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Check prices for these dates

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

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Our top choices for Chesterwood hotels

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

1. 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, (853 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is ฿2,798
฿3,126 total
includes taxes & fees
3 Dec - 4 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

2. 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
9.2 out of 10, Wonderful, (1,005 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
The price is ฿3,686
฿4,117 total
includes taxes & fees
15 Nov - 16 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

3. 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, (820 reviews)
"Nice view and location for fall color."
United States
Md
The price is ฿5,416
฿6,050 total
includes taxes & fees
17 Nov - 18 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

4. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
8.7 km from Chesterwood
8.8 out of 10, Excellent, (938 reviews)
"Super clean and cozy and safe"
United States
Andrea
The price is ฿2,018
฿2,254 total
includes taxes & fees
3 Dec - 4 Dec
Monument Mountain Motel
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

5. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
9.1 km from Chesterwood
8.6 out of 10, Excellent, (1,002 reviews)
"Perfect for a travel stop-over."
United States
James
The price is ฿2,861
฿3,196 total
includes taxes & fees
2 Dec - 3 Dec
Quality Inn Lee - Lenox South
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

6. 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, (683 reviews)
"Great stay!"
United States
Vandhana
The price is ฿4,235
฿4,731 total
includes taxes & fees
3 Dec - 4 Dec
Courtyard by Marriott Lenox Berkshires
Two Adirondack chairs facing a river with a forested hill in the background.

7. The Yankee Inn

The Yankee Inn
2.5 star property
14.9 km from Chesterwood
9.2 out of 10, Wonderful, (1,010 reviews)
"The location was good for our trip."
United States
Basil
The price is ฿3,884
฿4,339 total
includes taxes & fees
20 Nov - 21 Nov
The Yankee Inn
A spacious hotel lobby with multiple seating areas, large windows, and a television.

8. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
14.7 km from Chesterwood
9.0 out of 10, Wonderful, (1,001 reviews)
"Breakfast was great"
United States
Thomas
The price is ฿3,697
฿4,130 total
includes taxes & fees
17 Nov - 18 Nov
Hampton Inn & Suites Berkshires-Lenox
A calm lake at dusk with a wooden dock and two chairs facing the water.

9. Berkshire Lake Lodge

Berkshire Lake Lodge
16.2 km from Chesterwood
9.8 out of 10, Exceptional, (27 reviews)
"excellent lakeside view"
United States
mike
The price is ฿3,678
฿4,108 total
includes taxes & fees
5 Nov - 6 Nov
Berkshire Lake Lodge
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

10. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
6.7 km from Chesterwood
9.2 out of 10, Wonderful, (1,002 reviews)
"Nice place to stay"
United States
Michael
The price is ฿3,732
฿4,830 total
includes taxes & fees
5 Nov - 6 Nov
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

11. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
15.5 km from Chesterwood
9.2 out of 10, Wonderful, (716 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is ฿4,001
฿4,469 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Lenox Pittsfield
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

12. Berkshires Untold

Berkshires Untold
3.5 star property
13 km from Chesterwood
9.0 out of 10, Wonderful, (1,063 reviews)
"A very good place to stay"
United States
Madhavi R
The price is ฿4,121
฿4,603 total
includes taxes & fees
29 Nov - 30 Nov
Berkshires Untold
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

13. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
12.5 km from Chesterwood
9.6 out of 10, Exceptional, (51 reviews)
"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"
United States
Francis
The price is ฿4,560
฿5,094 total
includes taxes & fees
9 Nov - 10 Nov
Element by Marriott Lenox Berkshires
Exterior

14. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
15.9 km from Chesterwood
9.0 out of 10, Wonderful, (1,253 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is ฿2,788
฿3,868 total
includes taxes & fees
11 Nov - 12 Nov
Berkshire Mountain Lodge
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

15. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
10.3 km from Chesterwood
8.6 out of 10, Excellent, (1,003 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is ฿2,555
฿2,854 total
includes taxes & fees
25 Nov - 26 Nov
Quality Inn Great Barrington
An indoor swimming pool with clear water, tiled floors, and a blue wall.

16. 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
9.2 out of 10, Wonderful, (254 reviews)
"This a much better Holiday Inn than the one at Saugerties that we went one day before."
United States
Yuguo
The price is ฿3,479
฿3,886 total
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

17. East Rock Inn

East Rock Inn
2.0 star property
10.1 km from Chesterwood
9.6 out of 10, Exceptional, (58 reviews)
"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."
United States
Sharon
The price is ฿4,457
฿4,978 total
includes taxes & fees
4 Dec - 5 Dec
East Rock Inn
A large house with a balcony and a grassy yard.

18. The Little Lion

The Little Lion
3.0 star property
5.1 km from Chesterwood
8.6 out of 10, Excellent, (637 reviews)
"A fine place for a quick overnight trip to the Berkshires."
United States
David
The price is ฿2,797
฿3,124 total
includes taxes & fees
9 Nov - 10 Nov
The Little Lion
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

19. The Red Lion Inn

The Red Lion Inn
3.5 star property
3.3 km from Chesterwood
8.8 out of 10, Excellent, (1,004 reviews)
"Enjoyed staying in the old hotel and loved the large porch with the bar to relax on."
United States
Mallory
The price is ฿5,321
฿7,621 total
includes taxes & fees
8 Nov - 9 Nov
The Red Lion Inn
A two-story building with a sign reading "Chambéry Inn".

20. Chambery Inn

Chambery Inn
3.0 star property
8.7 km from Chesterwood
9.6 out of 10, Exceptional, (390 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is ฿7,100
฿7,931 total
includes taxes & fees
3 Dec - 4 Dec
Chambery Inn
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
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8
Excellent
853 reviews
View
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.2
Wonderful
1,005 reviews
View
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
9.4
Exceptional
820 reviews
View
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
Monument Mountain Motel
2.5 star property
8.8
Excellent
938 reviews
View
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
Quality Inn Lee - Lenox South
2.5 star property
8.6
Excellent
1,002 reviews
View

Top Chesterwood Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Beautiful and historic ! Dinner was delicious!"
Teri 1-night trip
Posted 12 hours ago
The Red Lion Inn

Other attractions near Chesterwood

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 11 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 11 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.