South Lee Chesterwood Hotels

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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, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is HK$2,968
HK$3,590 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
5.2 km from Chesterwood
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is HK$1,949
HK$2,286 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Inn at Stockbridge

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
12.1 km from Chesterwood
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is HK$4,469
HK$4,902 total
includes taxes & fees
28 Dec - 29 Dec
Inn at Kenmore Hall

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (374)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
8.6 km from Chesterwood
9.4 out of 10, Exceptional, (759)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is HK$1,049
HK$1,172 total
includes taxes & fees
14 Jan - 15 Jan 2026
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is HK$1,050
HK$1,173 total
includes taxes & fees
4 Jan - 5 Jan 2026
Element Lenox Berkshires

Brook Farm Inn

Brook Farm Inn
3.5 star property
9.1 km from Chesterwood
9.4 out of 10, Exceptional, (164)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn

Prospect Berkshires

Prospect Berkshires
3.0 star property
12.8 km from Chesterwood
9.6 out of 10, Exceptional, (17)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is HK$1,960
HK$2,449 total
includes taxes & fees
26 Jan - 27 Jan 2026
Prospect Berkshires

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
17.5 km from Chesterwood
9.8 out of 10, Exceptional, (98)
"Great stay, comfortable place"
United States
barry
The price is HK$1,003
HK$1,123 total
includes taxes & fees
4 Jan - 5 Jan 2026
Inn at Silver Maple Farm

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.4 out of 10, Exceptional, (36)
"We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again."
United States
Laura
The price is HK$959
HK$1,072 total
includes taxes & fees
13 Jan - 14 Jan 2026
East Rock Inn

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
9.0 out of 10, Wonderful, (808)
"Convenient location, very roomy, well equipped kitchen. "
United States
Carolyn
The price is HK$994
HK$1,262 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1001)
"Old time charm and hot tub under the stars"
United States
Lori
The price is HK$1,107
HK$1,584 total
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
19.9 km from Chesterwood
9.8 out of 10, Exceptional, (41)
"The place is lovely, room is cozy, and the bed is comfy"
United States
Mark
The price is HK$1,259
HK$1,406 total
includes taxes & fees
30 Dec - 31 Dec
Wilder House Berkshires

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, (1000)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is HK$807
HK$901 total
includes taxes & fees
12 Jan - 13 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (810)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
12.1 km from Chesterwood
9.2 out of 10, Wonderful, (592)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is HK$1,080
HK$1,207 total
includes taxes & fees
6 Jan - 7 Jan 2026
Courtyard by Marriott Lenox Berkshires

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1000)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is HK$720
HK$805 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Yankee, Trademark Collection by Wyndham

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
14.7 km from Chesterwood
9.2 out of 10, Wonderful, (1002)
"Very comfortable beds! "
United States
Gerald
The price is HK$802
HK$896 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Berkshires-Lenox

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, (711)
"Great hospitality "
United States
regina maria
The price is HK$832
HK$929 total
includes taxes & fees
14 Jan - 15 Jan 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.

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 Charles H. Baldwin & Sons while you're out sightseeing near Chesterwood.