Find hotels near Chesterwood, South Lee from NT$2,203

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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 NT$10,358
NT$12,530 total
includes taxes & fees
Jun 16 - Jun 17
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, (1,002 reviews)
"a delightful inn centrally located in charming Stockbridge"
United States
molly
The price is NT$4,756
NT$6,718 total
includes taxes & fees
Jun 16 - Jun 17
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 NT$2,761
NT$3,084 total
includes taxes & fees
Jun 4 - Jun 5
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 NT$3,642
NT$4,682 total
includes taxes & fees
Jun 21 - Jun 22
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, (458 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is NT$5,176
NT$5,678 total
includes taxes & fees
Jun 7 - Jun 8
Shaker Mill Inn

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (860 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 NT$2,414
NT$2,697 total
includes taxes & fees
Jun 4 - Jun 5
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 NT$6,274
NT$7,009 total
includes taxes & fees
Jun 4 - Jun 5
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, (768 reviews)
"Spotless, clean, comfortable, friendly staff."
United States
cynthia
The price is NT$4,423
NT$4,941 total
includes taxes & fees
Jun 21 - Jun 22
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)
"Clean rooms and lovely view"
Canada
Laraib
The price is NT$4,004
NT$4,473 total
includes taxes & fees
Jun 7 - Jun 8
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, (782 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is NT$6,123
NT$6,839 total
includes taxes & fees
Jun 11 - Jun 12
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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 NT$5,364
NT$5,992 total
includes taxes & fees
Jun 7 - Jun 8
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 NT$2,478
NT$2,768 total
includes taxes & fees
Jun 4 - Jun 5
Travelodge by Wyndham Great Barrington Berkshires

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 NT$2,951
NT$3,296 total
includes taxes & fees
Jun 7 - Jun 8
Quality Inn Great Barrington

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 NT$10,635
NT$11,879 total
includes taxes & fees
Jun 8 - Jun 9
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, (1,002 reviews)
"The property is in terrible condition."
United States
Olga V
The price is NT$2,008
NT$2,203 total
includes taxes & fees
Jun 4 - Jun 5
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, (1,000 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is NT$5,235
NT$6,023 total
includes taxes & fees
Jun 11 - Jun 12
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 NT$4,443
NT$4,963 total
includes taxes & fees
Jun 18 - Jun 19
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 NT$4,862
NT$5,431 total
includes taxes & fees
Jun 18 - Jun 19
The Whitlock

The Yankee Inn

The Yankee Inn
2.5 star property
14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,002 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is NT$3,498
NT$3,907 total
includes taxes & fees
Jun 17 - Jun 18
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, (665 reviews)
"Decent place.friendly, quiet"
United States
William
The price is NT$2,236
NT$2,498 total
includes taxes & fees
Jun 11 - Jun 12
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
1,002 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
458 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.

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