Find hotels near Chesterwood, South Lee from ₩105,353
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Aug 22 - Aug 23Tomorrow
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Aug 28 - Aug 30In two weeks
Sep 4 - Sep 6 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 Chesterwood0.6 km from Chesterwood
Philippe
₩457,559
₩553,513 total
includes taxes & fees
Sep 7 - Sep 8
2. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires8.6 km from Chesterwood
Lisa
₩269,752
₩301,313 total
includes taxes & fees
Sep 21 - Sep 22
3. Chambery Inn
Chambery Inn8.7 km from Chesterwood
Richard
₩374,160
₩417,938 total
includes taxes & fees
Sep 21 - Sep 22
4. The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
Karen
₩218,961
₩244,585 total
includes taxes & fees
Sep 21 - Sep 22
5. Berkshires Untold
Berkshires Untold13 km from Chesterwood
Pamela
₩178,216
₩199,068 total
includes taxes & fees
Sep 9 - Sep 10
6. Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
Mervin
₩248,221
₩272,299 total
includes taxes & fees
Sep 8 - Sep 9
7. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
Christine
₩151,956
₩169,734 total
includes taxes & fees
Sep 22 - Sep 23
8. 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
9. Sunset Inn
Sunset Inn9.1 km from Chesterwood
Kevin
₩134,703
₩150,463 total
includes taxes & fees
Sep 22 - Sep 23
10. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires12.1 km from Chesterwood
Laura
₩246,193
₩274,998 total
includes taxes & fees
Sep 9 - Sep 10
11. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites16.9 km from Chesterwood
Jermaine
₩158,945
₩177,542 total
includes taxes & fees
Sep 1 - Sep 2
12. Little Cat Lodge
Little Cat Lodge16.3 km from Chesterwood
Kees
₩260,674
₩291,955 total
includes taxes & fees
Aug 23 - Aug 24
13. Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield15.5 km from Chesterwood
James
₩202,719
₩226,437 total
includes taxes & fees
Sep 13 - Sep 14
14. The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
Edward
₩273,862
₩314,120 total
includes taxes & fees
Aug 24 - Aug 25
15. Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge4.7 km from Chesterwood
Peter
₩96,038
₩105,353 total
includes taxes & fees
Aug 24 - Aug 25
16. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox14.9 km from Chesterwood
Sheila
₩109,481
₩122,290 total
includes taxes & fees
Sep 21 - Sep 22
17. The Central Downtown Inn & Suites
The Central Downtown Inn & Suites19.6 km from Chesterwood
Rena
₩127,095
₩141,960 total
includes taxes & fees
Sep 3 - Sep 4
18. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG15.5 km from Chesterwood
Ken
₩176,000
₩196,592 total
includes taxes & fees
Sep 21 - Sep 22
19. Berkshire Inn
Berkshire Inn19.1 km from Chesterwood
Adriana
₩124,711
₩139,303 total
includes taxes & fees
Aug 24 - Aug 25
20. The Whitlock
The Whitlock9.8 km from Chesterwood
Constance
₩235,671
₩263,244 total
includes taxes & fees
Sep 8 - Sep 9
Compare popular hotels close to Chesterwood
Property | Property class | 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 116 reviews | View | |||||
 Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires | 9.4 Exceptional 803 reviews | View | |||||
 Chambery Inn | 9.6 Exceptional 386 reviews | View | |||||
 The Yankee Inn | 9.2 Wonderful 1,017 reviews | View | |||||
 Berkshires Untold | 9.0 Wonderful 1,012 reviews | View |
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.