Top Hotels Near Chesterwood in South Lee from NZ$162
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21 Aug - 23 Aug 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
NZ$678
includes taxes & fees
24 Aug - 25 Aug
2. The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
Merideth
NZ$382
includes taxes & fees
9 Sept - 10 Sept
3. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce Resort6.7 km from Chesterwood
Kimberly
NZ$236
includes taxes & fees
8 Sept - 9 Sept
4. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires8.6 km from Chesterwood
Lisa
NZ$369
includes taxes & fees
17 Aug - 18 Aug
5. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel8.6 km from Chesterwood
James
NZ$255
includes taxes & fees
7 Sept - 8 Sept
6. Berkshire Lake Lodge
Berkshire Lake Lodge16.2 km from Chesterwood
Rita
NZ$294
includes taxes & fees
8 Sept - 9 Sept
7. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
Jeanne
NZ$192
includes taxes & fees
31 Aug - 1 Sept
8. The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
Larry
NZ$313
includes taxes & fees
7 Sept - 8 Sept
9. East Rock Inn
East Rock Inn10.1 km from Chesterwood
ERIK
NZ$280
includes taxes & fees
23 Aug - 24 Aug
10. Berkshires Untold
Berkshires Untold13 km from Chesterwood
Ivana
NZ$246
includes taxes & fees
9 Sept - 10 Sept
11. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG8 km from Chesterwood
Kathleen
NZ$233
includes taxes & fees
9 Sept - 10 Sept
12. Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
John
NZ$162
includes taxes & fees
1 Sept - 2 Sept
13. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox14.7 km from Chesterwood
Nancy
NZ$272
includes taxes & fees
23 Aug - 24 Aug
14. The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
Edward
NZ$333
includes taxes & fees
31 Aug - 1 Sept
15. Berkshire Mountain Lodge
Berkshire Mountain Lodge15.9 km from Chesterwood
Joseph
NZ$217
includes taxes & fees
31 Aug - 1 Sept
16. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires12.5 km from Chesterwood
Lawrence
NZ$402
includes taxes & fees
19 Aug - 20 Aug
17. Chambery Inn
Chambery Inn8.7 km from Chesterwood
Joseph
NZ$512
includes taxes & fees
12 Aug - 13 Aug
18. The Little Lion
The Little Lion5.1 km from Chesterwood
Linda
NZ$213
includes taxes & fees
1 Sept - 2 Sept
19. Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
Christopher
NZ$737
includes taxes & fees
3 Sept - 4 Sept
20. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites16.9 km from Chesterwood
Jermaine
NZ$216
includes taxes & fees
30 Aug - 31 Aug
Compare popular hotels close to Chesterwood
Property | Property class | 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 1,015 reviews | View | |||||
 Holiday Inn Club Vacations Oak 'n Spruce Resort | 9.2 Wonderful 951 reviews | View | |||||
 Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires | 9.4 Exceptional 799 reviews | View | |||||
 The Black Swan Lee - Lenox, an Ascend Collection Hotel | 9.0 Wonderful 1,006 reviews | View |
Top Chesterwood Hotel Reviews
The Red Lion Inn
10/10 Excellent
"Excellent historic inn. We stay here every summer after a a concert at Tanglewood. Love it here."
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."
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.