Hotels near Chesterwood
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9 Sept - 10 SeptTomorrow
10 Sept - 11 SeptThis weekend
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18 Sept - 20 Sept Our top choices for Chesterwood hotels
1. The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
James
RM643
RM921 total
includes taxes & fees
30 Sept - 1 Oct
2. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel8.6 km from Chesterwood
Susan
RM518
RM579 total
includes taxes & fees
29 Sept - 30 Sept
3. The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
Karen
RM471
RM526 total
includes taxes & fees
22 Sept - 23 Sept
4. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce Resort6.7 km from Chesterwood
Linda
RM475
RM610 total
includes taxes & fees
13 Sept - 14 Sept
5. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
Christine
RM411
RM459 total
includes taxes & fees
30 Sept - 1 Oct
6. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires8.6 km from Chesterwood
Bruce
RM756
RM845 total
includes taxes & fees
14 Sept - 15 Sept
7. Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
Analisia
RM347
RM388 total
includes taxes & fees
10 Sept - 11 Sept
8. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG8 km from Chesterwood
BJORN
RM536
RM599 total
includes taxes & fees
15 Sept - 16 Sept
9. Berkshire Lake Lodge
Berkshire Lake Lodge16.2 km from Chesterwood
mike
RM618
RM690 total
includes taxes & fees
10 Sept - 11 Sept
10. The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
Edward
RM668
RM766 total
includes taxes & fees
10 Sept - 11 Sept
11. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires12.5 km from Chesterwood
Lawrence
RM792
RM885 total
includes taxes & fees
15 Sept - 16 Sept
12. The Little Lion
The Little Lion5.1 km from Chesterwood
Anne
RM457
RM510 total
includes taxes & fees
10 Sept - 11 Sept
13. Berkshires Untold
Berkshires Untold13 km from Chesterwood
David
RM535
RM597 total
includes taxes & fees
10 Sept - 11 Sept
14. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox14.7 km from Chesterwood
Nancy
RM526
RM587 total
includes taxes & fees
30 Sept - 1 Oct
15. Quality Inn Great Barrington
Quality Inn Great Barrington10.3 km from Chesterwood
Sisile
RM421
RM470 total
includes taxes & fees
13 Sept - 14 Sept
16. Berkshire Mountain Lodge
Berkshire Mountain Lodge15.9 km from Chesterwood
Robert
RM323
RM452 total
includes taxes & fees
1 Oct - 2 Oct
17. Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
Mervin
RM605
RM664 total
includes taxes & fees
10 Sept - 11 Sept
18. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG15.5 km from Chesterwood
Steve
RM496
RM554 total
includes taxes & fees
15 Sept - 16 Sept
19. Chambery Inn
Chambery Inn8.7 km from Chesterwood
Alexandra
RM1,097
RM1,225 total
includes taxes & fees
10 Sept - 11 Sept
20. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires12.1 km from Chesterwood
Tracy
RM811
RM906 total
includes taxes & fees
1 Oct - 2 Oct
Compare popular hotels close to Chesterwood
Property | Property class | Guest rating | Breakfast included | Pool | Spa | Pet-friendly | WiFi included |
|---|---|---|---|---|---|---|---|
 The Red Lion Inn | 8.8 Excellent 1,015 reviews | View | |||||
 The Black Swan Lee - Lenox, an Ascend Collection Hotel | 9.0 Wonderful 1,001 reviews | View | |||||
 The Yankee Inn | 9.2 Wonderful 1,020 reviews | View | |||||
 Holiday Inn Club Vacations Oak 'n Spruce Resort | 9.2 Wonderful 985 reviews | View | |||||
 Quality Inn Lee - Lenox South | 8.4 Very good 1,021 reviews | View |
Top Chesterwood Hotel Reviews
Holiday Inn Club Vacations Oak 'n Spruce Resort
8/10 Good
"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."
Pleasant Valley Motel West Stockbridge
8/10 Good
"I stay here a lot. Cheap and easy. Hot water, decent beds, yes, room is dated but its cheap and people are very nice. If you're looking for the Ritz Carleton this ain't it. If you're planning a budget weekend this works just fine"
The Little Lion
10/10 Excellent
"Easy check in. The rooms were clean. Beds comfy."
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 browsing the exhibits at Norman Rockwell Museum during your trip to 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 studying the exhibits at Mission House in Stockbridge. Wander the lakeside in this quaint area.
Naumkeag Museum
9.4/10 (10 reviews)
You can spend time studying the exhibits at Naumkeag Museum 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 studying the exhibits at Schantz Galleries during your travels in 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 during your trip to 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 enjoy a show at Berkshire Theatre Festival during your trip to Stockbridge. Wander the lakeside in this quaint area.