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Our top choices for Chesterwood hotels

1. 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 Chesterwood0.4 mi from Chesterwood
9.2 out of 10, Wonderful, (113 reviews)
$358 nightly
The price is $399
Aug 3 - Aug 4
Total with taxes and fees

2. 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, (792 reviews)
$137 nightly
The price is $153
Aug 13 - Aug 14
Total with taxes and fees

3. The Red Lion Inn
The Red Lion Inn2.1 mi from Chesterwood
8.8 out of 10, Excellent, (1,005 reviews)
$223 nightly
The price is $249
Jul 29 - Jul 30
Total with taxes and fees

4. Monument Mountain Motel
Monument Mountain Motel5.4 mi from Chesterwood
9.0 out of 10, Wonderful, (885 reviews)
$124 nightly
The price is $138
Jul 23 - Jul 24
Total with taxes and fees

5. 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, (940 reviews)
$167 nightly
The price is $186
Jul 29 - Jul 30
Total with taxes and fees

6. The Yankee Inn
The Yankee Inn9.3 mi from Chesterwood
9.2 out of 10, Wonderful, (1,008 reviews)
$169 nightly
The price is $189
Jul 22 - Jul 23
Total with taxes and fees

7. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South5.7 mi from Chesterwood
8.4 out of 10, Very Good, (1,000 reviews)
$135 nightly
The price is $151
Aug 10 - Aug 11
Total with taxes and fees

8. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites10.5 mi from Chesterwood
8.6 out of 10, Excellent, (1,002 reviews)
$118 nightly
The price is $132
Jul 26 - Jul 27
Total with taxes and fees

9. Berkshire Lake Lodge
Berkshire Lake Lodge10 mi from Chesterwood
9.6 out of 10, Exceptional, (7 reviews)
$196 nightly
The price is $219
Jul 22 - Jul 23
Total with taxes and fees

10. East Rock Inn
East Rock Inn6.3 mi from Chesterwood
9.6 out of 10, Exceptional, (51 reviews)
$156 nightly
The price is $174
Aug 19 - Aug 20
Total with taxes and fees

11. The Little Lion
The Little Lion3.2 mi from Chesterwood
8.6 out of 10, Excellent, (587 reviews)
$137 nightly
The price is $152
Jul 26 - Jul 27
Total with taxes and fees

12. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG9.6 mi from Chesterwood
9.4 out of 10, Exceptional, (137 reviews)
$145 nightly
The price is $162
Jul 26 - Jul 27
Total with taxes and fees

13. Berkshires Untold
Berkshires Untold8.1 mi from Chesterwood
9.0 out of 10, Wonderful, (1,005 reviews)
$165 nightly
The price is $184
Jul 23 - Jul 24
Total with taxes and fees

14. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires7.8 mi from Chesterwood
9.8 out of 10, Exceptional, (28 reviews)
$229 nightly
The price is $256
Jul 24 - Jul 25
Total with taxes and fees

15. Granville House
Granville House4 mi from Chesterwood
10.0 out of 10, Exceptional, (102 reviews)
$225 nightly
The price is $251
Jul 29 - Jul 30
Total with taxes and fees

16. Devonfield Inn B&B
Devonfield Inn B&B4.7 mi from Chesterwood
10.0 out of 10, Exceptional, (139 reviews)
$439 nightly
The price is $490
Jul 21 - Jul 22
Total with taxes and fees

17. Quality Inn Great Barrington
Quality Inn Great Barrington6.4 mi from Chesterwood
8.6 out of 10, Excellent, (1,005 reviews)
$118 nightly
The price is $132
Aug 10 - Aug 11
Total with taxes and fees

18. Chambery Inn
Chambery Inn5.4 mi from Chesterwood
9.6 out of 10, Exceptional, (381 reviews)
$293 nightly
The price is $328
Jul 26 - Jul 27
Total with taxes and fees

19. The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires6.7 mi from Chesterwood
9.2 out of 10, Wonderful, (1,002 reviews)
$168 nightly
The price is $188
Jul 26 - Jul 27
Total with taxes and fees

20. Berkshire Mountain Lodge
Berkshire Mountain Lodge9.9 mi from Chesterwood
9.0 out of 10, Wonderful, (1,015 reviews)
$155 nightly
The price is $173
Aug 19 - Aug 20
Total with taxes and fees
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 Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood | 9.2 Wonderful 113 reviews | View | ||||||
![]() Holiday Inn Express Hotel & Suites Great Barrington by IHG | 8.8 Excellent 792 reviews | View | ||||||
![]() The Red Lion Inn | 8.8 Excellent 1,005 reviews | View | ||||||
![]() Monument Mountain Motel | 9.0 Wonderful 885 reviews | View | ||||||
![]() Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG | 9.2 Wonderful 940 reviews | View |
Top Chesterwood Hotel Reviews

The Red Lion Inn
8/10 Good
Hotels near other Chesterwood attractions
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