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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)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is Rp5.896.836
Rp7.133.461 total
includes taxes & fees
29 Jun - 30 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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, (785 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is Rp3.476.449
Rp3.883.194 total
includes taxes & fees
1 Jul - 2 Jul
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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, (772 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is Rp2.446.820
Rp2.733.116 total
includes taxes & fees
23 Jun - 24 Jun
Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,006 reviews)
"a delightful inn centrally located in charming Stockbridge"
United States
molly
The price is Rp2.743.296
Rp3.862.246 total
includes taxes & fees
22 Jun - 23 Jun
The Red Lion Inn

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
10.3 km from Chesterwood
8.6 out of 10, Excellent, (1,001 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is Rp1.679.733
Rp1.876.193 total
includes taxes & fees
17 Jun - 18 Jun
Quality Inn Great Barrington

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.4 out of 10, Exceptional, (48 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 Rp2.592.736
Rp2.896.086 total
includes taxes & fees
13 Jul - 14 Jul
East Rock Inn

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, (583 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 Rp1.410.940
Rp1.576.020 total
includes taxes & fees
15 Jun - 16 Jun
Travelodge by Wyndham Great Barrington Berkshires

Little Cat Lodge

Little Cat Lodge
2.0 star property
16.3 km from Chesterwood
9.6 out of 10, Exceptional, (81 reviews)
"Excellent lodge, recommend."
United States
Jason
The price is Rp2.716.506
Rp3.042.486 total
includes taxes & fees
21 Jun - 22 Jun
Little Cat Lodge

The Yankee Inn

The Yankee Inn
2.5 star property
14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,013 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is Rp1.871.728
Rp2.090.692 total
includes taxes & fees
15 Jun - 16 Jun
The Yankee Inn

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (307 reviews)
"A beautiful old inn in the heart of a lovely old town."
United States
Linda
The price is Rp2.767.943
Rp3.091.792 total
includes taxes & fees
25 Jun - 26 Jun
The Whitlock

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (666 reviews)
"Decent place.friendly, quiet"
United States
William
The price is Rp1.351.109
Rp1.509.189 total
includes taxes & fees
29 Jun - 30 Jun
Econo Lodge Lee - Great Barrington

Prospect Berkshires

Prospect Berkshires
3.0 star property
12.8 km from Chesterwood
9.8 out of 10, Exceptional, (29 reviews)
"Great stay!"
United States
Conor
The price is Rp5.867.010
Rp7.151.858 total
includes taxes & fees
6 Jul - 7 Jul
Prospect Berkshires

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
9.7 km from Chesterwood
5.4 out of 10, (469 reviews)
"The breakfast was not diabetic friendly. They stated pet friendly but no place for dog to go to the bathroom. Had to walk dog through garbage . Cigarette butts all over very the place. Beds were terrible. My towels had clumps of black hair on them. Lotion and shampoos left in room were used not new ones. Will not go back"
United States
Stacy
The price is Rp1.173.223
Rp1.314.139 total
includes taxes & fees
15 Jun - 16 Jun
Berkshire Travel Lodge

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, (1,003 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is Rp2.980.477
Rp3.429.067 total
includes taxes & fees
16 Jun - 17 Jun
The Cornell Inn, Lenox & The Berkshires

Berkshires Untold

Berkshires Untold
3.5 star property
13 km from Chesterwood
9.0 out of 10, Wonderful, (986 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
The price is Rp2.430.353
Rp2.714.704 total
includes taxes & fees
15 Jun - 16 Jun
Berkshires Untold

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
16.9 km from Chesterwood
8.6 out of 10, Excellent, (1,001 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is Rp2.057.472
Rp2.298.197 total
includes taxes & fees
16 Jun - 17 Jun
Best Western Plus Berkshire Hills Inn & Suites

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
17.5 km from Chesterwood
9.8 out of 10, Exceptional, (107 reviews)
"Very nice hotel."
United States
Erdem
The price is Rp2.839.740
Rp3.180.509 total
includes taxes & fees
17 Jun - 18 Jun
Inn at Silver Maple Farm

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
15.5 km from Chesterwood
9.4 out of 10, Exceptional, (106 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
The price is Rp2.500.400
Rp2.792.947 total
includes taxes & fees
22 Jun - 23 Jun
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
19.9 km from Chesterwood
9.8 out of 10, Exceptional, (53 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is Rp3.443.051
Rp3.845.972 total
includes taxes & fees
22 Jun - 23 Jun
Wilder House Berkshires

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
14.9 km from Chesterwood
7.6 out of 10, Good, (867 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is Rp1.410.940
Rp1.576.020 total
includes taxes & fees
15 Jun - 16 Jun
Howard Johnson by Wyndham Lenox
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
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
9.4
Exceptional
785 reviews
View
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8
Excellent
772 reviews
View
Exterior
The Red Lion Inn
3.5 star property
8.8
Excellent
1,006 reviews
View
Lobby
Quality Inn Great Barrington
2.5 star property
8.6
Excellent
1,001 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.