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
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Chesterwood

Business centre
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 ₹34,364
₹41,570 total
includes taxes & fees
28 Dec - 29 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and 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 ₹19,705
₹19,705 total
includes taxes & fees
7 Dec - 8 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, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is ₹11,404
₹16,768 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Red Lion Inn
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 ₹9,611
₹10,544 total
includes taxes & fees
8 Dec - 9 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, (703)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
The price is ₹9,627
₹10,754 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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
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 ₹23,646
₹27,733 total
includes taxes & fees
21 Dec - 22 Dec
The Inn at Stockbridge
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, (1002)
"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 ₹9,106
₹10,171 total
includes taxes & fees
15 Dec - 16 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (795)
"Place was great!"
United States
Benjamin
The price is ₹9,582
₹12,463 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 ₹9,897
₹11,055 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Little Lion
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 ₹13,586
₹15,176 total
includes taxes & fees
9 Dec - 10 Dec
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (289)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is ₹16,746
₹19,641 total
includes taxes & fees
12 Dec - 13 Dec
Lakehouse Inn
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

Quality Inn

2.5 star property
9.2 km from Chesterwood
8.4 out of 10, Very good, (1000)
"Clean room and good breakfast "
United States
Kelly
The price is ₹8,153
₹9,107 total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn
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 ₹4,683
₹5,137 total
includes taxes & fees
1 Jan - 2 Jan 2026
Pleasant Valley Motel West Stockbridge
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 ₹6,748
₹7,538 total
includes taxes & fees
7 Dec - 8 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 ₹11,787
₹13,166 total
includes taxes & fees
14 Dec - 15 Dec
Element Lenox Berkshires
Exterior
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)
"Great stay!"
United States
Ann
The price is ₹8,030
₹8,970 total
includes taxes & fees
21 Dec - 22 Dec
The Yankee, Trademark Collection by Wyndham
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

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

10/10 Excellent
"Quite , clean , very good all around."
Psul 1-night trip
Posted 3 days ago
Pleasant Valley Motel West Stockbridge

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.
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. Other good choices within a few miles include The Red Lion Inn and Tanglewood Suites.
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