Hotels near Chesterwood
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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, (112 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
Deborah
The price is RM1,344
RM1,626 total
includes taxes & fees
26 Jul - 27 Jul
The Red Lion Inn
The Red Lion Inn3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,012 reviews)
"Excellent stay. Such history and attention to detail. Some areas showing some wear but this is a great place to stay."
Allen
The price is RM697
RM961 total
includes taxes & fees
22 Jul - 23 Jul
The Little Lion
The Little Lion5.1 km from Chesterwood
8.6 out of 10, Excellent, (581 reviews)
"Such a peaceful and easy stay!"
Mia
The price is RM456
RM509 total
includes taxes & fees
13 Jul - 14 Jul
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, (789 reviews)
"very responsive staff excellent check in and check out"
Kathleen
The price is RM627
RM700 total
includes taxes & fees
26 Jul - 27 Jul
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, (931 reviews)
"Wonderful stay for families."
Kimberly
The price is RM638
RM793 total
includes taxes & fees
29 Jul - 30 Jul
Granville House
Granville House6.4 km from Chesterwood
10.0 out of 10, Exceptional, (102 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
Nicole
The price is RM1,120
RM1,251 total
includes taxes & fees
13 Jul - 14 Jul
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, (794 reviews)
"Extremely friendly and helpful staff upon arrival. Provide great insights on local restaurant opportunities, and included a five star breakfast. Highly recommend!"
Lisa
The price is RM793
RM885 total
includes taxes & fees
10 Aug - 11 Aug
Monument Mountain Motel
Monument Mountain Motel8.7 km from Chesterwood
9.0 out of 10, Wonderful, (878 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens)
Loved the place."
Yekaterina
The price is RM453
RM506 total
includes taxes & fees
13 Jul - 14 Jul
Shaker Mill Inn
Shaker Mill Inn5.8 km from Chesterwood
9.6 out of 10, Exceptional, (464 reviews)
"Wonderful place to stay!"
Mervin
The price is RM770
RM844 total
includes taxes & fees
13 Jul - 14 Jul
The Inn at Stockbridge
The Inn at Stockbridge5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
Stephen
The price is RM1,559
RM1,828 total
includes taxes & fees
20 Jul - 21 Jul
Devonfield Inn B&B
Devonfield Inn B&B7.5 km from Chesterwood
10.0 out of 10, Exceptional, (139 reviews)
"Room was great, staff was awesome, amenities were cool"
Francis
The price is RM1,788
RM1,997 total
includes taxes & fees
13 Jul - 14 Jul
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires6.2 km from Chesterwood
7.6 out of 10, Good, (592 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 RM403
RM450 total
includes taxes & fees
19 Jul - 20 Jul
Quality Inn Great Barrington
Quality Inn Great Barrington10.3 km from Chesterwood
8.6 out of 10, Excellent, (1,015 reviews)
"Great staff. Clean comfortable rooms. Good pillows and mattress and cold A/C"
sarah
The price is RM481
RM537 total
includes taxes & fees
10 Aug - 11 Aug
Chambery Inn
Chambery Inn8.7 km from Chesterwood
9.6 out of 10, Exceptional, (381 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
Joseph
The price is RM1,099
RM1,228 total
includes taxes & fees
13 Jul - 14 Jul
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge4.7 km from Chesterwood
6.8 out of 10, (1,003 reviews)
"The property is in terrible condition."
Olga V
The price is RM275
RM302 total
includes taxes & fees
13 Jul - 14 Jul
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,006 reviews)
"The staff were super friendly"
John
The price is RM882
RM1,014 total
includes taxes & fees
20 Jul - 21 Jul
The Whitlock
The Whitlock9.8 km from Chesterwood
8.4 out of 10, Very good, (323 reviews)
"A beautiful old inn in the heart of a lovely old town."
Linda
The price is RM631
RM705 total
includes taxes & fees
20 Jul - 21 Jul
East Rock Inn
East Rock Inn10.1 km from Chesterwood
9.4 out of 10, Exceptional, (49 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 RM743
RM830 total
includes taxes & fees
19 Jul - 20 Jul
The Yankee Inn
The Yankee Inn14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,013 reviews)
"Great location with easy parking
Excellent cleaning staff. Done promptly and right. Very helpful front desk staff."
Brian
The price is RM616
RM688 total
includes taxes & fees
13 Jul - 14 Jul
Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires12.5 km from Chesterwood
9.8 out of 10, Exceptional, (28 reviews)
"Friendly staff, beautiful interiors."
Izabela
The price is RM932
RM1,042 total
includes taxes & fees
27 Jul - 28 Jul
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 112 reviews | View | ||||||
 The Red Lion Inn | 8.8 Excellent 1,012 reviews | View | ||||||
 The Little Lion | 8.6 Excellent 581 reviews | View | ||||||
 Holiday Inn Express Hotel & Suites Great Barrington by IHG | 8.8 Excellent 789 reviews | View | ||||||
 Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG | 9.2 Wonderful 931 reviews | View |
Top Chesterwood Hotel Reviews
The Little Lion
10/10 Excellent
