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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, (111 reviews)
The price is Rp5.896.836
Rp7.133.461 total
includes taxes & fees
29 Jun - 30 Jun

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, (785 reviews)
The price is Rp3.476.449
Rp3.883.194 total
includes taxes & fees
1 Jul - 2 Jul

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, (772 reviews)
The price is Rp2.446.820
Rp2.733.116 total
includes taxes & fees
23 Jun - 24 Jun

The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,006 reviews)
The price is Rp2.743.296
Rp3.862.246 total
includes taxes & fees
22 Jun - 23 Jun

Quality Inn Great Barrington
Quality Inn Great Barrington10.3 km from Chesterwood
8.6 out of 10, Excellent, (1,001 reviews)
The price is Rp1.679.733
Rp1.876.193 total
includes taxes & fees
17 Jun - 18 Jun

East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.4 out of 10, Exceptional, (48 reviews)
The price is Rp2.592.736
Rp2.896.086 total
includes taxes & fees
13 Jul - 14 Jul

Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (583 reviews)
The price is Rp1.410.940
Rp1.576.020 total
includes taxes & fees
15 Jun - 16 Jun

Little Cat Lodge
Little Cat Lodge16.3 km from Chesterwood
9.6 out of 10, Exceptional, (81 reviews)
The price is Rp2.716.506
Rp3.042.486 total
includes taxes & fees
21 Jun - 22 Jun

The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,013 reviews)
The price is Rp1.871.728
Rp2.090.692 total
includes taxes & fees
15 Jun - 16 Jun

The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (307 reviews)
The price is Rp2.767.943
Rp3.091.792 total
includes taxes & fees
25 Jun - 26 Jun

Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington7.4 km from Chesterwood
6.4 out of 10, (666 reviews)
The price is Rp1.351.109
Rp1.509.189 total
includes taxes & fees
29 Jun - 30 Jun

Prospect Berkshires
Prospect Berkshires12.8 km from Chesterwood
9.8 out of 10, Exceptional, (29 reviews)
The price is Rp5.867.010
Rp7.151.858 total
includes taxes & fees
6 Jul - 7 Jul

Berkshire Travel Lodge
Berkshire Travel Lodge9.7 km from Chesterwood
5.4 out of 10, (469 reviews)
The price is Rp1.173.223
Rp1.314.139 total
includes taxes & fees
15 Jun - 16 Jun

The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,003 reviews)
The price is Rp2.980.477
Rp3.429.067 total
includes taxes & fees
16 Jun - 17 Jun

Berkshires Untold
Berkshires Untold13 km from Chesterwood
9.0 out of 10, Wonderful, (986 reviews)
The price is Rp2.430.353
Rp2.714.704 total
includes taxes & fees
15 Jun - 16 Jun

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 Rp2.057.472
Rp2.298.197 total
includes taxes & fees
16 Jun - 17 Jun

Inn at Silver Maple Farm
Inn at Silver Maple Farm17.5 km from Chesterwood
9.8 out of 10, Exceptional, (107 reviews)
The price is Rp2.839.740
Rp3.180.509 total
includes taxes & fees
17 Jun - 18 Jun

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, (106 reviews)
The price is Rp2.500.400
Rp2.792.947 total
includes taxes & fees
22 Jun - 23 Jun

Wilder House Berkshires
Wilder House Berkshires19.9 km from Chesterwood
9.8 out of 10, Exceptional, (53 reviews)
The price is Rp3.443.051
Rp3.845.972 total
includes taxes & fees
22 Jun - 23 Jun

Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox14.9 km from Chesterwood
7.6 out of 10, Good, (867 reviews)
The price is Rp1.410.940
Rp1.576.020 total
includes taxes & fees
15 Jun - 16 Jun
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 111 reviews | View | ||||||
![]() Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires | 9.4 Exceptional 785 reviews | View | ||||||
![]() Holiday Inn Express Hotel & Suites Great Barrington by IHG | 8.8 Excellent 772 reviews | View | ||||||
![]() The Red Lion Inn | 8.8 Excellent 1,006 reviews | View | ||||||
![]() Quality Inn Great Barrington | 8.6 Excellent 1,001 reviews | View |
Top Chesterwood Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
10/10 Excellent




































































