Find hotels near Chesterwood, South Lee from ￥15,209
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Aug 12 - Aug 13Tomorrow
Aug 13 - Aug 14This weekend
Aug 14 - Aug 16Next weekend
Aug 21 - Aug 23 Our top choices for Chesterwood hotels
1. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood0.6 km from Chesterwood
Philippe
￥52,580
￥63,607 total
includes taxes & fees
Sep 2 - Sep 3
2. The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
Merideth
￥25,549
￥36,450 total
includes taxes & fees
Sep 9 - Sep 10
3. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires8.6 km from Chesterwood
Lisa
￥30,998
￥34,625 total
includes taxes & fees
Aug 19 - Aug 20
4. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce Resort6.7 km from Chesterwood
Marc
￥17,056
￥22,164 total
includes taxes & fees
Sep 8 - Sep 9
5. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
Christine
￥17,058
￥19,054 total
includes taxes & fees
Aug 31 - Sep 1
6. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG8 km from Chesterwood
Kathleen
￥19,588
￥21,879 total
includes taxes & fees
Sep 9 - Sep 10
7. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel8.6 km from Chesterwood
James
￥21,387
￥23,889 total
includes taxes & fees
Sep 7 - Sep 8
8. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites16.9 km from Chesterwood
Jermaine
￥18,151
￥20,274 total
includes taxes & fees
Sep 7 - Sep 8
9. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox14.7 km from Chesterwood
Nancy
￥23,375
￥26,109 total
includes taxes & fees
Sep 7 - Sep 8
10. The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
Larry
￥26,276
￥29,350 total
includes taxes & fees
Sep 7 - Sep 8
11. East Rock Inn
East Rock Inn10.1 km from Chesterwood
ERIK
￥20,069
￥22,417 total
includes taxes & fees
Sep 9 - Sep 10
12. Berkshire Lake Lodge
Berkshire Lake Lodge16.2 km from Chesterwood
Rita
￥24,461
￥27,323 total
includes taxes & fees
Sep 8 - Sep 9
13. Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
John
￥13,616
￥15,209 total
includes taxes & fees
Sep 1 - Sep 2
14. Berkshires Untold
Berkshires Untold13 km from Chesterwood
Ivana
￥20,782
￥23,214 total
includes taxes & fees
Sep 10 - Sep 11
15. The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
Edward
￥28,326
￥32,591 total
includes taxes & fees
Aug 25 - Aug 26
16. Berkshire Mountain Lodge
Berkshire Mountain Lodge15.9 km from Chesterwood
Andrea
￥15,067
￥20,388 total
includes taxes & fees
Aug 31 - Sep 1
17. Chambery Inn
Chambery Inn8.7 km from Chesterwood
Joseph
￥42,996
￥48,026 total
includes taxes & fees
Aug 13 - Aug 14
18. Quality Inn Great Barrington
Quality Inn Great Barrington10.3 km from Chesterwood
Lynn
￥14,755
￥16,482 total
includes taxes & fees
Sep 2 - Sep 3
19. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires12.5 km from Chesterwood
Lawrence
￥33,709
￥37,654 total
includes taxes & fees
Aug 23 - Aug 24
20. The Little Lion
The Little Lion5.1 km from Chesterwood
Linda
￥17,915
￥20,010 total
includes taxes & fees
Sep 8 - Sep 9
Compare popular hotels close to Chesterwood
Property | Star rating | Guest rating | Breakfast included | Pool | Spa | Pet friendly | WiFi included |
|---|---|---|---|---|---|---|---|
 The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood | 9.2 Wonderful 114 reviews | View | |||||
 The Red Lion Inn | 8.8 Excellent 1,017 reviews | View | |||||
 Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires | 9.4 Exceptional 799 reviews | View | |||||
 Holiday Inn Express Hotel & Suites Great Barrington by IHG | 8.8 Excellent 800 reviews | View | |||||
 Best Western Plus Berkshire Hills Inn & Suites | 8.6 Excellent 1,005 reviews | View |
Top Chesterwood Hotel Reviews
The Red Lion Inn
10/10 Excellent
"This is an old inn. It’s elegant, fun and very comfortable. Lots of dark, antique furniture and communal card games. The staff is friendly and some have been there many years. Many of the guests return year after year. If that’s what you’re looking for, you will love it. I do. If you are looking for sleek and spotless, you are best suited elsewhere."
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."
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.