Find hotels near Chesterwood, South Lee from NT$3,023
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Sep 2 - Sep 3Tomorrow
Sep 3 - Sep 4This weekend
Sep 4 - Sep 6Next weekend
Sep 11 - Sep 13 Our top choices for Chesterwood hotels
1. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce Resort6.7 km from Chesterwood
Linda
NT$3,248
NT$4,247 total
includes taxes & fees
Sep 16 - Sep 17
2. The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
Karen
NT$2,935
NT$3,278 total
includes taxes & fees
Sep 9 - Sep 10
3. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel8.6 km from Chesterwood
James
NT$4,036
NT$4,508 total
includes taxes & fees
Sep 24 - Sep 25
4. The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
Patricia
NT$5,181
NT$7,360 total
includes taxes & fees
Sep 30 - Oct 1
5. Berkshire Lake Lodge
Berkshire Lake Lodge16.2 km from Chesterwood
mike
NT$4,629
NT$5,171 total
includes taxes & fees
Sep 8 - Sep 9
6. Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
Charlie
NT$2,706
NT$3,023 total
includes taxes & fees
Sep 7 - Sep 8
7. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires8.6 km from Chesterwood
Lisa
NT$5,085
NT$5,680 total
includes taxes & fees
Sep 7 - Sep 8
8. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
Christine
NT$3,471
NT$3,877 total
includes taxes & fees
Sep 22 - Sep 23
9. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG8 km from Chesterwood
BJORN
NT$3,516
NT$3,928 total
includes taxes & fees
Sep 7 - Sep 8
10. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox14.7 km from Chesterwood
Nancy
NT$4,086
NT$4,564 total
includes taxes & fees
Sep 30 - Oct 1
11. The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
FRED
NT$6,430
NT$7,375 total
includes taxes & fees
Sep 8 - Sep 9
12. Berkshires Untold
Berkshires Untold13 km from Chesterwood
David
NT$4,429
NT$4,947 total
includes taxes & fees
Sep 28 - Sep 29
13. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires12.5 km from Chesterwood
Lawrence
NT$5,639
NT$6,298 total
includes taxes & fees
Sep 9 - Sep 10
14. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites16.9 km from Chesterwood
Prasanna
NT$2,846
NT$3,179 total
includes taxes & fees
Sep 8 - Sep 9
15. Berkshire Mountain Lodge
Berkshire Mountain Lodge15.9 km from Chesterwood
Robert
NT$2,520
NT$3,521 total
includes taxes & fees
Oct 1 - Oct 2
16. The Little Lion
The Little Lion5.1 km from Chesterwood
Anne
NT$3,561
NT$3,978 total
includes taxes & fees
Sep 8 - Sep 9
17. East Rock Inn
East Rock Inn10.1 km from Chesterwood
ERIK
NT$4,377
NT$4,889 total
includes taxes & fees
Sep 22 - Sep 23
18. Quality Inn Great Barrington
Quality Inn Great Barrington10.3 km from Chesterwood
Sisile
NT$2,933
NT$3,276 total
includes taxes & fees
Sep 24 - Sep 25
19. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG15.5 km from Chesterwood
Steve
NT$3,735
NT$4,172 total
includes taxes & fees
Sep 8 - Sep 9
20. Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
Richard
NT$12,322
NT$13,764 total
includes taxes & fees
Sep 3 - Sep 4
Top Chesterwood Hotel Reviews
Pleasant Valley Motel West Stockbridge
8/10 Good
"Perfect price, good location if you like to sleep with the windows open and don't mind a little highway noise. Convenient to the highway, obviously, as well as both Lee and Stockbridge Centers (we enjoyed stopping at local thrifting stores) Tanglewood (we had free tickets) and several great eateries. Bed was comfortable enough, hot water, clean sheets and towels ... but that smell. A bit musty!"
The Inn at Stockbridge
10/10 Excellent
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
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."
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.
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- Animagic Museum of Animation
- Greenock Country Club
- Visit South Lee
- Norman Rockwell Museum
- Bousquet Ski Area
- Frelinghuysen Morris House and Studio
- Pleasant Valley Wilderness Sanctuary
- Visit Housatonic
- Visit South Egremont
- Visit Lee
- Visit Lenox
- National Shrine of the Divine Mercy
- Lenox Mountain
- Lee Premium Outlets
- Berkshire Botanical Garden
- Visit West Stockbridge
- Visit Great Barrington
- Mission House
- South Lee Vacations
- Charles H. Baldwin & Sons