The Best Hotels Closest to Chesterwood in South Lee for 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Chesterwood hotels

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

A motel with a parking lot and several cars parked.

A hotel room with a wooden dresser, a television, a microwave, and a mirror.

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

1. Monument Mountain Motel

8.7 km from Chesterwood

Victor

￥10,758

￥12,016 total

includes taxes & fees

Oct 25 - Oct 26

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

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

8.6 km from Chesterwood

Bruce

￥26,604

￥29,717 total

includes taxes & fees

Oct 1 - Oct 2

A large, two-story house with a well-maintained lawn and a fence.

A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.

A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.

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

3. Devonfield Inn B&B

7.5 km from Chesterwood

Sebastien

￥64,328

￥71,854 total

includes taxes & fees

Oct 25 - Oct 26

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

4. Quality Inn Lee - Lenox South

9.1 km from Chesterwood

Wendy

￥17,246

￥19,263 total

includes taxes & fees

Oct 19 - Oct 20

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

A room with two beds, a round mirror, a red box, and a hanging light fixture.

A lakeside dock with chairs and a table, surrounded by greenery and a clear sky.

A small, modern room with a desk, chair, and a flat-screen TV mounted on the wall.

5. Berkshire Lake Lodge

16.2 km from Chesterwood

mike

￥21,017

￥23,476 total

includes taxes & fees

Sep 28 - Sep 29

A modern hotel lobby with seating areas, tables, and a reception desk.

A breakfast area with a counter, coffee machine, and a display of pastries.

A hotel room with two beds, a desk, a TV, and a window with curtains.

A coffee station with two coffee machines and a variety of coffee pods and cups.

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

8 km from Chesterwood

Maria Dulce

￥18,716

￥20,905 total

includes taxes & fees

Oct 19 - Oct 20

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A spacious lobby with a fireplace, seating area, and a bar.

A garden with wooden Adirondack chairs and a stone pathway.

7. Berkshire Mountain Lodge

15.9 km from Chesterwood

Jay

￥12,519

￥17,497 total

includes taxes & fees

Oct 1 - Oct 2

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

A cozy library with bookshelves, a fireplace, and comfortable seating.

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

8. Berkshires Untold

13 km from Chesterwood

Drue

￥22,009

￥24,584 total

includes taxes & fees

Sep 28 - Sep 29

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

A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

9. East Rock Inn

10.1 km from Chesterwood

ERIK

￥22,486

￥25,117 total

includes taxes & fees

Oct 12 - Oct 13

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

An outdoor seating area with Adirondack chairs and a fire feature.

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

10. Element by Marriott Lenox Berkshires

12.5 km from Chesterwood

Kirsty

￥26,580

￥29,689 total

includes taxes & fees

Oct 18 - Oct 19

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

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

11. Little Cat Lodge

16.3 km from Chesterwood

Kees

￥28,169

￥31,550 total

includes taxes & fees

Sep 28 - Sep 29

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

A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

12. Best Western Plus Berkshire Hills Inn & Suites

16.9 km from Chesterwood

Joe

￥16,637

￥18,583 total

includes taxes & fees

Oct 18 - Oct 19

A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.

A covered corridor with a metal railing, white walls, and a view of a street with parked cars.

A hotel room with two beds, a chair, and a bedside table with a phone.

A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.

13. Sunset Inn

9.1 km from Chesterwood

Lauren

￥11,911

￥13,304 total

includes taxes & fees

Oct 7 - Oct 8

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

A Quality Inn sign, a brick building, and a parking lot with cars.

A hotel room with a bathroom, a bed, a desk, and a nightstand.

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

14. Quality Inn Great Barrington

10.3 km from Chesterwood

Joan

￥15,909

￥17,771 total

includes taxes & fees

Oct 18 - Oct 19

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

A spacious living room with a large sofa, a coffee table, and a fireplace.

A hotel patio with outdoor seating and a fire pit.

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

15. Hilton Garden Inn Lenox Pittsfield

15.5 km from Chesterwood

James

￥23,007

￥25,700 total

includes taxes & fees

Oct 25 - Oct 26

A large house with a balcony and a grassy yard.

A two-story building with a gabled roof and a chimney.

