Search Hotels Near Chesterwood, South Lee

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Chesterwood

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 5.773.497 ₫
5.773.497 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Tanglewood Suites
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

3.0 star property
6.4 km from Chesterwood
10.0 out of 10, Exceptional, (88)
"Outstanding all around!"
United States
Jonathan
The price is 5.272.600 ₫
5.889.494 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Granville House
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
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 6.928.196 ₫
8.125.867 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Inn at Stockbridge
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

4.0 star property
9.8 km from Chesterwood
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is 12.364.247 ₫
13.810.785 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
33 Main
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 2.873.567 ₫
3.152.304 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Shaker Mill 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 3.453.553 ₫
3.857.619 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Element Lenox Berkshires
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
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, (757)
"Clean room, very courteous staff "
United States
Thomas
The price is 3.348.101 ₫
3.739.829 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Aerial view
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 3.400.827 ₫
3.808.926 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Inn at Silver Maple Farm
Egyptian cotton sheets, premium bedding, down duvets, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
12.8 km from Chesterwood
9.6 out of 10, Exceptional, (15)
"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 6.854.380 ₫
8.539.767 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Prospect Berkshires
Lobby
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 11.204.275 ₫
12.291.221 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Inn at Kenmore Hall
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 3.653.200 ₫
4.080.625 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
East Rock Inn
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
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
Wilder House Berkshires

Wilder House Berkshires

2.0 star property
19.9 km from Chesterwood
9.8 out of 10, Exceptional, (38)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
The price is 4.270.806 ₫
4.770.490 ₫ total
includes taxes & fees
9 Dec - 10 Dec
Wilder House Berkshires
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, (796)
"Place was great!"
United States
Benjamin
The price is 3.532.642 ₫
4.461.359 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is 4.033.539 ₫
5.683.335 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
The Red Lion Inn
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, (1003)
"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 2.667.936 ₫
2.980.085 ₫ total
includes taxes & fees
17 Dec - 18 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (803)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
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, (588)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is 3.559.005 ₫
3.975.409 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Courtyard by Marriott Lenox Berkshires
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.
View all properties

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.

Explore a world of travel with Expedia