10 Best Hotels & Accommodation Closest to Chesterwood in South Lee from NZ$121

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Our top choices for Chesterwood hotels

A lodge with a large building and a dock by a lake, surrounded by forest.

1. The Black Swan Lee - Lenox, an Ascend Collection Hotel

8.6 km from Chesterwood

Gustavo

includes taxes & fees

3 Dec - 4 Dec

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

2. Holiday Inn Express Hotel & Suites Great Barrington by IHG

8 km from Chesterwood

Cynthia

includes taxes & fees

7 Dec - 8 Dec

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

8.6 km from Chesterwood

Md

includes taxes & fees

15 Nov - 16 Nov

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

4. Monument Mountain Motel

8.7 km from Chesterwood

Martha

includes taxes & fees

10 Nov - 11 Nov

5. Quality Inn Lee - Lenox South

9.1 km from Chesterwood

Bernardo Jr

includes taxes & fees

2 Dec - 3 Dec

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

6. Courtyard by Marriott Lenox Berkshires

12.1 km from Chesterwood

Vandhana

includes taxes & fees

6 Dec - 7 Dec

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

7. The Yankee Inn

14.9 km from Chesterwood

Stephanie

includes taxes & fees

20 Nov - 21 Nov

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

8. Hampton Inn & Suites Berkshires-Lenox

14.7 km from Chesterwood

Thomas

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

9. Element by Marriott Lenox Berkshires

12.5 km from Chesterwood

Francis

includes taxes & fees

29 Nov - 30 Nov

A grassy area with a lake, trees, and red chairs arranged around a fire pit.

10. Berkshire Lake Lodge

16.2 km from Chesterwood

mike

includes taxes & fees

10 Nov - 11 Nov

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

11. Berkshires Untold

13 km from Chesterwood

Brian

includes taxes & fees

17 Nov - 18 Nov

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

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

6.7 km from Chesterwood

Michael

includes taxes & fees

10 Nov - 11 Nov

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

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

15.5 km from Chesterwood

Ruth

includes taxes & fees

15 Nov - 16 Nov

14. Berkshire Mountain Lodge

15.9 km from Chesterwood

Susan J

includes taxes & fees

6 Dec - 7 Dec

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

10.3 km from Chesterwood

Lynne

includes taxes & fees

29 Nov - 30 Nov

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

16. East Rock Inn

10.1 km from Chesterwood

Sharon

includes taxes & fees

10 Dec - 11 Dec

A hotel patio with outdoor seating and a fire pit.

17. Hilton Garden Inn Lenox Pittsfield

15.5 km from Chesterwood

James

includes taxes & fees

22 Nov - 23 Nov

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

18. The Cornell Inn, Lenox & The Berkshires

10.7 km from Chesterwood

judith

includes taxes & fees

10 Nov - 11 Nov

A crowded outdoor event with tents and people gathered in a grassy area.

19. Chambery Inn

8.7 km from Chesterwood

Alexandra

includes taxes & fees

22 Nov - 23 Nov

A red building with a sign reading "Shaker Mill Inn."

20. Shaker Mill Inn

5.8 km from Chesterwood

Mahadeva

includes taxes & fees

12 Nov - 13 Nov

View all properties

Compare popular hotels close to Chesterwood

Property	Property class	Guest rating
The Black Swan Lee - Lenox, an Ascend Collection Hotel	3.0 star property	9.2 Wonderful 1,001 reviews	View
Holiday Inn Express Hotel & Suites Great Barrington by IHG	2.5 star property	8.8 Excellent 856 reviews	View
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires	3.0 star property	9.4 Exceptional 822 reviews	View
Monument Mountain Motel	2.5 star property	9.0 Wonderful 942 reviews	View
Quality Inn Lee - Lenox South	2.5 star property	8.6 Excellent 1,004 reviews	View

Top Chesterwood Hotel Reviews

The Red Lion Inn

10/10 Excellent

"The Red lion Inn is a unique historical stay. The hotel is charming with so many historical items to look at every turn. There are plenty of cute shops and great hiking trails right down the road."

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

10/10 Excellent

"This was such a delightful find! We came here on a fall foliage trip to celebrate my sister-in-law's 50th birthday. The house is super charming and magically situated at the end of a street right by a river and trails. We were dying that we could simply walk out the front door and be in nature. The house is also located so close to so many lovely things to do. We spent time shopping in Stockbridge and nearby Lenox. We walked into town to catch our shuttle for the Naumkeag Pumpkin Show--not to be missed! Just down the road we went apple picking at Windy Hill Farm and on a hike up Monument Mountain. Our host was so easy to communicate with and we felt very welcome. I'm so glad she's willing to share her little piece of heaven with others."

A Grand property in Historic Stockbridge

10/10 Excellent

"My husband and his 5 sibs and their partners and I just spent 3 glorious days at the Taggart House. The house is spacious but cozy with the help of two strategically placed electric fireplaces AND new thermostats. There are many spaces to gather (or separate!), including a back patio we were able to utilize b/c the weather was so gorgeous. From the patio we had great views of the vast lawn leading down to the river. Beautiful! All of us appreciated the number of bedrooms and en suite baths given our age range—61-71. And every one of us appreciated the history of the house and the efforts to keep furnishings historically and stylistically appropriate. The house is comfortably appointed, not too precious, fun to move through once you learn the lay of the land, and in a perfect location on the edge of downtown Stockbridge. We’re already planning a return trip."

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

10/10 Excellent

"We found the Taggart House to be so convenient to the town of Stockbridge - it was a pleasure to be able to walk to the park with our kids, pick up a delicious local coffee or simply do some shopping in the interesting local shops. Even though it was close and on main street, it is set on the back part of the property overlooking the Housitonic River which was lovely, relaxing, very quiet and peaceful. We enjoyed the spaciousness of the home and the large kitchen, the rain showers in all of the bathrooms, two oversized soaking tubs and it was a real treat to have a laundry room on both floors! A big Thank You! to the owners for sharing their home for our family vacation!"

Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay

10/10 Excellent

"The home was exactly as expected - So beautiful and accommodating. Communication with the host was excellent. We had a wonderful time in Woodland Zen. Can’t wait to return!"

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.

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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.

Top Hotels Near Chesterwood in South Lee from NZ$121

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Our top choices for Chesterwood hotels

1. The Black Swan Lee - Lenox, an Ascend Collection Hotel

2. Holiday Inn Express Hotel & Suites Great Barrington by IHG

3. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

4. Monument Mountain Motel

5. Quality Inn Lee - Lenox South

6. Courtyard by Marriott Lenox Berkshires

7. The Yankee Inn

8. Hampton Inn & Suites Berkshires-Lenox

9. Element by Marriott Lenox Berkshires

10. Berkshire Lake Lodge

11. Berkshires Untold

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

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

14. Berkshire Mountain Lodge

15. Quality Inn Great Barrington

16. East Rock Inn

17. Hilton Garden Inn Lenox Pittsfield

18. The Cornell Inn, Lenox & The Berkshires

19. Chambery Inn

20. Shaker Mill Inn

Compare popular hotels close to Chesterwood

Top Chesterwood Hotel Reviews

The Red Lion Inn

Other attractions near Chesterwood

Norman Rockwell Museum

Frequently asked questions