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Tonight
Aug 13 - Aug 14Tomorrow
Aug 14 - Aug 15This weekend
Aug 14 - Aug 16Next weekend
Aug 21 - Aug 23 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
$134 nightly
$150 total
Sep 7 - Sep 8
Total with taxes and fees




2. Berkshire Lake Lodge
Berkshire Lake Lodge10 mi from Chesterwood
Rita
$154 nightly
$172 total
Aug 31 - Sep 1
Total with taxes and fees




3. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South5.7 mi from Chesterwood
Christine
$107 nightly
$120 total
Aug 31 - Sep 1
Total with taxes and fees




4. The Yankee Inn
The Yankee Inn9.3 mi from Chesterwood
Karen
$165 nightly
$184 total
Sep 7 - Sep 8
Total with taxes and fees




5. The Red Lion Inn
The Red Lion Inn2.1 mi from Chesterwood
Merideth
$215 nightly
$240 total
Sep 9 - Sep 10
Total with taxes and fees




6. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires5.3 mi from Chesterwood
Lisa
$195 nightly
$217 total
Aug 19 - Aug 20
Total with taxes and fees




7. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG5 mi from Chesterwood
Kathleen
$119 nightly
$133 total
Sep 13 - Sep 14
Total with taxes and fees




8. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce Resort4.2 mi from Chesterwood
Marc
$135 nightly
$150 total
Sep 10 - Sep 11
Total with taxes and fees




9. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox9.1 mi from Chesterwood
Nancy
$130 nightly
$146 total
Sep 13 - Sep 14
Total with taxes and fees




10. Shaker Mill Inn
Shaker Mill Inn3.6 mi from Chesterwood
Mervin
$176 nightly
$193 total
Sep 8 - Sep 9
Total with taxes and fees




11. Monument Mountain Motel
Monument Mountain Motel5.4 mi from Chesterwood
John
$95 nightly
$106 total
Sep 1 - Sep 2
Total with taxes and fees




12. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires7.8 mi from Chesterwood
Lawrence
$203 nightly
$227 total
Sep 7 - Sep 8
Total with taxes and fees




13. Berkshire Mountain Lodge
Berkshire Mountain Lodge9.9 mi from Chesterwood
Karilyn
$125 nightly
$139 total
Aug 31 - Sep 1
Total with taxes and fees




14. Quality Inn Great Barrington
Quality Inn Great Barrington6.4 mi from Chesterwood
Lynn
$93 nightly
$103 total
Sep 7 - Sep 8
Total with taxes and fees




15. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites10.5 mi from Chesterwood
Jermaine
$114 nightly
$127 total
Aug 30 - Aug 31
Total with taxes and fees




16. Devonfield Inn B&B
Devonfield Inn B&B4.7 mi from Chesterwood
Richard
$389 nightly
$435 total
Sep 3 - Sep 4
Total with taxes and fees




17. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG9.6 mi from Chesterwood
Ken
$131 nightly
$146 total
Sep 7 - Sep 8
Total with taxes and fees




18. The Little Lion
The Little Lion3.2 mi from Chesterwood
Linda
$125 nightly
$140 total
Sep 1 - Sep 2
Total with taxes and fees




19. Chambery Inn
Chambery Inn5.4 mi from Chesterwood
Joseph
$300 nightly
$335 total
Aug 16 - Aug 17
Total with taxes and fees




20. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires7.5 mi from Chesterwood
Laura
$186 nightly
$208 total
Aug 19 - Aug 20
Total with taxes and fees
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 Cottage With Mountain View’s and walk to town
10/10 Excellent
"The cottage was comfortable for a rainy, two night stay for 5 adults and our dog. The fenced in yard was perfect for the dog! We had enough dry weather to hike up to the fire tower via a trail walking distance from the cottage. We enjoyed cooking in the well equipped kitchen and using the grill on the deck. We also enjoyed a meal at The Red Lion Inn, right down the street.Thanks for accommodating us!"
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."
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.
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- Naumkeag Museum
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- Visit South Lee
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- Visit Great Barrington
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- Mission House
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