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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, (112 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is ₩505,068
₩610,985 total
includes taxes & fees
Jul 21 - Jul 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, (1,005 reviews)
"Clean room and breakfast"
United States
Raphael
The price is ₩270,622
₩370,676 total
includes taxes & fees
Jul 22 - Jul 23
The Red Lion Inn

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (579 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is ₩171,435
₩191,493 total
includes taxes & fees
Jul 13 - Jul 14
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
9.2 out of 10, Wonderful, (927 reviews)
"Wonderful stay for families."
United States
Kimberly
The price is ₩253,479
₩313,060 total
includes taxes & fees
Jul 16 - Jul 17
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires 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, (792 reviews)
"Dawn was super helpful in getting us checked in."
United States
Kristen
The price is ₩323,966
₩361,870 total
includes taxes & fees
Jul 14 - Jul 15
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, (785 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is ₩252,561
₩282,118 total
includes taxes & fees
Jul 27 - Jul 28
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (876 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens) Loved the place."
United States
Yekaterina
The price is ₩170,028
₩189,930 total
includes taxes & fees
Jul 14 - Jul 15
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)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is ₩585,940
₩687,225 total
includes taxes & fees
Jul 20 - Jul 21
The Inn at Stockbridge

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ₩273,820
₩300,380 total
includes taxes & fees
Jul 8 - Jul 9
Shaker Mill Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is ₩671,547
₩750,113 total
includes taxes & fees
Jul 14 - Jul 15
Devonfield Inn B&B

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, (1,006 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is ₩218,903
₩244,515 total
includes taxes & fees
Jul 22 - Jul 23
Quality Inn Lee - Lenox South

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (380 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 ₩413,011
₩461,333 total
includes taxes & fees
Jul 14 - Jul 15
Chambery Inn

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.4 out of 10, Exceptional, (49 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 ₩237,214
₩264,968 total
includes taxes & fees
Jul 22 - Jul 23
East Rock Inn

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, (1,006 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is ₩331,203
₩381,053 total
includes taxes & fees
Jul 12 - Jul 13
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, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
The price is ₩112,893
₩123,844 total
includes taxes & fees
Jul 8 - Jul 9
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
7.4 out of 10, Good, (591 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 ₩151,442
₩169,161 total
includes taxes & fees
Jul 8 - Jul 9
Travelodge by Wyndham Great Barrington Berkshires

Berkshires Untold

Berkshires Untold
3.5 star property
13 km from Chesterwood
9.0 out of 10, Wonderful, (1,005 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
The price is ₩285,259
₩318,635 total
includes taxes & fees
Jul 30 - Jul 31
Berkshires Untold

The Yankee Inn

The Yankee Inn
2.5 star property
14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,004 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is ₩194,701
₩217,477 total
includes taxes & fees
Jul 8 - Jul 9
The Yankee Inn

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (674 reviews)
"Decent place.friendly, quiet"
United States
William
The price is ₩128,726
₩143,787 total
includes taxes & fees
Aug 3 - Aug 4
Econo Lodge Lee - Great Barrington

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.8 out of 10, Exceptional, (28 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is ₩350,306
₩391,291 total
includes taxes & fees
Jul 27 - Jul 28
Element by Marriott Lenox Berkshires
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
112 reviews
View
Exterior
The Red Lion Inn
3.5 star property
8.8
Excellent
1,005 reviews
View
Exterior
The Little Lion
3.0 star property
8.6
Excellent
579 reviews
View
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.2
Wonderful
927 reviews
View
Exterior
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
9.4
Exceptional
792 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 Lenox Arts Center while you're out sightseeing near Chesterwood.