Top Hotels Near Chesterwood in South Lee from AU$137
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18 Sept - 20 Sept 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
AU$186
includes taxes & fees
14 Sept - 15 Sept
2. Berkshire Lake Lodge
Berkshire Lake Lodge16.2 km from Chesterwood
mike
AU$213
includes taxes & fees
7 Sept - 8 Sept
3. The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
Karen
AU$180
includes taxes & fees
22 Sept - 23 Sept
4. Berkshire Mountain Lodge
Berkshire Mountain Lodge15.9 km from Chesterwood
Robert
AU$154
includes taxes & fees
1 Oct - 2 Oct
5. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox14.7 km from Chesterwood
Nancy
AU$198
includes taxes & fees
28 Sept - 29 Sept
6. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites16.9 km from Chesterwood
Prasanna
AU$139
includes taxes & fees
9 Sept - 10 Sept
7. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG15.5 km from Chesterwood
Steve
AU$197
includes taxes & fees
10 Sept - 11 Sept
8. The Little Lion
The Little Lion5.1 km from Chesterwood
Anne
AU$174
includes taxes & fees
7 Sept - 8 Sept
9. Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
Mervin
AU$220
includes taxes & fees
8 Sept - 9 Sept
10. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires12.5 km from Chesterwood
Lawrence
AU$302
includes taxes & fees
13 Sept - 14 Sept
11. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
Christine
AU$157
includes taxes & fees
27 Sept - 28 Sept
12. Sunset Inn
Sunset Inn9.1 km from Chesterwood
Joann
AU$137
includes taxes & fees
28 Sept - 29 Sept
13. The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
Jodi
AU$614
includes taxes & fees
13 Sept - 14 Sept
14. Little Cat Lodge
Little Cat Lodge16.3 km from Chesterwood
Kees
AU$278
includes taxes & fees
7 Sept - 8 Sept
15. Brook Farm Inn
Brook Farm Inn9.1 km from Chesterwood
Carrie
AU$401
includes taxes & fees
17 Sept - 18 Sept
16. Chambery Inn
Chambery Inn8.7 km from Chesterwood
Alexandra
AU$419
includes taxes & fees
7 Sept - 8 Sept
17. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG8 km from Chesterwood
BJORN
AU$205
includes taxes & fees
15 Sept - 16 Sept
18. The Central Downtown Inn & Suites
The Central Downtown Inn & Suites19.6 km from Chesterwood
Rena
AU$154
includes taxes & fees
7 Sept - 8 Sept
19. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires12.1 km from Chesterwood
Tracy
AU$276
includes taxes & fees
9 Sept - 10 Sept
20. Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield15.5 km from Chesterwood
James
AU$227
includes taxes & fees
10 Sept - 11 Sept
Top Chesterwood Hotel Reviews
The Red Lion Inn
10/10 Excellent
"Charming, updated throughout. Extremely clean and well appointed. Extremely delightful stay."
Hearth House | Prime Location!
10/10 Excellent
"Comfortable home in a great neighborhood."
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10/10 Excellent
"Our favorite place to rent in the Berkshires, with a perfect location, in Stockbridge. The owner responds to any message almost instantly. And she provides a cabinet of free candy! We will return next summer for our fourth year."
Stockbridge Village in Summer
10/10 Excellent
"I had a delightful 3 weeks at Claudia’s little farmhouse. The location was perfect in all respects…walk to coffee and patisserie shops, minutes by car to Tanglewood, The Mount, Norman Rockwell’s museum, etc etc etc. (The sitting room baby grand and the back yard laden pear tree were the cherries on top!) I look forward to another stay!"
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
10/10 Excellent
"Beautiful house, clean and sanitary. Enjoyed our stay immensely. Kudos to the house for putting together a fantastic environment."
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."
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
10/10 Excellent
"We love the beautiful Taggart River House! This was our second stay--eight of us really enjoyed our return visit to Stockbridge, Tanglewood and the Berkshires. The location is superb--walking distance to downtown Stockbridge can never be overrated. Short drives to everything else make this property ideal. Super responsive and helpful hosts! Very clean, well-appointed rooms and facilities, more than ample parking and easy-to-follow house rules and recommendations. Pictures are accurate. You will love it!"
Tranquil 3 BR Stockbridge House w/ Private Deck!
10/10 Excellent
"The house is lovely with a quirky charm. It is indeed a tranquil property surrounded by woods. Our hosts have thoughtfully overstocked the premises with towels, sheets, paper goods, and all sorts of kitchen tools and condiments. We had a lovely time."
Experienced Hosts. Quiet, Romantic, Spacious Apartment, Pet Friendly.
8/10 Good
"ok"
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.