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Our top choices for Chesterwood hotels
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
9.2 out of 10, Wonderful, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
Deborah
The price is 8.146.488 ₫
9.855.126 ₫ total
includes taxes & fees
25 May - 26 May
The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,010 reviews)
"a delightful inn centrally located in charming Stockbridge"
molly
The price is 4.119.989 ₫
5.777.513 ₫ total
includes taxes & fees
19 May - 20 May
Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (453 reviews)
"Everything was excellent"
Barbara
The price is 2.869.316 ₫
3.147.640 ₫ total
includes taxes & fees
13 May - 14 May
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG6.6 km from Chesterwood
9.2 out of 10, Wonderful, (892 reviews)
"Great place for a family vacation. Lots of activities for kids and peaceful location in the Berkshires. "
Khary
The price is 3.364.207 ₫
4.272.454 ₫ total
includes taxes & fees
18 May - 19 May
The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (559 reviews)
"A nice safe and quiet place to stay. Park right in front of your door. My dog loved the large grass area. The room was large and the beds very comfortable. The heat was on when we arrived which was great . It was cold and snowy that day. I loved having the self check-in and check out. We plan on going back the next time we are in the area.
"
SUSAN
The price is 2.500.780 ₫
2.793.370 ₫ total
includes taxes & fees
11 Jun - 12 Jun
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel8.6 km from Chesterwood
9.2 out of 10, Wonderful, (1,010 reviews)
"Nice location. Can rent their pontoon boat."
Paul
The price is 3.196.787 ₫
3.570.811 ₫ total
includes taxes & fees
27 May - 28 May
Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (851 reviews)
"Very clean and cozy in a great location! "
Lidia
The price is 1.800.562 ₫
2.011.154 ₫ total
includes taxes & fees
19 May - 20 May
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG8 km from Chesterwood
8.8 out of 10, Excellent, (764 reviews)
"Nice clean room, clean and well maintained breakfast was tasteful each day. Desk Clerk very helpful in giving out direction, Breaksfast person, very friendly. Hotel is centrally located, shop and restaurant nearby"
Berdest
The price is 3.264.176 ₫
3.646.137 ₫ total
includes taxes & fees
27 May - 28 May
The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
Steven
The price is 6.917.947 ₫
8.113.846 ₫ total
includes taxes & fees
25 May - 26 May
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires8.6 km from Chesterwood
9.4 out of 10, Exceptional, (780 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
Helena
The price is 4.676.459 ₫
5.223.605 ₫ total
includes taxes & fees
17 May - 18 May
Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
Christopher
The price is 7.081.156 ₫
7.909.572 ₫ total
includes taxes & fees
13 May - 14 May
Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
robert
The price is 4.498.602 ₫
5.024.939 ₫ total
includes taxes & fees
13 May - 14 May
Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South9.1 km from Chesterwood
8.4 out of 10, Very good, (1,004 reviews)
"Great location "
Edith
The price is 2.988.300 ₫
3.337.931 ₫ total
includes taxes & fees
9 Jun - 10 Jun
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (578 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
Heather
The price is 1.973.175 ₫
2.204.037 ₫ total
includes taxes & fees
18 May - 19 May
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge4.7 km from Chesterwood
6.8 out of 10, (1,003 reviews)
"Rooms need an update badly."
john
The price is 1.657.467 ₫
1.818.242 ₫ total
includes taxes & fees
27 May - 28 May
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,003 reviews)
"enjoy your vacation"
lev
The price is 3.508.463 ₫
4.036.522 ₫ total
includes taxes & fees
13 May - 14 May
The Whitlock
The Whitlock9.8 km from Chesterwood
8.6 out of 10, Excellent, (299 reviews)
"Lovely historical hotel within walking distance to many great shops and restaurants. Staff members maintained good communication and were very helpful throughout our stay. Rooms were clean, quiet, and comfortable. Would definitely stay there again."
Elaine
The price is 3.065.167 ₫
3.423.791 ₫ total
includes taxes & fees
26 May - 27 May
East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.4 out of 10, Exceptional, (44 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
Laura
The price is 3.911.622 ₫
4.369.282 ₫ total
includes taxes & fees
17 May - 18 May
Element Lenox Berkshires
Element Lenox Berkshires12.5 km from Chesterwood
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
Izabela
The price is 4.393.603 ₫
4.907.654 ₫ total
includes taxes & fees
20 May - 21 May
Berkshires Untold
Berkshires Untold13 km from Chesterwood
9.0 out of 10, Wonderful, (938 reviews)
"Great stay!"
Aditya
The price is 2.822.430 ₫
3.152.653 ₫ total
includes taxes & fees
20 May - 21 May
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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 111 reviews | View | ||||||
 The Red Lion Inn | 8.8 Excellent 1,010 reviews | View | ||||||
 Shaker Mill Inn | 9.6 Exceptional 453 reviews | View | ||||||
 Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG | 9.2 Wonderful 892 reviews | View | ||||||
 The Little Lion | 8.6 Excellent 559 reviews | View |
Top Chesterwood Hotel Reviews
The Red Lion Inn
10/10 Excellent
