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9 Dec - 10 Dec
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Our top choices for Chesterwood hotels

2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets
Tanglewood Suites

Tanglewood Suites

2.5 star property
2.6 km from Chesterwood
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
The price is 5.773.278 ₫
5.773.278 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Tanglewood Suites
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1001)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is 3.980.662 ₫
5.624.333 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
The Red Lion Inn
Exterior
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 6.611.590 ₫
7.754.647 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
The Inn at Stockbridge
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is 2.873.458 ₫
3.152.183 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Shaker Mill Inn
Exterior
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, (707)
"Great hospitality "
United States
regina maria
The price is 2.688.924 ₫
3.003.527 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Property amenity
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, (797)
"Place was great!"
United States
Benjamin
The price is 2.702.369 ₫
3.533.923 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lobby
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, (758)
"Clean room, very courteous staff "
United States
Thomas
The price is 3.347.974 ₫
3.739.686 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior
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)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is 2.667.834 ₫
2.979.971 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (547)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is 2.900.700 ₫
3.240.082 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
The Little Lion
Front of property – evening/night
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
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (804)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2.0 star property
4.7 km from Chesterwood
6.8 out of 10, (1002)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is 1.399.822 ₫
1.535.605 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Pleasant Valley Motel West Stockbridge
Front of property
Chambery Inn

Chambery Inn

3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Lobby
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, (1002)
"Clean room and good breakfast "
United States
Kelly
The price is 2.386.552 ₫
2.665.778 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Lee - Lenox South
In-room safe, desk, free cots/infant beds, free rollaway beds
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, (562)
"The staff were very friendly and accommodating "
United States
Tom
The price is 1.977.150 ₫
2.208.608 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Travelodge by Wyndham Great Barrington Berkshires
Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, rollaway beds, free WiFi
Brook Farm Inn

Brook Farm Inn

3.5 star property
9.1 km from Chesterwood
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
12.5 km from Chesterwood
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is 3.453.422 ₫
3.857.473 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Element Lenox Berkshires
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (650)
"The room was clean and the service adequate"
United States
David
The price is 1.658.170 ₫
1.852.176 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Econo Lodge Lee - Great Barrington
Property amenity
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, (589)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is 3.558.870 ₫
3.975.257 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Courtyard by Marriott Lenox Berkshires
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Private kitchen | Mini-fridge, microwave, electric kettle
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 3.653.061 ₫
4.080.469 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
East Rock Inn
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.
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Top Chesterwood Hotel Reviews

Hotels near other Chesterwood attractions

Norman Rockwell Museum

4.7/5 (252 reviews)
You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.
See properties

Berkshire Botanical Garden

4.0/5 (1 review)
Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.
See properties

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.
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.

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