Top Hotels Near Chesterwood in South Lee from AU$101

  • 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
16 Feb - 17 Feb
Tomorrow
17 Feb - 18 Feb
This weekend
20 Feb - 22 Feb
Next weekend
27 Feb - 1 Mar

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chesterwood hotels

Suite, Private Bathroom (RedBird Suite) | View from room

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 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is AU$529
includes taxes & fees
1 Mar - 2 Mar
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is AU$152
includes taxes & fees
2 Mar - 3 Mar
Shaker Mill Inn
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,000 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is AU$293
includes taxes & fees
11 Mar - 12 Mar
The Red Lion 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, (733 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is AU$169
includes taxes & fees
22 Feb - 23 Feb
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, (838 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is AU$205
includes taxes & fees
22 Feb - 23 Feb
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior

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, (767 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is AU$238
includes taxes & fees
22 Feb - 23 Feb
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (553 reviews)
"Great friendly staff"
United States
Pablo
The price is AU$174
includes taxes & fees
17 Feb - 18 Feb
The Little Lion
Room, 2 Queen Beds, Non Smoking

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (822 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel
Lake

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, (1,000 reviews)
"Clean room, nice staff , decent breakfast. Overall a good stay . "
United States
Anindita
The price is AU$154
includes taxes & fees
8 Mar - 9 Mar
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Room #10 Queen's Cottage | Living room

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (135 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
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, (1,003 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is AU$133
includes taxes & fees
1 Mar - 2 Mar
Quality Inn Lee - Lenox South
Front of property

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (375 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.8 out of 10, Exceptional, (18 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is AU$220
includes taxes & fees
22 Feb - 23 Feb
Element Lenox Berkshires
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, (569 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is AU$118
includes taxes & fees
22 Feb - 23 Feb
Travelodge by Wyndham Great Barrington Berkshires
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
9.1 km from Chesterwood
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.6 out of 10, Exceptional, (37 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is AU$204
includes taxes & fees
6 Mar - 7 Mar
East Rock Inn
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, (601 reviews)
"Our stay was great! "
United States
Gianna
The price is AU$199
includes taxes & fees
15 Mar - 16 Mar
Courtyard by Marriott Lenox Berkshires
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
7.4 km from Chesterwood
6.4 out of 10, (658 reviews)
"The room was clean and the service adequate"
United States
David
The price is AU$101
includes taxes & fees
1 Mar - 2 Mar
Econo Lodge Lee - Great Barrington
Exterior

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (288 reviews)
"Super cute place and walking distance to a bunch of great shops and food! "
United States
Gina
The price is AU$188
includes taxes & fees
18 Feb - 19 Feb
The Whitlock
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
13 km from Chesterwood
9.0 out of 10, Wonderful, (856 reviews)
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
United States
Melissa
The price is AU$191
includes taxes & fees
19 Feb - 20 Feb
Berkshires Untold
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

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
110 reviews
View
Garden
Shaker Mill Inn
2.5 star property
9.6
Exceptional
446 reviews
View
Exterior
The Red Lion Inn
3.5 star property
8.8
Excellent
1,000 reviews
View
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8
Excellent
733 reviews
View
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.0
Wonderful
838 reviews
View

Top Chesterwood Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great stay. The only thing I would say - and I’ve been staying at the hotel since the 80s - it might be time for a few updates here and there. It runs the risk of going from rustic charm to grandma’s house in the not tooooo distant future. "
Simon 1-night trip
Posted 3 weeks ago
The Red Lion Inn

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. 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.