South Lee Hotel Guide - Chesterwood hotels in South Lee, United States of America.

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Check prices for these dates

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

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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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is €343
includes taxes & fees
9 Jun - 10 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,002 reviews)
"a delightful inn centrally located in charming Stockbridge"
United States
molly
The price is €202
includes taxes & fees
4 Jun - 5 Jun
The Red Lion Inn
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
9.2 out of 10, Wonderful, (902 reviews)
"Wonderful stay for families."
United States
Kimberly
The price is €128
includes taxes & fees
1 Jun - 2 Jun
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior

The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (562 reviews)
"Avoid this place."
United States
Carole
The price is €91
includes taxes & fees
11 Jun - 12 Jun
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, (857 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is €66
includes taxes & fees
31 May - 1 Jun
Monument Mountain Motel
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, (766 reviews)
"Above average hotel breakfast. Very clean hotel."
United States
Helen
The price is €127
includes taxes & fees
31 May - 1 Jun
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (457 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is €111
includes taxes & fees
27 May - 28 May
Shaker Mill Inn
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, (1,008 reviews)
"Clean rooms and lovely view"
Canada
Laraib
The price is €117
includes taxes & fees
4 Jun - 5 Jun
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (101 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is €264
includes taxes & fees
1 Jun - 2 Jun
Granville House
Front of property

Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is €164
includes taxes & fees
28 May - 29 May
Chambery Inn
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, (781 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is €170
includes taxes & fees
31 May - 1 Jun
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, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is €316
includes taxes & fees
28 May - 29 May
Devonfield Inn B&B
Exterior

The Whitlock

The Whitlock
2.0 star property
9.8 km from Chesterwood
8.6 out of 10, Excellent, (301 reviews)
"A beautiful old inn in the heart of a lovely old town."
United States
Linda
The price is €110
includes taxes & fees
27 May - 28 May
The Whitlock
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, (580 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is €72
includes taxes & fees
27 May - 28 May
Travelodge by Wyndham Great Barrington Berkshires
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, (1,005 reviews)
"Great location "
United States
Edith
The price is €108
includes taxes & fees
31 May - 1 Jun
Quality Inn Lee - Lenox South
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
10.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,005 reviews)
"enjoy your vacation"
United States
lev
The price is €165
includes taxes & fees
1 Jun - 2 Jun
The Cornell Inn, Lenox & The Berkshires
Standard Room, 2 Double Beds

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
4.7 km from Chesterwood
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
The price is €59
includes taxes & fees
27 May - 28 May
Pleasant Valley Motel West Stockbridge
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
13 km from Chesterwood
9.0 out of 10, Wonderful, (961 reviews)
"Great stay!"
United States
Aditya
The price is €110
includes taxes & fees
31 May - 1 Jun
Berkshires Untold
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area

East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.4 out of 10, Exceptional, (45 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
United States
Laura
The price is €140
includes taxes & fees
23 Jun - 24 Jun
East Rock Inn
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, (664 reviews)
"Good to stay. "
United States
Ibinabo
The price is €68
includes taxes & fees
2 Jun - 3 Jun
Econo Lodge Lee - Great Barrington
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
111 reviews
View
Exterior
The Red Lion Inn
3.5 star property
8.8
Excellent
1,002 reviews
View
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.2
Wonderful
902 reviews
View
Exterior
The Little Lion
3.0 star property
8.6
Excellent
562 reviews
View
Room, 2 Queen Beds, Non Smoking
Monument Mountain Motel
2.5 star property
9.0
Wonderful
857 reviews
View

Top Chesterwood Hotel Reviews

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10/10 Excellent
"2 empty nester couples visiting on a rainy weekend. House was exactly as advertised. Beautiful decor & comfortable furnishings. Communication with host excellent. Walkable to village of Stockbridge which was great. Host provided excellent recommendations on local attractions especially valuable on dreary weather. Highly recommend to adults, will return if in area."
Sue L. 3-night trip
Posted 22 hours ago
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Hotels near other Chesterwood attractions

Norman Rockwell Museum

4.7/5 (347 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

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 Lenox Arts Center while you're out sightseeing near Chesterwood.