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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
0.4 mi 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 £303
includes taxes & fees
12 Jul - 13 Jul
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
2.1 mi from Chesterwood
8.8 out of 10, Excellent, (1,003 reviews)
"Clean room and breakfast"
United States
Raphael
The price is £164
includes taxes & fees
6 Jul - 7 Jul
The Red Lion Inn

The Little Lion

The Little Lion
3.0 star property
3.2 mi from Chesterwood
8.6 out of 10, Excellent, (572 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is £102
includes taxes & fees
7 Jul - 8 Jul
The Little Lion

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
3.6 mi from Chesterwood
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is £140
includes taxes & fees
1 Jul - 2 Jul
Shaker Mill Inn

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, (780 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is £126
includes taxes & fees
5 Jul - 6 Jul
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
5.4 mi from Chesterwood
9.0 out of 10, Wonderful, (875 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 £94
includes taxes & fees
5 Jul - 6 Jul
Monument Mountain Motel

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, (789 reviews)
"Dawn was super helpful in getting us checked in."
United States
Kristen
The price is £179
includes taxes & fees
14 Jul - 15 Jul
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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, (916 reviews)
"Wonderful stay for families."
United States
Kimberly
The price is £153
includes taxes & fees
29 Jul - 30 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Whitlock

The Whitlock
2.0 star property
6.1 mi from Chesterwood
8.6 out of 10, Excellent, (313 reviews)
"A beautiful old inn in the heart of a lovely old town."
United States
Linda
The price is £131
includes taxes & fees
12 Jul - 13 Jul
The Whitlock

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)
"The property is in terrible condition."
United States
Olga V
The price is £63
includes taxes & fees
29 Jun - 30 Jun
Pleasant Valley Motel West Stockbridge

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, (587 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 £75
includes taxes & fees
5 Jul - 6 Jul
Travelodge by Wyndham Great Barrington Berkshires

East Rock Inn

East Rock Inn
2.0 star property
6.3 mi 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 £115
includes taxes & fees
22 Jul - 23 Jul
East Rock Inn

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
6.4 mi from Chesterwood
8.6 out of 10, Excellent, (1,005 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is £112
includes taxes & fees
1 Jul - 2 Jul
Quality Inn Great Barrington

Chambery Inn

Chambery Inn
3.0 star property
5.4 mi 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 £228
includes taxes & fees
29 Jun - 30 Jun
Chambery Inn

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
6.7 mi from Chesterwood
9.2 out of 10, Wonderful, (1,002 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is £179
includes taxes & fees
1 Jul - 2 Jul
The Cornell Inn, Lenox & The 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, (669 reviews)
"Decent place.friendly, quiet"
United States
William
The price is £75
includes taxes & fees
6 Jul - 7 Jul
Econo Lodge Lee - Great Barrington

Berkshires Untold

Berkshires Untold
3.5 star property
8.1 mi from Chesterwood
9.0 out of 10, Wonderful, (991 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
The price is £148
includes taxes & fees
1 Jul - 2 Jul
Berkshires Untold

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
7.8 mi from Chesterwood
9.8 out of 10, Exceptional, (28 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is £186
includes taxes & fees
22 Jul - 23 Jul
Element by Marriott Lenox Berkshires

The Yankee Inn

The Yankee Inn
2.5 star property
9.3 mi from Chesterwood
9.2 out of 10, Wonderful, (1,003 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is £108
includes taxes & fees
6 Jul - 7 Jul
The Yankee Inn

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
6 mi from Chesterwood
8.0 out of 10, Very good, (10 reviews)
"Wonderful pet-friendly property in a fantastic location. Everything in the village is just a short walk away, making it easy to enjoy local shops, restaurants, and attractions."
United States
Leonardo
The price is £134
includes taxes & fees
30 Jun - 1 Jul
Hideaway Inn 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
The Red Lion Inn
3.5 star property
8.8
Excellent
1,003 reviews
View
Exterior
The Little Lion
3.0 star property
8.6
Excellent
572 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
462 reviews
View
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8
Excellent
780 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.