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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 8.099.139 ₫
9.797.846 ₫ total
includes taxes & fees
16 Mar - 17 Mar
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 4.403.802 ₫
6.083.240 ₫ total
includes taxes & fees
10 Mar - 11 Mar
The Red Lion Inn

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, (742 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is 2.788.206 ₫
3.114.427 ₫ total
includes taxes & fees
10 Mar - 11 Mar
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, (847 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is 3.142.595 ₫
4.019.712 ₫ total
includes taxes & fees
10 Mar - 11 Mar
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (554 reviews)
"Great friendly staff"
United States
Pablo
The price is 2.866.380 ₫
3.201.747 ₫ total
includes taxes & fees
4 Mar - 5 Mar
The Little Lion

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)
"Clean room, nice staff , decent breakfast. Overall a good stay . "
United States
Anindita
The price is 2.558.215 ₫
2.857.526 ₫ total
includes taxes & fees
23 Mar - 24 Mar
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (768 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is 3.977.992 ₫
4.443.417 ₫ total
includes taxes & fees
29 Mar - 30 Mar
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (824 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (136 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
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)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn

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
Brook Farm Inn

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.8 out of 10, Exceptional, (21 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is 3.622.062 ₫
4.045.844 ₫ total
includes taxes & fees
11 Mar - 12 Mar
Element Lenox Berkshires

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, (573 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is 1.954.350 ₫
2.183.139 ₫ total
includes taxes & fees
5 Mar - 6 Mar
Travelodge by Wyndham Great Barrington Berkshires

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)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is 2.424.743 ₫
2.708.437 ₫ total
includes taxes & fees
20 Mar - 21 Mar
Quality Inn Lee - Lenox South

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.6 out of 10, Exceptional, (38 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is 3.456.620 ₫
3.861.044 ₫ total
includes taxes & fees
22 Mar - 23 Mar
East Rock 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, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is 1.524.393 ₫
1.672.259 ₫ total
includes taxes & fees
10 Mar - 11 Mar
Pleasant Valley Motel West Stockbridge

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, (601 reviews)
"Our stay was great! "
United States
Gianna
The price is 3.622.062 ₫
4.045.844 ₫ total
includes taxes & fees
10 Mar - 11 Mar
Courtyard by Marriott Lenox Berkshires

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (290 reviews)
"Super cute place and walking distance to a bunch of great shops and food! "
United States
Gina
The price is 3.114.349 ₫
3.478.728 ₫ total
includes taxes & fees
4 Mar - 5 Mar
The Whitlock

Berkshires Untold

Berkshires Untold
3.5 star property
13 km from Chesterwood
9.0 out of 10, Wonderful, (866 reviews)
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
United States
Melissa
The price is 2.607.885 ₫
2.913.007 ₫ total
includes taxes & fees
5 Mar - 6 Mar
Berkshires Untold

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (658 reviews)
"The room was clean and the service adequate"
United States
David
The price is 1.574.971 ₫
1.759.243 ₫ total
includes taxes & fees
3 Apr - 4 Apr
Econo Lodge Lee - Great Barrington
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.

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.
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.