Find hotels near Chesterwood, South Lee from ₩153,601
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Aug 21 - Aug 22Tomorrow
Aug 22 - Aug 23This weekend
Aug 21 - Aug 23Next weekend
Aug 28 - Aug 30 Our top choices for Chesterwood hotels
1. Berkshire Mountain Lodge
Berkshire Mountain Lodge15.9 km from Chesterwood
Robert
₩131,394
₩177,797 total
includes taxes & fees
Aug 31 - Sep 1
2. Berkshire Lake Lodge
Berkshire Lake Lodge16.2 km from Chesterwood
mike
₩206,614
₩230,787 total
includes taxes & fees
Aug 31 - Sep 1
3. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel8.6 km from Chesterwood
James
₩177,098
₩197,818 total
includes taxes & fees
Sep 14 - Sep 15
4. The Little Lion
The Little Lion5.1 km from Chesterwood
Anne
₩156,262
₩174,545 total
includes taxes & fees
Sep 2 - Sep 3
5. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG8 km from Chesterwood
BJORN
₩160,368
₩179,131 total
includes taxes & fees
Sep 20 - Sep 21
6. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
Christine
₩152,304
₩170,123 total
includes taxes & fees
Sep 15 - Sep 16
7. The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
Karen
₩219,462
₩245,139 total
includes taxes & fees
Sep 14 - Sep 15
8. East Rock Inn
East Rock Inn10.1 km from Chesterwood
ERIK
₩175,041
₩195,520 total
includes taxes & fees
Sep 14 - Sep 15
9. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires8.6 km from Chesterwood
Lisa
₩270,369
₩302,002 total
includes taxes & fees
Aug 25 - Aug 26
10. Chambery Inn
Chambery Inn8.7 km from Chesterwood
Richard
₩376,501
₩420,553 total
includes taxes & fees
Sep 20 - Sep 21
11. Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield15.5 km from Chesterwood
James
₩203,987
₩227,853 total
includes taxes & fees
Sep 13 - Sep 14
12. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires12.5 km from Chesterwood
Lawrence
₩258,354
₩288,581 total
includes taxes & fees
Aug 31 - Sep 1
13. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires12.1 km from Chesterwood
Laura
₩246,756
₩275,627 total
includes taxes & fees
Sep 7 - Sep 8
14. Berkshires Untold
Berkshires Untold13 km from Chesterwood
Pamela
₩177,512
₩198,282 total
includes taxes & fees
Sep 9 - Sep 10
15. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG15.5 km from Chesterwood
Ken
₩176,403
₩197,044 total
includes taxes & fees
Sep 14 - Sep 15
16. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites16.9 km from Chesterwood
Jermaine
₩158,318
₩176,841 total
includes taxes & fees
Sep 1 - Sep 2
17. The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
Michele
₩525,699
₩616,578 total
includes taxes & fees
Sep 13 - Sep 14
18. Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
Mervin
₩251,409
₩275,795 total
includes taxes & fees
Sep 8 - Sep 9
19. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox14.7 km from Chesterwood
Nancy
₩181,704
₩202,965 total
includes taxes & fees
Sep 20 - Sep 21
20. Sunset Inn
Sunset Inn9.1 km from Chesterwood
Kevin
₩137,511
₩153,601 total
includes taxes & fees
Sep 1 - Sep 2
Top Chesterwood Hotel Reviews
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
10/10 Excellent
"My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty of towels, and a generous selection of bath amenities that made settling in effortless. Breakfast was a standout: a truly amazing cook‑to‑order meal that felt both homemade and high‑end. Every dish was fresh, delicious, and clearly prepared with pride. Parking was plentiful and convenient, making arrival and departure stress‑free. Overall, this B&B is a gem — comfortable, inviting, and thoughtfully run. I’d happily return and recommend it to anyone looking for a relaxing stay."
The Little Lion
10/10 Excellent
"Clean, convenient, remotely operated by the owner, the Red Lion, a short distance away. We could use all the amenities offered by the Red Lion (meals, pool, hot tub) while staying at the much more reasonable Little Lion. A great bargain for Stockbridge!"
Pleasant Valley Motel West Stockbridge
8/10 Good
"It was good place to stay over night for our plan. Friendly staff and clean room. Deer family are living near by, enjoy viewing them. It’s a old building, but nice quiet place."
Other attractions near Chesterwood
Norman Rockwell Museum
9.4/10 (347 reviews)
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.
Berkshire Botanical Garden
9.4/10 (14 reviews)
Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.
Mission House
9.6/10 (5 reviews)
You can spend time exploring the galleries in Mission House in Stockbridge. Wander the lakeside in this quaint area.
Naumkeag Museum
9.4/10 (10 reviews)
You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside.
National Shrine of the Divine Mercy
9.0/10 (83 reviews)
Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.
Schantz Galleries
7.2/10 (5 reviews)
You can spend an afternoon exploring the galleries in Schantz Galleries during your trip to Stockbridge. Wander the lakeside in this quaint area.
Art et Industrie
8.0/10 (5 reviews)
You can spend an afternoon exploring the galleries in Art et Industrie in Great Barrington. Amble around this quaint area's gardens, or seek out the hiking trails.
Berkshire Theatre Festival
8.8/10 (3 reviews)
You can get tickets for a performance at Berkshire Theatre Festival on your trip to Stockbridge. Wander the lakeside in this quaint area.