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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 ฿10,808
฿13,074 total
includes taxes & fees
29 Jun - 30 Jun
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, (1,009 reviews)
"Clean room and breakfast"
United States
Raphael
The price is ฿5,080
฿7,137 total
includes taxes & fees
1 Jul - 2 Jul
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, (461 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ฿5,368
฿5,889 total
includes taxes & fees
18 Jun - 19 Jun
Shaker Mill Inn

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (566 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is ฿2,881
฿3,218 total
includes taxes & fees
17 Jun - 18 Jun
The Little Lion

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 ฿4,485
฿5,009 total
includes taxes & fees
23 Jun - 24 Jun
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Granville House

Granville House
3.0 star property
6.4 km from Chesterwood
10.0 out of 10, Exceptional, (102 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is ฿7,332
฿8,190 total
includes taxes & fees
16 Jun - 17 Jun
Granville House

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, (909 reviews)
"Wonderful stay for families."
United States
Kimberly
The price is ฿4,390
฿5,543 total
includes taxes & fees
21 Jun - 22 Jun
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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, (1,005 reviews)
"Great breakfast and coffe is available 24 hours. Nice location to near by restaurants and great view by water."
United States
andrew
The price is ฿4,789
฿5,349 total
includes taxes & fees
22 Jun - 23 Jun
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, (786 reviews)
"Dawn was super helpful in getting us checked in."
United States
Kristen
The price is ฿6,093
฿6,806 total
includes taxes & fees
23 Jun - 24 Jun
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, (870 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 ฿2,519
฿2,814 total
includes taxes & fees
18 Jun - 19 Jun
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 ฿12,234
฿14,349 total
includes taxes & fees
23 Jun - 24 Jun
The Inn at Stockbridge

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 ฿11,097
฿12,395 total
includes taxes & fees
16 Jun - 17 Jun
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 ฿4,550
฿5,082 total
includes taxes & fees
17 Jun - 18 Jun
Quality Inn Lee - Lenox South

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, (584 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 ฿2,586
฿2,889 total
includes taxes & fees
16 Jun - 17 Jun
Travelodge by Wyndham Great Barrington 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, (1,002 reviews)
"The property is in terrible condition."
United States
Olga V
The price is ฿2,357
฿2,585 total
includes taxes & fees
16 Jun - 17 Jun
Pleasant Valley Motel West Stockbridge

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 ฿3,640
฿4,066 total
includes taxes & fees
21 Jun - 22 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 ฿5,073
฿5,667 total
includes taxes & fees
23 Jun - 24 Jun
The Whitlock

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 ฿5,280
฿5,898 total
includes taxes & fees
29 Jun - 30 Jun
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, (1,003 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is ฿5,463
฿6,285 total
includes taxes & fees
16 Jun - 17 Jun
The Cornell Inn, Lenox & The Berkshires

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (667 reviews)
"Decent place.friendly, quiet"
United States
William
The price is ฿2,476
฿2,766 total
includes taxes & fees
29 Jun - 30 Jun
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
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
The Red Lion Inn
3.5 star property
8.8
Excellent
1,009 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
461 reviews
View
Exterior
The Little Lion
3.0 star property
8.6
Excellent
566 reviews
View
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8
Excellent
772 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.