Search Hotels Near Chesterwood, South Lee
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21 Aug - 23 Aug Our top choices for Chesterwood hotels
1. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel5.3 mi from Chesterwood
James
£111
includes taxes & fees
7 Sept - 8 Sept
2. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South5.7 mi from Chesterwood
Christine
£89
includes taxes & fees
31 Aug - 1 Sept
3. Berkshire Lake Lodge
Berkshire Lake Lodge10 mi from Chesterwood
Rita
£130
includes taxes & fees
31 Aug - 1 Sept
4. The Yankee Inn
The Yankee Inn9.3 mi from Chesterwood
Karen
£136
includes taxes & fees
7 Sept - 8 Sept
5. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires5.3 mi from Chesterwood
Lisa
£161
includes taxes & fees
17 Aug - 18 Aug
6. Monument Mountain Motel
Monument Mountain Motel5.4 mi from Chesterwood
John
£71
includes taxes & fees
1 Sept - 2 Sept
7. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce Resort4.2 mi from Chesterwood
Marc
£111
includes taxes & fees
10 Sept - 11 Sept
8. The Little Lion
The Little Lion3.2 mi from Chesterwood
Linda
£93
includes taxes & fees
1 Sept - 2 Sept
9. The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires6.7 mi from Chesterwood
Edward
£151
includes taxes & fees
25 Aug - 26 Aug
10. East Rock Inn
East Rock Inn6.3 mi from Chesterwood
ERIK
£104
includes taxes & fees
9 Sept - 10 Sept
11. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires7.8 mi from Chesterwood
Lawrence
£159
includes taxes & fees
19 Aug - 20 Aug
12. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox9.1 mi from Chesterwood
Nancy
£114
includes taxes & fees
13 Sept - 14 Sept
13. Chambery Inn
Chambery Inn5.4 mi from Chesterwood
Joseph
£223
includes taxes & fees
17 Aug - 18 Aug
14. Berkshire Mountain Lodge
Berkshire Mountain Lodge9.9 mi from Chesterwood
Karilyn
£95
includes taxes & fees
31 Aug - 1 Sept
15. Devonfield Inn B&B
Devonfield Inn B&B4.7 mi from Chesterwood
Richard
£322
includes taxes & fees
3 Sept - 4 Sept
16. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG9.6 mi from Chesterwood
Ken
£108
includes taxes & fees
7 Sept - 8 Sept
17. Shaker Mill Inn
Shaker Mill Inn3.6 mi from Chesterwood
Mervin
£158
includes taxes & fees
8 Sept - 9 Sept
18. Quality Inn Great Barrington
Quality Inn Great Barrington6.4 mi from Chesterwood
Lynn
£77
includes taxes & fees
2 Sept - 3 Sept
19. The Whitlock
The Whitlock6.1 mi from Chesterwood
James
£123
includes taxes & fees
13 Sept - 14 Sept
20. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites10.5 mi from Chesterwood
Jermaine
£94
includes taxes & fees
30 Aug - 31 Aug
Top Chesterwood Hotel Reviews
The Little Lion
10/10 Excellent
"Great location. Functional and affordable. Pet friendly."
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
10/10 Excellent
"Very lovely beautiful Room and property The outside pool was not available"
Stockbridge Village in Summer
10/10 Excellent
"Nice two bedroom home within easy walking distance to the Stockbridge Center. The owner Claudia was very helpful with information concerning the home. I would highly recommend this home for a couple or a small family."
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."
Secluded Family Home in Serene Stockbridge Woods
10/10 Excellent
"Tom was a great host. Easy to communicate and just a nice guy. The property was in a great location close to all the places we went to-Tanglewood, Norman Rockwell Museum, Botanical Gardens, Lenox, Stockbridge and more. Home was very spacious with a great outdoor deck. Nice grill that we used several times. Would definitely stay there again."
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."
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
8/10 Good
"This house is magnificent but unfortunately is not maintained well. The basement bedroom had not been cleaned and had spiders. The shower was so dirty that we did not use it. The picture of the deck has an umbrella for shade. No umbrella and the furniture cover was upside down on the deck full of stagnant water. The photos of the garden were deceiving as the raised beds were full of weeds and the lawn has not been mowed for a long time. There were strict instructions for taking out the trash but could not be followed as the trash had not been picked up from the previous tenant. We paid a lot of money to rent this house and don't feel that it lived up to its description."
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."
Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests
10/10 Excellent
"Large comfortable house, in a beautiful location with a large grassy back yard, and right next to a lovely church. Plus totally central to the village of Stockbridge and to trails going along the Housatonic River and up into a state forrest. Loved it"
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.