
Find hotels near Chesterwood, South Lee from CA $93
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Our top choices for Chesterwood hotels

1. 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, (853 reviews)
The price is CA $116
CA $130 total
includes taxes & fees
Dec 2 - Dec 3

2. 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, (820 reviews)
The price is CA $224
CA $251 total
includes taxes & fees
Nov 8 - Nov 9

3. Quality Inn Great Barrington
Quality Inn Great Barrington10.3 km from Chesterwood
8.6 out of 10, Excellent, (1,003 reviews)
The price is CA $106
CA $118 total
includes taxes & fees
Nov 25 - Nov 26

4. 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, (1,005 reviews)
The price is CA $152
CA $170 total
includes taxes & fees
Nov 15 - Nov 16

5. Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
8.8 out of 10, Excellent, (938 reviews)
The price is CA $84
CA $93 total
includes taxes & fees
Nov 4 - Nov 5

6. The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,010 reviews)
The price is CA $145
CA $161 total
includes taxes & fees
Nov 20 - Nov 21

7. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires12.1 km from Chesterwood
9.2 out of 10, Wonderful, (683 reviews)
The price is CA $159
CA $178 total
includes taxes & fees
Nov 29 - Nov 30

8. Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (483 reviews)
The price is CA $203
CA $222 total
includes taxes & fees
Nov 4 - Nov 5

9. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox14.7 km from Chesterwood
9.0 out of 10, Wonderful, (1,001 reviews)
The price is CA $153
CA $171 total
includes taxes & fees
Nov 9 - Nov 10

10. East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.6 out of 10, Exceptional, (58 reviews)
The price is CA $179
CA $199 total
includes taxes & fees
Dec 4 - Dec 5

11. The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,004 reviews)
The price is CA $220
CA $315 total
includes taxes & fees
Nov 8 - Nov 9

12. Berkshires Untold
Berkshires Untold13 km from Chesterwood
9.0 out of 10, Wonderful, (1,063 reviews)
The price is CA $170
CA $190 total
includes taxes & fees
Nov 29 - Nov 30

13. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
8.6 out of 10, Excellent, (1,002 reviews)
The price is CA $118
CA $132 total
includes taxes & fees
Dec 2 - Dec 3

14. Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield15.5 km from Chesterwood
9.2 out of 10, Wonderful, (716 reviews)
The price is CA $166
CA $185 total
includes taxes & fees
Nov 22 - Nov 23

15. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites16.9 km from Chesterwood
8.4 out of 10, Very good, (1,000 reviews)
The price is CA $131
CA $146 total
includes taxes & fees
Dec 2 - Dec 3

16. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires6.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,002 reviews)
The price is CA $155
CA $200 total
includes taxes & fees
Nov 5 - Nov 6

17. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires12.5 km from Chesterwood
9.6 out of 10, Exceptional, (51 reviews)
The price is CA $189
CA $211 total
includes taxes & fees
Nov 9 - Nov 10

18. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG15.5 km from Chesterwood
9.2 out of 10, Wonderful, (254 reviews)
The price is CA $144
CA $161 total
includes taxes & fees
Dec 2 - Dec 3

19. The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (637 reviews)
The price is CA $116
CA $129 total
includes taxes & fees
Nov 9 - Nov 10

20. Berkshire Mountain Lodge
Berkshire Mountain Lodge15.9 km from Chesterwood
9.0 out of 10, Wonderful, (1,253 reviews)
The price is CA $116
CA $160 total
includes taxes & fees
Nov 8 - Nov 9
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 | |
|---|---|---|---|---|---|---|---|---|
![]() Holiday Inn Express Hotel & Suites Great Barrington by IHG | 8.8 Excellent 853 reviews | View | ||||||
![]() Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires | 9.4 Exceptional 820 reviews | View | ||||||
![]() Quality Inn Great Barrington | 8.6 Excellent 1,003 reviews | View | ||||||
![]() The Black Swan Lee - Lenox, an Ascend Collection Hotel | 9.2 Wonderful 1,005 reviews | View | ||||||
![]() Monument Mountain Motel | 8.8 Excellent 938 reviews | View |
Hotels recommended for families near Chesterwood
The price is CA $116
CA $129 total
includes taxes & fees
Nov 9 - Nov 10
Top Chesterwood Hotel Reviews

The Red Lion Inn
8/10 Good
Other attractions near Chesterwood
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