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Our top choices for Chesterwood hotels

The Red Lion Inn

The Red Lion Inn
3.5 star property
2.1 mi from Chesterwood
8.8 out of 10, Excellent, (1,010 reviews)
"a delightful inn centrally located in charming Stockbridge"
United States
molly
The price is £151
includes taxes & fees
19 May - 20 May
The Red Lion Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
3.6 mi from Chesterwood
9.6 out of 10, Exceptional, (454 reviews)
"Everything was excellent"
United States
Barbara
The price is £98
includes taxes & fees
26 May - 27 May
Shaker Mill Inn

The Little Lion

The Little Lion
3.0 star property
3.2 mi from Chesterwood
8.6 out of 10, Excellent, (559 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 £78
includes taxes & fees
11 Jun - 12 Jun
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
4.1 mi from Chesterwood
9.2 out of 10, Wonderful, (894 reviews)
"Family friendly resort with amenities the whole family can enjoy!"
United States
Justina
The price is £120
includes taxes & fees
18 May - 19 May
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
5.4 mi from Chesterwood
9.0 out of 10, Wonderful, (852 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is £56
includes taxes & fees
21 May - 22 May
Monument Mountain Motel

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
3.2 mi from Chesterwood
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is £228
includes taxes & fees
25 May - 26 May
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
5 mi from Chesterwood
8.8 out of 10, Excellent, (764 reviews)
"Above average hotel breakfast. Very clean hotel."
United States
Helen
The price is £102
includes taxes & fees
27 May - 28 May
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
5.3 mi from Chesterwood
9.0 out of 10, Wonderful, (1,000 reviews)
"Nice location. Can rent their pontoon boat."
United States
Paul
The price is £105
includes taxes & fees
17 May - 18 May
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Chambery Inn

Chambery Inn
3.0 star property
5.4 mi 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 £141
includes taxes & fees
20 May - 21 May
Chambery Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
4.7 mi from Chesterwood
10.0 out of 10, Exceptional, (138 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is £222
includes taxes & fees
18 May - 19 May
Devonfield Inn B&B

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
5.3 mi from Chesterwood
9.4 out of 10, Exceptional, (780 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is £161
includes taxes & fees
31 May - 1 Jun
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
3.8 mi from Chesterwood
7.6 out of 10, Good, (578 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is £62
includes taxes & fees
26 May - 27 May
Travelodge by Wyndham Great Barrington Berkshires

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
2.9 mi from Chesterwood
6.8 out of 10, (1,000 reviews)
"Rooms need an update badly."
United States
john
The price is £49
includes taxes & fees
26 May - 27 May
Pleasant Valley Motel West Stockbridge

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
6.4 mi from Chesterwood
8.4 out of 10, Very good, (1,000 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is £70
includes taxes & fees
17 May - 18 May
Quality Inn Great Barrington

East Rock Inn

East Rock Inn
2.0 star property
6.3 mi 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 £115
includes taxes & fees
18 May - 19 May
East Rock Inn

Brook Farm Inn

Brook Farm Inn
3.5 star property
5.7 mi from Chesterwood
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
The price is £157
includes taxes & fees
3 Jun - 4 Jun
Brook Farm Inn

The Whitlock

The Whitlock
2.0 star property
6.1 mi from Chesterwood
8.6 out of 10, Excellent, (299 reviews)
"Nice rooms, great location."
United States
Rick
The price is £95
includes taxes & fees
18 May - 19 May
The Whitlock

Berkshires Untold

Berkshires Untold
3.5 star property
8.1 mi from Chesterwood
9.0 out of 10, Wonderful, (941 reviews)
"Great stay!"
United States
Aditya
The price is £83
includes taxes & fees
28 May - 29 May
Berkshires Untold

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
7.8 mi from Chesterwood
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is £131
includes taxes & fees
28 May - 29 May
Element Lenox Berkshires

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
4.6 mi from Chesterwood
6.4 out of 10, (663 reviews)
"Good to stay. "
United States
Ibinabo
The price is £53
includes taxes & fees
28 May - 29 May
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.

Compare popular hotels close to Chesterwood

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Exterior
The Red Lion Inn
3.5 star property
8.8
Excellent
1,010 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
454 reviews
View
Exterior
The Little Lion
3.0 star property
8.6
Excellent
559 reviews
View
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.2
Wonderful
894 reviews
View
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
2.5 star property
9.0
Wonderful
852 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.