Hotels near Chesterwood

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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 RM1,309
RM1,584 total
includes taxes & fees
14 Jun - 15 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, (1,001 reviews)
"a delightful inn centrally located in charming Stockbridge"
United States
molly
The price is RM674
RM930 total
includes taxes & fees
9 Jun - 10 Jun
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, (562 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is RM393
RM438 total
includes taxes & fees
3 Jun - 4 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
6.6 km from Chesterwood
9.2 out of 10, Wonderful, (904 reviews)
"Wonderful stay for families."
United States
Kimberly
The price is RM496
RM632 total
includes taxes & fees
9 Jun - 10 Jun
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (457 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is RM591
RM648 total
includes taxes & fees
2 Jun - 3 Jun
Shaker Mill Inn

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (859 reviews)
"This is a great choice for folks traveling on a budget. Clean rooms, friendly owners, and nice retro vibe. Will be staying here again on my trips through the Berkshires."
United States
Mark
The price is RM305
RM341 total
includes taxes & fees
7 Jun - 8 Jun
Monument Mountain Motel

Granville House

Granville House
3.0 star property
6.4 km from Chesterwood
10.0 out of 10, Exceptional, (101 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 RM793
RM886 total
includes taxes & fees
2 Jun - 3 Jun
Granville House

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, (767 reviews)
"Above average hotel breakfast. Very clean hotel."
United States
Helen
The price is RM539
RM602 total
includes taxes & fees
9 Jun - 10 Jun
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
8.6 km from Chesterwood
9.0 out of 10, Wonderful, (1,001 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 RM520
RM581 total
includes taxes & fees
4 Jun - 5 Jun
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (377 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 RM678
RM757 total
includes taxes & fees
3 Jun - 4 Jun
Chambery 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, (581 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 RM313
RM350 total
includes taxes & fees
2 Jun - 3 Jun
Travelodge by Wyndham Great Barrington Berkshires

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, (1,002 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is RM448
RM501 total
includes taxes & fees
4 Jun - 5 Jun
Quality Inn Lee - Lenox South

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, (782 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is RM772
RM862 total
includes taxes & fees
8 Jun - 9 Jun
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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 RM1,304
RM1,457 total
includes taxes & fees
4 Jun - 5 Jun
Devonfield Inn B&B

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 RM285
RM313 total
includes taxes & fees
2 Jun - 3 Jun
Pleasant Valley Motel West Stockbridge

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, (1,001 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is RM617
RM710 total
includes taxes & fees
9 Jun - 10 Jun
The Cornell Inn, Lenox & The Berkshires

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.4 out of 10, Exceptional, (47 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 RM624
RM697 total
includes taxes & fees
14 Jun - 15 Jun
East Rock Inn

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (302 reviews)
"A beautiful old inn in the heart of a lovely old town."
United States
Linda
The price is RM494
RM552 total
includes taxes & fees
3 Jun - 4 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, (664 reviews)
"Decent place.friendly, quiet"
United States
William
The price is RM282
RM315 total
includes taxes & fees
8 Jun - 9 Jun
Econo Lodge Lee - Great Barrington

Berkshires Untold

Berkshires Untold
3.5 star property
13 km from Chesterwood
9.0 out of 10, Wonderful, (966 reviews)
"Friendly good location"
United States
Vivian
The price is RM495
RM553 total
includes taxes & fees
3 Jun - 4 Jun
Berkshires Untold
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
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
1,001 reviews
View
Exterior
The Little Lion
3.0 star property
8.6
Excellent
562 reviews
View
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.2
Wonderful
904 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
457 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.