwood in South Lee from NZ$110
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Our top choices for Chesterwood hotels

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 NZ$642
includes taxes & fees
5 Apr - 6 Apr

Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (446 reviews)
The price is NZ$189
includes taxes & fees
23 Mar - 24 Mar

Granville House
Granville House6.4 km from Chesterwood
10.0 out of 10, Exceptional, (97 reviews)
The price is NZ$333
includes taxes & fees
23 Mar - 24 Mar

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, (746 reviews)
The price is NZ$205
includes taxes & fees
30 Mar - 31 Mar

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 IHG6.6 km from Chesterwood
9.0 out of 10, Wonderful, (855 reviews)
The price is NZ$249
includes taxes & fees
24 Mar - 25 Mar

The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (555 reviews)
The price is NZ$211
includes taxes & fees
23 Mar - 24 Mar

The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel8.6 km from Chesterwood
9.2 out of 10, Wonderful, (1,001 reviews)
The price is NZ$182
includes taxes & fees
6 Apr - 7 Apr

Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (834 reviews)

The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
The price is NZ$480
includes taxes & fees
27 Mar - 28 Mar

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, (774 reviews)
The price is NZ$291
includes taxes & fees
29 Mar - 30 Mar

Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
10.0 out of 10, Exceptional, (136 reviews)

Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
8.4 out of 10, Very good, (1,000 reviews)
The price is NZ$161
includes taxes & fees
6 Apr - 7 Apr

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 NZ$144
includes taxes & fees
23 Mar - 24 Mar

Element Lenox Berkshires
Element Lenox Berkshires12.5 km from Chesterwood
9.8 out of 10, Exceptional, (23 reviews)
The price is NZ$266
includes taxes & fees
29 Mar - 30 Mar

East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.4 out of 10, Exceptional, (40 reviews)
The price is NZ$229
includes taxes & fees
5 Apr - 6 Apr

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 NZ$110
includes taxes & fees
24 Mar - 25 Mar

Berkshires Untold
Berkshires Untold13 km from Chesterwood
9.0 out of 10, Wonderful, (879 reviews)
The price is NZ$134
includes taxes & fees
1 Apr - 2 Apr
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 | ||||||
![]() The Red Lion Inn | 8.8 Excellent 1,000 reviews | View | ||||||
![]() Shaker Mill Inn | 9.6 Exceptional 446 reviews | View | ||||||
![]() Granville House | 10.0 Exceptional 97 reviews | View | ||||||
![]() Holiday Inn Express Hotel & Suites Great Barrington by IHG | 8.8 Excellent 746 reviews | View |
Top Chesterwood Hotel Reviews

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10/10 Excellent











































































