The Best Hotels Closest to Chesterwood in South Lee for 2026

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Our top choices for Chesterwood hotels

A two-story house with a brick entrance and a white facade.

1. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

0.6 km from Chesterwood

Philippe

SAR 1,734 total

includes taxes & fees

28 Nov - 29 Nov

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

2. Monument Mountain Motel

8.7 km from Chesterwood

Martha

SAR 251 total

includes taxes & fees

15 Nov - 16 Nov

3. Quality Inn Lee - Lenox South

9.1 km from Chesterwood

Bernardo Jr

SAR 358 total

includes taxes & fees

6 Dec - 7 Dec

A calm lake at dusk with a wooden dock and two chairs facing the water.

4. Berkshire Lake Lodge

16.2 km from Chesterwood

mike

SAR 475 total

includes taxes & fees

15 Nov - 16 Nov

Two Adirondack chairs facing a river with a forested hill in the background.

5. The Yankee Inn

14.9 km from Chesterwood

Stephanie

SAR 445 total

includes taxes & fees

13 Dec - 14 Dec

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

6. Berkshires Untold

13 km from Chesterwood

Juan

SAR 441 total

includes taxes & fees

19 Nov - 20 Nov

A two-story building with a sign reading "Chambéry Inn".

7. Chambery Inn

8.7 km from Chesterwood

Alexandra

SAR 795 total

includes taxes & fees

15 Nov - 16 Nov

A hotel room with two beds, a desk with a chair, a small table, and a TV.

8. Element by Marriott Lenox Berkshires

12.5 km from Chesterwood

Francis

SAR 566 total

includes taxes & fees

29 Nov - 30 Nov

A spacious hotel lobby with multiple seating areas, large windows, and a television.

9. Hampton Inn & Suites Berkshires-Lenox

14.7 km from Chesterwood

Thomas

SAR 460 total

includes taxes & fees

22 Nov - 23 Nov

10. Berkshire Mountain Lodge

15.9 km from Chesterwood

Susan J

SAR 406 total

includes taxes & fees

13 Dec - 14 Dec

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

11. Courtyard by Marriott Lenox Berkshires

12.1 km from Chesterwood

Vandhana

SAR 477 total

includes taxes & fees

13 Dec - 14 Dec

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

12. Hilton Garden Inn Lenox Pittsfield

15.5 km from Chesterwood

James

SAR 498 total

includes taxes & fees

15 Nov - 16 Nov

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

13. Quality Inn Great Barrington

10.3 km from Chesterwood

David

SAR 317 total

includes taxes & fees

3 Dec - 4 Dec

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

14. East Rock Inn

10.1 km from Chesterwood

Sharon

SAR 510 total

includes taxes & fees

13 Dec - 14 Dec

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

15. Brook Farm Inn

9.1 km from Chesterwood

Carrie

SAR 722 total

includes taxes & fees

13 Nov - 14 Nov

An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

15.5 km from Chesterwood

Ruth

SAR 432 total

includes taxes & fees

13 Dec - 14 Dec

A swimming pool with a fenced area, lounge chairs, and a warning sign.

17. Sunset Inn

9.1 km from Chesterwood

Lauren

SAR 323 total

includes taxes & fees

25 Nov - 26 Nov

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

18. Howard Johnson by Wyndham Lenox

14.9 km from Chesterwood

Aleksandr

SAR 331 total

includes taxes & fees

22 Nov - 23 Nov

19. The Inn at Stockbridge

5.2 km from Chesterwood

Kimberly

SAR 1,015 total

includes taxes & fees

15 Nov - 16 Nov

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

20. Best Western Plus Berkshire Hills Inn & Suites

16.9 km from Chesterwood

James

SAR 392 total

includes taxes & fees

3 Dec - 4 Dec

View all properties

Other attractions near Chesterwood

Norman Rockwell Museum

9.4/10 (347 reviews)

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.

See properties

Top Chesterwood Hotel Reviews

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

10/10 Excellent

Charles

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

The Inn at Stockbridge

Stockbridge

10/10 Excellent

Kevin

Brook Farm Inn

Lenox

10/10 Excellent

roberta

Chambery Inn

Lee

10/10 Excellent

Elaine

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

Great Barrington

10/10 Excellent

We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!

Anonymous traveler

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

A snow-covered outdoor area with a patio, seating, and a covered dining area.

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lawrence

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

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

South Lee

10/10 Excellent

I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...

David

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

Lee

10/10 Excellent

Sheila

Wilder House Berkshires

Sheffield

10/10 Excellent

Liliana

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

Little Cat Lodge

Copake Falls

10/10 Excellent

Elisabeth

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

The Red Lion Inn

Stockbridge

10/10 Excellent

Michael

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, check out the 11 hotels and other accommodations you'll find within a mile.

What's the best hotel 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 traveler 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 are there close to Chesterwood?

Expedia has 11 hotels and other accommodations within a mile from Chesterwood.

If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?

Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to review the best options available near Chesterwood.

Where can I learn more about changing or cancelling my trip in the area near Chesterwood?

For more information about picking new dates or cancelling your stay near Chesterwood, head over to our customer service page.

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.

Find hotels near Chesterwood, South Lee from SAR 224

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Our top choices for Chesterwood hotels

1. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

2. Monument Mountain Motel

3. Quality Inn Lee - Lenox South

4. Berkshire Lake Lodge

5. The Yankee Inn

6. Berkshires Untold

7. Chambery Inn

8. Element by Marriott Lenox Berkshires

9. Hampton Inn & Suites Berkshires-Lenox

10. Berkshire Mountain Lodge

11. Courtyard by Marriott Lenox Berkshires

12. Hilton Garden Inn Lenox Pittsfield

13. Quality Inn Great Barrington

14. East Rock Inn

15. Brook Farm Inn

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

17. Sunset Inn

18. Howard Johnson by Wyndham Lenox

19. The Inn at Stockbridge

20. Best Western Plus Berkshire Hills Inn & Suites

Other attractions near Chesterwood

Norman Rockwell Museum

Top Chesterwood Hotel Reviews

Devonfield Inn B&B

10/10 Excellent

Frequently Asked Questions

What's the area like around Chesterwood?

What's the best hotel to stay close to Chesterwood?

How many hotels are there close to Chesterwood?

If I need to cancel the hotel reservation for my stay near Chesterwood, will I receive a refund?

Where can I learn more about changing or cancelling my trip in the area near Chesterwood?

What can I see and do near Chesterwood?