South Lee Chesterwood Hotels
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28 Aug - 30 AugNext weekend
4 Sept - 6 Sept Our top choices for Chesterwood hotels
1. The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
Patricia
HK$1,234
HK$1,768 total
includes taxes & fees
8 Sept - 9 Sept
2. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce Resort6.7 km from Chesterwood
Claudia
HK$917
HK$1,177 total
includes taxes & fees
31 Aug - 1 Sept
3. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel8.6 km from Chesterwood
Rinat
HK$999
HK$1,116 total
includes taxes & fees
21 Sept - 22 Sept
4. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG8 km from Chesterwood
BJORN
HK$964
HK$1,077 total
includes taxes & fees
23 Sept - 24 Sept
5. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires8.6 km from Chesterwood
Lisa
HK$1,525
HK$1,704 total
includes taxes & fees
8 Sept - 9 Sept
6. East Rock Inn
East Rock Inn10.1 km from Chesterwood
ERIK
HK$988
HK$1,104 total
includes taxes & fees
14 Sept - 15 Sept
7. The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
Karen
HK$1,238
HK$1,383 total
includes taxes & fees
14 Sept - 15 Sept
8. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox14.7 km from Chesterwood
Nancy
HK$1,021
HK$1,141 total
includes taxes & fees
24 Sept - 25 Sept
9. Berkshire Lake Lodge
Berkshire Lake Lodge16.2 km from Chesterwood
mike
HK$1,166
HK$1,302 total
includes taxes & fees
31 Aug - 1 Sept
10. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
Christine
HK$859
HK$960 total
includes taxes & fees
15 Sept - 16 Sept
11. Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
John
HK$670
HK$748 total
includes taxes & fees
1 Sept - 2 Sept
12. Berkshires Untold
Berkshires Untold13 km from Chesterwood
Christine
HK$1,111
HK$1,241 total
includes taxes & fees
8 Sept - 9 Sept
13. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires12.5 km from Chesterwood
Lawrence
HK$1,528
HK$1,707 total
includes taxes & fees
31 Aug - 1 Sept
14. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG15.5 km from Chesterwood
Ken
HK$933
HK$1,042 total
includes taxes & fees
24 Sept - 25 Sept
15. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires12.1 km from Chesterwood
Laura
HK$1,392
HK$1,555 total
includes taxes & fees
8 Sept - 9 Sept
16. The Little Lion
The Little Lion5.1 km from Chesterwood
Anne
HK$882
HK$985 total
includes taxes & fees
1 Sept - 2 Sept
17. The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
Edward
HK$1,549
HK$1,776 total
includes taxes & fees
31 Aug - 1 Sept
18. Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
Mervin
HK$1,403
HK$1,539 total
includes taxes & fees
26 Aug - 27 Aug
19. Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
Richard
HK$3,048
HK$3,405 total
includes taxes & fees
3 Sept - 4 Sept
20. Quality Inn Great Barrington
Quality Inn Great Barrington10.3 km from Chesterwood
Sisile
HK$726
HK$811 total
includes taxes & fees
15 Sept - 16 Sept
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 1,014 reviews | View | |||||
 Holiday Inn Club Vacations Oak 'n Spruce Resort | 9.2 Wonderful 970 reviews | View | |||||
 The Black Swan Lee - Lenox, an Ascend Collection Hotel | 9.0 Wonderful 1,010 reviews | View | |||||
 Holiday Inn Express Hotel & Suites Great Barrington by IHG | 8.8 Excellent 808 reviews | View | |||||
 Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires | 9.4 Exceptional 805 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."
Stockbridge Village Cottage With Mountain View’s and walk to town
10/10 Excellent
"We have stayed here several times. It is a perfect spot for enjoying the Berkshires!! It is close to Tanglewood, all of the theaters and wonderful places to eat. The hosts are wonderful. We feel like this is our home in the Berkshires"
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!"
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"
Hearth House | Prime Location!
10/10 Excellent
"This property was better than expected! The photos don’t do it justice. It was ideal for my husband and me to share with our son and small granddaughter with them having their privacy upstairs, but ample room for us to all be together downstairs, and a wonderful bedroom suite for us. The yard and patio are lovely. We so appreciated the ample supplies provided (at some rentals we’ve had to run to a store to augment things that ran out) and the well appointed kitchen. We love the area and we’re only sorry our stay wasn’t long enough to take full advantage of everything on and off site. My only suggestion is that the information provided upon leaving would be helpful to have upfront, particularly because some things mentioned differed from information in the handbook on the property, and it would help to plan better for day of departure. Oh, and communication was terrific with Jayren being very responsive to any questions."
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
10/10 Excellent
"The property was beautiful and perfectly located for our trip to hike the AT in Massachusetts."
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
10/10 Excellent
"Our family group had a great time at this property. We loved playing in barbecuing in the yard and the kids absolutely loved the basement with all of the toys and space for activities. The house had everything we needed!It is good to know that cell phone service is tricky in the area so if you need directions or to communicate with someone, make sure you do it when you’re on Wi-Fi before you pull out the driveway."
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.