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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 12 - Aug 13
Total with taxes and fees

2. Monument Mountain Motel
Monument Mountain Motel5.4 mi from Chesterwood
9.0 out of 10, Wonderful, (888 reviews)
$124 nightly
The price is $138
Jul 29 - Jul 30
Total with taxes and fees

3. Quality Inn Great Barrington
Quality Inn Great Barrington6.4 mi from Chesterwood
8.6 out of 10, Excellent, (1,004 reviews)
$118 nightly
The price is $132
Aug 18 - Aug 19
Total with taxes and fees

4. East Rock Inn
East Rock Inn6.3 mi from Chesterwood
9.6 out of 10, Exceptional, (51 reviews)
$151 nightly
The price is $168
Aug 26 - Aug 27
Total with taxes and fees

5. The Little Lion
The Little Lion3.2 mi from Chesterwood
8.6 out of 10, Excellent, (594 reviews)
$125 nightly
The price is $139
Aug 3 - Aug 4
Total with taxes and fees

6. Berkshire Mountain Lodge
Berkshire Mountain Lodge9.9 mi from Chesterwood
9.0 out of 10, Wonderful, (1,029 reviews)
$142 nightly
The price is $158
Aug 26 - Aug 27
Total with taxes and fees

7. 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, (795 reviews)
$140 nightly
The price is $156
Aug 23 - Aug 24
Total with taxes and fees

8. Wilder House Berkshires
Wilder House Berkshires12.4 mi from Chesterwood
9.8 out of 10, Exceptional, (59 reviews)
$195 nightly
The price is $218
Aug 10 - Aug 11
Total with taxes and fees

9. Berkshire Lake Lodge
Berkshire Lake Lodge10 mi from Chesterwood
9.6 out of 10, Exceptional, (8 reviews)
$161 nightly
The price is $179
Aug 3 - Aug 4
Total with taxes and fees

10. Little Cat Lodge
Little Cat Lodge10.1 mi from Chesterwood
9.6 out of 10, Exceptional, (109 reviews)
$199 nightly
The price is $223
Jul 29 - Jul 30
Total with taxes and fees

11. The Inn at Stockbridge
The Inn at Stockbridge3.2 mi from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
$389 nightly
The price is $435
Jul 29 - Jul 30
Total with taxes and fees

12. 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, (798 reviews)
$195 nightly
The price is $217
Aug 10 - Aug 11
Total with taxes and fees

13. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South5.7 mi from Chesterwood
8.4 out of 10, Very Good, (1,009 reviews)
$127 nightly
The price is $142
Aug 24 - Aug 25
Total with taxes and fees

14. Chambery Inn
Chambery Inn5.4 mi from Chesterwood
9.6 out of 10, Exceptional, (383 reviews)
$300 nightly
The price is $335
Aug 2 - Aug 3
Total with taxes and fees

15. The Yankee Inn
The Yankee Inn9.3 mi from Chesterwood
9.2 out of 10, Wonderful, (1,027 reviews)
$158 nightly
The price is $176
Jul 30 - Jul 31
Total with taxes and fees

16. The Central Downtown Inn & Suites
The Central Downtown Inn & Suites12.2 mi from Chesterwood
8.6 out of 10, Excellent, (381 reviews)
$104 nightly
The price is $116
Jul 29 - Jul 30
Total with taxes and fees

17. 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, (145 reviews)
$145 nightly
The price is $162
Aug 2 - Aug 3
Total with taxes and fees

18. Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires3.8 mi from Chesterwood
7.4 out of 10, Good, (599 reviews)
$99 nightly
The price is $111
Aug 2 - Aug 3
Total with taxes and fees

19. Inn at Silver Maple Farm
Inn at Silver Maple Farm10.8 mi from Chesterwood
9.8 out of 10, Exceptional, (112 reviews)
$229 nightly
The price is $256
Aug 24 - Aug 25
Total with taxes and fees

20. Prospect Berkshires
Prospect Berkshires7.9 mi from Chesterwood
9.8 out of 10, Exceptional, (38 reviews)
$445 nightly
The price is $497
Jul 29 - Jul 30
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 | ||||||
![]() Monument Mountain Motel | 9.0 Wonderful 888 reviews | View | ||||||
![]() Quality Inn Great Barrington | 8.6 Excellent 1,004 reviews | View | ||||||
![]() East Rock Inn | 9.6 Exceptional 51 reviews | View | ||||||
![]() The Little Lion | 8.6 Excellent 594 reviews | View |
Top Chesterwood Hotel Reviews

Hearth House | Prime Location!
10/10 Excellent
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