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Our top choices for Chesterwood hotels

1. 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
9.2 out of 10, Wonderful, (904 reviews)
The price is ₹12,732
₹16,078 total
includes taxes & fees
9 Jun - 10 Jun

2. Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge4.7 km from Chesterwood
6.8 out of 10, (1,002 reviews)
The price is ₹5,955
₹6,532 total
includes taxes & fees
18 Jun - 19 Jun

3. 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, (784 reviews)
The price is ₹18,481
₹20,643 total
includes taxes & fees
29 Jun - 30 Jun

4. Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (582 reviews)
The price is ₹7,500
₹8,378 total
includes taxes & fees
7 Jun - 8 Jun

5. 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, (769 reviews)
The price is ₹13,387
₹14,953 total
includes taxes & fees
21 Jun - 22 Jun

6. Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington7.4 km from Chesterwood
6.4 out of 10, (666 reviews)
The price is ₹6,750
₹7,540 total
includes taxes & fees
14 Jun - 15 Jun

7. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
8.4 out of 10, Very good, (1,003 reviews)
The price is ₹11,635
₹12,997 total
includes taxes & fees
9 Jun - 10 Jun

8. Berkshire Travel Lodge
Berkshire Travel Lodge9.7 km from Chesterwood
5.4 out of 10, (468 reviews)
The price is ₹6,237
₹6,986 total
includes taxes & fees
7 Jun - 8 Jun

9. Sunset Inn
Sunset Inn9.1 km from Chesterwood
7.6 out of 10, Good, (413 reviews)
The price is ₹9,922
₹11,082 total
includes taxes & fees
8 Jun - 9 Jun

10. The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,001 reviews)
The price is ₹14,466
₹16,643 total
includes taxes & fees
7 Jun - 8 Jun

11. Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (377 reviews)
The price is ₹16,234
₹18,134 total
includes taxes & fees
7 Jun - 8 Jun

12. The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (305 reviews)
The price is ₹14,714
₹16,436 total
includes taxes & fees
21 Jun - 22 Jun

13. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires12.1 km from Chesterwood
9.2 out of 10, Wonderful, (629 reviews)
The price is ₹18,713
₹20,903 total
includes taxes & fees
11 Jun - 12 Jun

14. Hideaway Inn Lenox
Hideaway Inn Lenox9.6 km from Chesterwood
8.6 out of 10, Excellent, (4 reviews)
The price is ₹9,801
₹10,948 total
includes taxes & fees
7 Jun - 8 Jun

15. 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, (100 reviews)
The price is ₹12,817
₹14,317 total
includes taxes & fees
14 Jun - 15 Jun

16. Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield15.5 km from Chesterwood
9.2 out of 10, Wonderful, (679 reviews)
The price is ₹13,888
₹15,514 total
includes taxes & fees
14 Jun - 15 Jun

17. Little Cat Lodge
Little Cat Lodge16.3 km from Chesterwood
9.6 out of 10, Exceptional, (79 reviews)
The price is ₹14,441
₹16,174 total
includes taxes & fees
8 Jun - 9 Jun

18. 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 ₹10,558
₹11,793 total
includes taxes & fees
10 Jun - 11 Jun

19. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox14.9 km from Chesterwood
7.6 out of 10, Good, (863 reviews)
The price is ₹7,500
₹8,378 total
includes taxes & fees
8 Jun - 9 Jun

20. The Central Downtown Inn & Suites
The Central Downtown Inn & Suites19.6 km from Chesterwood
8.6 out of 10, Excellent, (368 reviews)
The price is ₹10,823
₹12,090 total
includes taxes & fees
7 Jun - 8 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 | |
|---|---|---|---|---|---|---|---|---|
![]() Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG | 9.2 Wonderful 904 reviews | View | ||||||
![]() Pleasant Valley Motel West Stockbridge | 6.8 1,002 reviews | View | ||||||
![]() Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires | 9.4 Exceptional 784 reviews | View | ||||||
![]() Travelodge by Wyndham Great Barrington Berkshires | 7.6 Good 582 reviews | View | ||||||
![]() Holiday Inn Express Hotel & Suites Great Barrington by IHG | 8.8 Excellent 769 reviews | View |
Top Chesterwood Hotel Reviews

The Little Lion
10/10 Excellent
Hotels near other Chesterwood attractions
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