
Find hotels near Chesterwood, South Lee from CA $125
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
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, (774 reviews)
The price is CA $211
CA $236 total
includes taxes & fees
Jun 23 - Jun 24

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, (787 reviews)
The price is CA $281
CA $314 total
includes taxes & fees
Jun 24 - Jun 25

3. Quality Inn Great Barrington
Quality Inn Great Barrington10.3 km from Chesterwood
8.6 out of 10, Excellent, (1,008 reviews)
The price is CA $147
CA $164 total
includes taxes & fees
Jun 23 - Jun 24

4. Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (378 reviews)
The price is CA $382
CA $427 total
includes taxes & fees
Jul 1 - Jul 2

5. Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (585 reviews)
The price is CA $112
CA $125 total
includes taxes & fees
Jun 22 - Jun 23

6. Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington7.4 km from Chesterwood
6.4 out of 10, (668 reviews)
The price is CA $112
CA $125 total
includes taxes & fees
Jun 22 - Jun 23

7. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires12.5 km from Chesterwood
9.8 out of 10, Exceptional, (26 reviews)
The price is CA $287
CA $320 total
includes taxes & fees
Jul 19 - Jul 20

8. Berkshires Untold
Berkshires Untold13 km from Chesterwood
9.0 out of 10, Wonderful, (990 reviews)
The price is CA $203
CA $227 total
includes taxes & fees
Jun 22 - Jun 23

9. The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (310 reviews)
The price is CA $219
CA $245 total
includes taxes & fees
Jul 6 - Jul 7

10. The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,002 reviews)
The price is CA $217
CA $250 total
includes taxes & fees
Jun 25 - Jun 26

11. Hideaway Inn Lenox
Hideaway Inn Lenox9.6 km from Chesterwood
7.6 out of 10, Good, (8 reviews)
The price is CA $224
CA $250 total
includes taxes & fees
Jul 5 - Jul 6

12. Little Cat Lodge
Little Cat Lodge16.3 km from Chesterwood
9.6 out of 10, Exceptional, (84 reviews)
The price is CA $215
CA $241 total
includes taxes & fees
Jun 28 - Jun 29

13. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
8.4 out of 10, Very good, (1,002 reviews)
The price is CA $211
CA $236 total
includes taxes & fees
Jun 22 - Jun 23

14. 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, (108 reviews)
The price is CA $198
CA $221 total
includes taxes & fees
Jun 29 - Jun 30

15. Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield15.5 km from Chesterwood
9.2 out of 10, Wonderful, (682 reviews)
The price is CA $212
CA $236 total
includes taxes & fees
Jun 24 - Jun 25

16. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites16.9 km from Chesterwood
8.6 out of 10, Excellent, (1,000 reviews)
The price is CA $157
CA $176 total
includes taxes & fees
Jun 23 - Jun 24

17. The Central Downtown Inn & Suites
The Central Downtown Inn & Suites19.6 km from Chesterwood
8.6 out of 10, Excellent, (370 reviews)
The price is CA $161
CA $180 total
includes taxes & fees
Jun 22 - Jun 23

18. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG19.8 km from Chesterwood
8.0 out of 10, Very good, (1,002 reviews)
The price is CA $180
CA $201 total
includes taxes & fees
Jun 29 - Jun 30
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 774 reviews | View | ||||||
![]() Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires | 9.4 Exceptional 787 reviews | View | ||||||
![]() Quality Inn Great Barrington | 8.6 Excellent 1,008 reviews | View | ||||||
![]() Chambery Inn | 9.6 Exceptional 378 reviews | View | ||||||
![]() Travelodge by Wyndham Great Barrington Berkshires | 7.6 Good 585 reviews | View |
Top Chesterwood Hotel Reviews

The Red Lion Inn
10/10 Excellent
Hotels near other Chesterwood attractions
Frequently asked questions
Explore a world of travel with Expedia
- 3 Star Hotels in Stockbridge
- Guest Houses in Alford
- Alford Hotels
- Lodges in Alford
- Hotels near Berkshire Botanical Garden
- Berkshire County Hotels
- Farmstay in Glendale
- Apartments in Glendale
- Resorts in Glendale
- Great Barrington Hotels
- Hotels near Hancock Shaker Village
- Housatonic Hotels
- Hotels near Jacob's Pillow
- B&B in Lee
- Chalets in Lee
- Guest Houses in Lee
- Cheap Hotels in Lee
- Luxury Hotels in Lee
- Pet-Friendly Hotels in Lee
- Spa Hotels in Lee
- Lee Hotels
- Inns in Lee
- Motels in Lee
- Hotels near Lee Premium Outlets
- Aparthotels in Lenox
- B&B in Lenox
- Chalets in Lenox
- Guest Houses in Lenox
- Holiday Park Resorts in Lenox
- Adults Only Resorts & in Lenox
- Beach Hotel Hotels in Lenox
- Boutique Hotels in Lenox
- Cheap Hotels in Lenox
- Honeymoon Resorts and in Lenox
- Hotels with an Indoor Pool in Lenox
- Lgbt Friendly Hotels in Lenox
- Luxury Hotels in Lenox
- Spa Hotels in Lenox
- Lenox Hotels
- Inns in Lenox
- Resorts in Lenox
- Hotels near Mahaiwe Performing Arts Center
- Mill River Hotels
- Monterey Hotels
- Hotels near National Shrine of the Divine Mercy
- New Marlborough Hotels
- Hotels near Norman Rockwell Museum
- Pittsfield Hotels
- Richmond Hotels
- Sheffield Hotels
- Hotels near Ski Butternut
- South Egremont Hotels
- Guest Houses in South Lee
- Cheap Hotels in South Lee
- Hotels & Resorts for Couples in South Lee
- Family Hotels in South Lee
- Luxury Hotels in South Lee
- Pet-Friendly Hotels in South Lee
- Romantic Hotels in South Lee
- Spa Hotels in South Lee
- South Lee Hotels
- Resorts in South Lee
- Townhomes in South Lee
- B&B in Stockbridge
- Guest Houses in Stockbridge
- Boutique Hotels in Stockbridge
- Cheap Hotels in Stockbridge
- Historic Hotels in Stockbridge
- Luxury Hotels in Stockbridge
- Pet-Friendly Hotels in Stockbridge
- Stockbridge Hotels
- Resorts in Stockbridge
- Hotels near Tanglewood Music Center
- The Berkshires Hotels
- Hotels near The Mount
- Hotels near Tyringham Cobble
- Tyringham Hotels
- Hotels near Ventfort Hall Mansion and Gilded Age Museum
- Lgbt Friendly Hotels in West Stockbridge
- Luxury Hotels in West Stockbridge
- Pet-Friendly Hotels in West Stockbridge
- Spa Hotels in West Stockbridge
- West Stockbridge Hotels


































































