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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 Chesterwood
4.5 star property
0.6 km from Chesterwood
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is ₩466,600
₩564,464 total
includes taxes & fees
Apr 10 - Apr 11
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,000 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is ₩202,645
₩293,873 total
includes taxes & fees
Apr 7 - Apr 8
The Red Lion Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is ₩164,344
₩180,284 total
includes taxes & fees
Apr 1 - Apr 2
Shaker Mill Inn

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (555 reviews)
"Clean … check in , good location for us .. we’ll be back in Maynn"
United States
Kathleen
The price is ₩165,851
₩185,256 total
includes taxes & fees
Apr 8 - Apr 9
The Little Lion

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is ₩342,729
₩401,981 total
includes taxes & fees
Apr 3 - Apr 4
The Inn at Stockbridge

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8 km from Chesterwood
8.8 out of 10, Excellent, (752 reviews)
"This is not my first stay. Great hotel to stay for ski trips "
United States
Michael
The price is ₩187,383
₩209,307 total
includes taxes & fees
Apr 3 - Apr 4
Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
8.6 km from Chesterwood
9.2 out of 10, Wonderful, (1,001 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is ₩153,608
₩171,576 total
includes taxes & fees
Apr 6 - Apr 7
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Chambery Inn

Chambery Inn
3.0 star property
8.7 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. "
United States
robert
The price is ₩258,392
₩288,630 total
includes taxes & fees
Apr 27 - Apr 28
Chambery Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is ₩496,046
₩554,079 total
includes taxes & fees
Mar 30 - Mar 31
Devonfield Inn B&B

Brook Farm Inn

Brook Farm Inn
3.5 star property
9.1 km from Chesterwood
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
The price is ₩262,018
₩300,220 total
includes taxes & fees
Apr 24 - Apr 25
Brook Farm Inn

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
4.7 km from Chesterwood
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is ₩88,203
₩96,759 total
includes taxes & fees
Mar 29 - Mar 30
Pleasant Valley Motel West Stockbridge

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
6.2 km from Chesterwood
7.6 out of 10, Good, (574 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is ₩113,081
₩126,319 total
includes taxes & fees
Apr 1 - Apr 2
Travelodge by Wyndham Great Barrington Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
8.6 km from Chesterwood
9.4 out of 10, Exceptional, (776 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is ₩229,695
₩256,570 total
includes taxes & fees
Apr 5 - Apr 6
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
10.3 km from Chesterwood
8.4 out of 10, Very Good, (1,002 reviews)
"Great location, friendly staff"
United States
James
The price is ₩101,474
₩113,346 total
includes taxes & fees
Apr 16 - Apr 17
Quality Inn Great Barrington

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.6 out of 10, Exceptional, (24 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is ₩210,050
₩234,626 total
includes taxes & fees
Apr 8 - Apr 9
Element Lenox Berkshires

Berkshires Untold

Berkshires Untold
3.5 star property
13 km from Chesterwood
9.0 out of 10, Wonderful, (881 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is ₩105,538
₩117,886 total
includes taxes & fees
Apr 1 - Apr 2
Berkshires Untold

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.4 out of 10, Exceptional, (41 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is ₩204,033
₩227,904 total
includes taxes & fees
Apr 15 - Apr 16
East Rock Inn

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
12.1 km from Chesterwood
9.2 out of 10, Wonderful, (610 reviews)
"Clean room, friendly and helpful staff. "
United States
Jennifer
The price is ₩222,139
₩248,130 total
includes taxes & fees
Apr 23 - Apr 24
Courtyard by Marriott Lenox Berkshires

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (292 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."
United States
Elaine
The price is ₩197,961
₩221,123 total
includes taxes & fees
Apr 3 - Apr 4
The Whitlock

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
10.7 km from Chesterwood
9.0 out of 10, Wonderful, (1,000 reviews)
"Beautiful Inn, hosts are most welcome and the breakfast was perfect. Heading back for certain!"
United States
Karen
The price is ₩207,700
₩238,961 total
includes taxes & fees
Mar 30 - Mar 31
The Cornell Inn, Lenox & The Berkshires
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
Suite, Private Bathroom (RedBird Suite) | View from room
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2
Wonderful
110 reviews
View
Exterior
The Red Lion Inn
3.5 star property
8.8
Excellent
1,000 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
446 reviews
View
Exterior
The Little Lion
3.0 star property
8.6
Excellent
555 reviews
View
Front of property
The Inn at Stockbridge
4.0 star property
9.8
Exceptional
99 reviews
View

Top Chesterwood Hotel Reviews

Hotels near other Chesterwood attractions

Frequently asked questions

What's the area like around Chesterwood?
Chesterwood is located in a scenic area of South Lee known for its beautiful lakeside setting and hiking. If you're looking for a convenient place to stay, check out the 10 hotels and other accommodations you'll find within a mile.
What's the best hotel to stay close to Chesterwood?
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is one of the top choices for your stay based on our traveler data, and this B&B offers free breakfast and free parking. It's located just a short 0.4 mi (0.6 km) from Chesterwood. Another good choice is The Red Lion Inn, located 2.1 mi (3.3 km) away.
How many hotels are there close to Chesterwood?
Expedia has 10 hotels and other accommodations within a mile from Chesterwood.
If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?
Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to review the best options available near Chesterwood.
Where can I learn more about changing or cancelling my trip in the area near Chesterwood?
For more information about picking new dates or cancelling your stay near Chesterwood, head over to our customer service page.
What can I see and do near Chesterwood?
You'll want to browse the exhibits at Norman Rockwell Museum and Mission House. Naumkeag Museum, The Mount, and Berkshire Theatre Festival are monuments to see when you're exploring the area around Chesterwood. Be sure to get some family photos at Berkshire Botanical Garden, Hoffman's Pottery, and Lenox Arts Center while you're out sightseeing near Chesterwood.