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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 ¥48,655
¥58,859 total
includes taxes & fees
Feb 21 - Feb 22
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, (1,002 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is ¥23,999
¥33,831 total
includes taxes & fees
Mar 3 - Mar 4
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, (445 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is ¥18,211
¥19,977 total
includes taxes & fees
Feb 9 - Feb 10
Shaker Mill Inn

Granville House

Granville House
3.0 star property
6.4 km from Chesterwood
10.0 out of 10, Exceptional, (93 reviews)
"Absolutely magical at Christmas time! It was only for a quick overnight but felt like time stood still while we were there. The service was impeccable and Terry and Terri were a delight! I look forward to returning. "
United States
Jennifer
The price is ¥27,356
¥30,557 total
includes taxes & fees
Feb 9 - Feb 10
Granville House

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 ¥37,544
¥44,034 total
includes taxes & fees
Feb 22 - Feb 23
The Inn at Stockbridge

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, (832 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is ¥16,555
¥21,566 total
includes taxes & fees
Mar 1 - Mar 2
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, (731 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is ¥16,823
¥18,791 total
includes taxes & fees
Feb 22 - Feb 23
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
2.5 star property
8.6 km from Chesterwood
9.4 out of 10, Exceptional, (766 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is ¥23,740
¥26,517 total
includes taxes & fees
Feb 12 - Feb 13
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (553 reviews)
"Great friendly staff"
United States
Pablo
The price is ¥17,294
¥19,317 total
includes taxes & fees
Feb 9 - Feb 10
The Little Lion

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (135 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B

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, (1,002 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is ¥15,368
¥17,167 total
includes taxes & fees
Mar 1 - Mar 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (819 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (374 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
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, (1,000 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is ¥13,230
¥14,778 total
includes taxes & fees
Feb 22 - Feb 23
Quality Inn Lee - Lenox South

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 ¥9,197
¥10,089 total
includes taxes & fees
Feb 10 - Feb 11
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, (567 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is ¥11,792
¥13,172 total
includes taxes & fees
Feb 9 - Feb 10
Travelodge by Wyndham Great Barrington Berkshires

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.6 out of 10, Exceptional, (37 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is ¥19,117
¥21,353 total
includes taxes & fees
Feb 22 - Feb 23
East Rock 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, (18 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is ¥21,854
¥24,410 total
includes taxes & fees
Feb 22 - Feb 23
Element Lenox Berkshires

33 Main

33 Main
4.0 star property
9.8 km from Chesterwood
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is ¥63,136
¥70,523 total
includes taxes & fees
Mar 11 - Mar 12
33 Main
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
Star rating
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
1,002 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
445 reviews
View
Individually decorated, individually furnished, desk, laptop workspace
Granville House
3.0 star property
10.0
Exceptional
93 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 Charles H. Baldwin & Sons while you're out sightseeing near Chesterwood.