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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, (111 reviews)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is ฿9,963
฿12,053 total
includes taxes & fees
10 May - 11 May
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, (1,001 reviews)
"Breakfast was awesome, I recommend the Cinnamon French Toast."
United States
Walter
The price is ฿4,404
฿6,358 total
includes taxes & fees
30 Apr - 1 May
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, (447 reviews)
"Nice place, easy check in"
United States
Robert
The price is ฿3,509
฿3,850 total
includes taxes & fees
5 May - 6 May
Shaker Mill Inn

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (556 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. "
United States
SUSAN
The price is ฿3,541
฿3,956 total
includes taxes & fees
29 Apr - 30 Apr
The Little Lion

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 IHG
3.5 star property
6.6 km from Chesterwood
9.0 out of 10, Wonderful, (885 reviews)
"Great place for a family vacation. Lots of activities for kids and peaceful location in the Berkshires. "
United States
Khary
The price is ฿3,622
฿4,675 total
includes taxes & fees
30 Apr - 1 May
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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, (758 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"
United States
Berdest
The price is ฿3,574
฿3,992 total
includes taxes & fees
4 May - 5 May
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, (778 reviews)
"Staff made our stay enjoyable. Very friendly and extremely helpful. Wanted to check in earlier then normal. They were very helpful. Breakfast was normal chain breakfast. Very quiet hotel."
United States
Graham
The price is ฿4,894
฿5,466 total
includes taxes & fees
3 May - 4 May
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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
9.0 out of 10, Wonderful, (1,001 reviews)
"Beautiful place- beautiful views "
United States
Yanis
The price is ฿3,694
฿4,127 total
includes taxes & fees
19 May - 20 May
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Granville House

Granville House
3.0 star property
6.4 km from Chesterwood
10.0 out of 10, Exceptional, (100 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. "
United States
Nicole
The price is ฿6,439
฿7,192 total
includes taxes & fees
3 May - 4 May
Granville House

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (845 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is ฿2,202
฿2,460 total
includes taxes & fees
4 May - 5 May
Monument Mountain Motel

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 ฿8,461
฿9,923 total
includes taxes & fees
4 May - 5 May
The Inn at Stockbridge

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 ฿8,660
฿9,674 total
includes taxes & fees
28 Apr - 29 Apr
Devonfield Inn B&B

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 ฿5,505
฿6,149 total
includes taxes & fees
27 May - 28 May
Chambery Inn

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
9.1 km from Chesterwood
8.4 out of 10, Very good, (1,001 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is ฿3,448
฿3,852 total
includes taxes & fees
17 May - 18 May
Quality Inn Lee - Lenox South

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, (576 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is ฿2,415
฿2,697 total
includes taxes & fees
28 Apr - 29 Apr
Travelodge by Wyndham Great Barrington Berkshires

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,002 reviews)
"Great staff, great breakfast, clean facilities, quiet, good location"
United States
Chris
The price is ฿4,425
฿5,091 total
includes taxes & fees
28 Apr - 29 Apr
The Cornell Inn, Lenox & The Berkshires

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 ฿2,289
฿2,511 total
includes taxes & fees
28 Apr - 29 Apr
Pleasant Valley Motel West Stockbridge

Berkshires Untold

Berkshires Untold
3.5 star property
13 km from Chesterwood
9.0 out of 10, Wonderful, (917 reviews)
"Such a cool and affordable place to stay in the Berkshires. Great lobby/bar with a good restaurant."
United States
Kathy
The price is ฿2,758
฿3,081 total
includes taxes & fees
30 Apr - 1 May
Berkshires Untold

East Rock Inn

East Rock Inn
2.0 star property
10.1 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."
United States
Laura
The price is ฿4,543
฿5,075 total
includes taxes & fees
28 Apr - 29 Apr
East Rock Inn

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (293 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 ฿4,462
฿4,983 total
includes taxes & fees
29 Apr - 30 Apr
The Whitlock
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
111 reviews
View
Exterior
The Red Lion Inn
3.5 star property
8.8
Excellent
1,001 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
447 reviews
View
Exterior
The Little Lion
3.0 star property
8.6
Excellent
556 reviews
View
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.0
Wonderful
885 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, take a look at the 10 hotels and other accommodation options you'll find within a mile.
Where is the best place 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 traveller 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 will I find near Chesterwood?
Expedia has 10 hotels and other accommodation options within a mile from Chesterwood.
If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?
Yes! You'll find that most room reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to get the best options available near Chesterwood.
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.