Find hotels near Chesterwood, South Lee from AED 351
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28 Aug - 30 Aug Our top choices for Chesterwood hotels
1. Berkshire Lake Lodge
Berkshire Lake Lodge16.2 km from Chesterwood
mike
AED 535
AED 598 total
includes taxes & fees
31 Aug - 1 Sep
2. Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
Richard
AED 1,429
AED 1,596 total
includes taxes & fees
3 Sep - 4 Sep
3. Chambery Inn
Chambery Inn8.7 km from Chesterwood
Richard
AED 992
AED 1,108 total
includes taxes & fees
19 Aug - 20 Aug
4. The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
Michele
AED 1,385
AED 1,624 total
includes taxes & fees
13 Sep - 14 Sep
5. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires12.5 km from Chesterwood
Lawrence
AED 683
AED 763 total
includes taxes & fees
17 Sep - 18 Sep
6. Wilder House Berkshires
Wilder House Berkshires19.9 km from Chesterwood
Jennifer
AED 736
AED 823 total
includes taxes & fees
27 Aug - 28 Aug
7. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce Resort6.7 km from Chesterwood
Claudia
AED 430
AED 552 total
includes taxes & fees
8 Sep - 9 Sep
8. East Rock Inn
East Rock Inn10.1 km from Chesterwood
ERIK
AED 463
AED 517 total
includes taxes & fees
17 Sep - 18 Sep
9. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG15.5 km from Chesterwood
Ken
AED 466
AED 521 total
includes taxes & fees
14 Sep - 15 Sep
10. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel8.6 km from Chesterwood
James
AED 468
AED 523 total
includes taxes & fees
14 Sep - 15 Sep
11. Brook Farm Inn
Brook Farm Inn9.1 km from Chesterwood
Carrie
AED 1,017
AED 1,165 total
includes taxes & fees
30 Aug - 31 Aug
12. Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield15.5 km from Chesterwood
James
AED 549
AED 614 total
includes taxes & fees
13 Sep - 14 Sep
13. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox14.7 km from Chesterwood
Nancy
AED 479
AED 535 total
includes taxes & fees
16 Sep - 17 Sep
14. The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
Karen
AED 580
AED 648 total
includes taxes & fees
14 Sep - 15 Sep
15. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires8.6 km from Chesterwood
Lisa
AED 715
AED 799 total
includes taxes & fees
23 Aug - 24 Aug
16. Berkshire Mountain Lodge
Berkshire Mountain Lodge15.9 km from Chesterwood
Robert
AED 347
AED 470 total
includes taxes & fees
31 Aug - 1 Sep
17. Hampton Terrace Inn
Hampton Terrace Inn9.8 km from Chesterwood
Kathleen
AED 804
AED 898 total
includes taxes & fees
10 Sep - 11 Sep
18. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
Christine
AED 393
AED 439 total
includes taxes & fees
31 Aug - 1 Sep
19. Berkshires Untold
Berkshires Untold13 km from Chesterwood
Pamela
AED 469
AED 524 total
includes taxes & fees
9 Sep - 10 Sep
20. Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
John
AED 314
AED 351 total
includes taxes & fees
1 Sep - 2 Sep
Top Chesterwood Hotel Reviews
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!"
Experienced Hosts. Quiet, Romantic, Spacious Apartment, Pet Friendly.
8/10 Good
"ok"
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"
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."
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"
Experienced Hosts, 10 min to Tanglewood, Quaint Berkshires Getaway
10/10 Excellent
"We had a very comfortable and relaxed stay. 3 real bedrooms and 2 bathrooms! Emily was a super responsive host whenever I had a question. Great location that allowed us to do everything we wanted to do very easily."
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.