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Check prices for these dates

This weekend
24 Jul - 26 Jul
Next weekend
31 Jul - 2 Aug

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Our top choices for Chesterwood hotels

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

1. 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, (113 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is ₹31,776
₹38,439 total
includes taxes & fees
5 Aug - 6 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior

2. 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, (793 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is ₹13,563
₹15,150 total
includes taxes & fees
16 Aug - 17 Aug
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

3. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
9.0 out of 10, Wonderful, (885 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens) Loved the place."
United States
Yekaterina
The price is ₹10,697
₹11,949 total
includes taxes & fees
27 Jul - 28 Jul
Monument Mountain Motel
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

4. East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.6 out of 10, Exceptional, (51 reviews)
"Virtual check in. I prefer real staff."
United States
Eleanor
The price is ₹14,981
₹16,733 total
includes taxes & fees
5 Aug - 6 Aug
East Rock Inn
Property amenity

5. 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, (941 reviews)
"Wonderful stay for families."
United States
Kimberly
The price is ₹16,544
₹20,361 total
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lobby

6. 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, (1,002 reviews)
"Great place"
United States
Michelle
The price is ₹13,007
₹14,529 total
includes taxes & fees
17 Aug - 18 Aug
Quality Inn Lee - Lenox South
Exterior

7. 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, (796 reviews)
"Extremely friendly and helpful staff upon arrival. Provide great insights on local restaurant opportunities, and included a five star breakfast. Highly recommend!"
United States
Lisa
The price is ₹18,733
₹20,925 total
includes taxes & fees
10 Aug - 11 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout curtains

8. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
16.9 km from Chesterwood
8.6 out of 10, Excellent, (1,003 reviews)
"Hotel was clean and staff helpful and courteous. Hotel is a little tired (showing it's age) but I would certainly not hesitate to book a future stay."
United States
Andrew
The price is ₹11,364
₹12,694 total
includes taxes & fees
5 Aug - 6 Aug
Best Western Plus Berkshire Hills Inn & Suites
Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

9. The Yankee Inn

The Yankee Inn
2.5 star property
14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,011 reviews)
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."
United States
Michael
The price is ₹18,189
₹20,318 total
includes taxes & fees
23 Jul - 24 Jul
The Yankee Inn
Exterior

10. The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (589 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is ₹12,126
₹13,545 total
includes taxes & fees
26 Jul - 27 Jul
The Little Lion
Lobby lounge

11. Berkshires Untold

Berkshires Untold
3.5 star property
13 km from Chesterwood
9.0 out of 10, Wonderful, (1,007 reviews)
"Nice place to stay."
United States
Debra
The price is ₹17,947
₹20,046 total
includes taxes & fees
5 Aug - 6 Aug
Berkshires Untold
Indoor pool

12. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
15.5 km from Chesterwood
9.4 out of 10, Exceptional, (139 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
The price is ₹16,361
₹18,275 total
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Front of property

13. Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (382 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
The price is ₹25,984
₹29,024 total
includes taxes & fees
23 Jul - 24 Jul
Chambery Inn
Property grounds

14. The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,006 reviews)
"Fantastic pool to top off the great location and fun historic hotel!"
United States
Antoinette G.
The price is ₹17,483
₹23,838 total
includes taxes & fees
3 Aug - 4 Aug
The Red Lion Inn
Lake view

15. Berkshire Lake Lodge

Berkshire Lake Lodge
16.2 km from Chesterwood
9.6 out of 10, Exceptional, (7 reviews)
"Everything was perfect!!"
United States
Grzegorz
The price is ₹18,490
₹20,653 total
includes taxes & fees
30 Jul - 31 Jul
Berkshire Lake Lodge
Lobby

16. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
10.3 km from Chesterwood
8.6 out of 10, Excellent, (1,000 reviews)
"Comfortable rooms within walking distance to Great Barrington."
United States
Lynn
The price is ₹12,708
₹14,195 total
includes taxes & fees
26 Jul - 27 Jul
Quality Inn Great Barrington
Lobby

17. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
15.9 km from Chesterwood
9.0 out of 10, Wonderful, (1,018 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is ₹14,136
₹17,939 total
includes taxes & fees
19 Aug - 20 Aug
Berkshire Mountain Lodge
Garden

18. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
5.8 km from Chesterwood
9.6 out of 10, Exceptional, (464 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ₹16,990
₹18,638 total
includes taxes & fees
27 Jul - 28 Jul
Shaker Mill Inn
Lobby

19. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.8 out of 10, Exceptional, (28 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is ₹22,809
₹25,478 total
includes taxes & fees
29 Jul - 30 Jul
Element by Marriott Lenox Berkshires
Front of property – evening/night

20. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
7.5 km from Chesterwood
10.0 out of 10, Exceptional, (139 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is ₹42,342
₹47,296 total
includes taxes & fees
19 Aug - 20 Aug
Devonfield Inn B&B
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
113 reviews
View
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8
Excellent
793 reviews
View
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
2.5 star property
9.0
Wonderful
885 reviews
View
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu
East Rock Inn
2.0 star property
9.6
Exceptional
51 reviews
View
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.2
Wonderful
941 reviews
View

Top Chesterwood Hotel Reviews

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

8/10 Good
"Rooms had not been updated since the seventies."
Deborah 1-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Hotels near other Chesterwood attractions

Norman Rockwell Museum

9.4/10 (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.

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