A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.

A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

16. The Little Lion

5.1 km from Chesterwood

Mary

￥16,278

￥18,183 total

includes taxes & fees

Oct 18 - Oct 19

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

A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

A cozy room with a bed, a sofa, a small table, and a desk. There are two lamps on the bed and a window with curtains.

A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

17. Shaker Mill Inn

5.8 km from Chesterwood

Mervin

￥28,153

￥30,884 total

includes taxes & fees

Oct 1 - Oct 2

A stone fountain surrounded by trees in a park setting.

A living room with a fireplace, leather sofas, and a dog.

18. The Inn at Stockbridge

5.2 km from Chesterwood

Jodi

￥68,885

￥80,791 total

includes taxes & fees

Sep 28 - Sep 29

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

A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.

A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.

A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.

19. Brook Farm Inn

9.1 km from Chesterwood

Carrie

￥26,222

￥30,547 total

includes taxes & fees

Sep 28 - Sep 29

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

A compact living space with a kitchenette, a dining area, and a sofa.

A hotel room with two beds, a nightstand with a lamp, and a window with curtains.

A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

20. The Central Downtown Inn & Suites

19.6 km from Chesterwood

Rena

￥15,571

￥17,392 total

includes taxes & fees

Sep 28 - Sep 29

View all properties

Top Chesterwood Hotel Reviews

The Red Lion Inn

10/10 Excellent

"If you want a perfect New England experience, this is the place. The hotel is amazing, it’s older so don’t think you’re going to walk into a modern place, but don’t let that deter you, the vibe is great! Will definitely stay here again."

Secluded Family Home in Serene Stockbridge Woods

10/10 Excellent

"Overall, lovely tidy house for family stays. Host is very accessible and friendly. Great location in quiet woods close to neighboring towns with lots of amenities. Best for casual folks who are comfortable dealing with forest critters should they come about. We didn't encounter any, but it would have been ok if we had. Only suggestion would be to have more hooks upstairs for hanging up damp towels and brighter lighting in the bedrooms. Loved the stars on the ceilings!"

A Grand property in Historic Stockbridge

10/10 Excellent

"The Taggart House exceeded our expectations. We were a group 5 women, grade school BFFs, celebrating a milestone birthday….. loved having our own bedrooms and bathrooms, more so because they were totally renovated. The sun porch was our favorite spot for everything - cozy, comfy and gorgeous. Our hosts happened to be nearby over the weekend and even set up our evening fire pit to ensure the required s’more-fest was a success. Highly recommend!"

Hearth House | Prime Location!

10/10 Excellent

"Comfortable home in a great neighborhood."

Tranquil 3 BR Stockbridge House w/ Private Deck!

10/10 Excellent

"Another wonderful weekend at the Redway House … our 4th stay. And … we’ll be back in October! Our favorite things are hanging out on the deck, the comfy beds and being close to everything while being in a very quiet location! An awesome getaway!"

8 Mi to Tanglewood & Butternut Ski: Spacious Home!

10/10 Excellent

"We had an amazing stay and the area the house is in is perfect to visit all that the Berkshires has to offer! Loved our stay so much! Thank you!"

Vacation in a Berkshire Farmhouse

10/10 Excellent

"We had a wonderful stay at the farmhouse. I have been coming to the Berkshires for many years, and found this home to be the most perfect for our needs! The place was immaculate, comfortable beds, plenty of towels and linens. It was a great place for reunion of friends and family, a great place to gather and enjoy all that the Berkshires have to offer. I loved all of the spaces to hang out, the delightful screened porch in the mornings, the dining room was such a nice place to share meals, and the living room to hang out in the evenings. The property itself is so very beautiful, and a touch of whimsy with all of Elaine's garden sculptures in front of her studio. I forgot to mention that the location was also excellent I definitely will return! Thanks for everything Elaine!!"

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

10/10 Excellent

"We love the beautiful Taggart River House! This was our second stay--eight of us really enjoyed our return visit to Stockbridge, Tanglewood and the Berkshires. The location is superb--walking distance to downtown Stockbridge can never be overrated. Short drives to everything else make this property ideal. Super responsive and helpful hosts! Very clean, well-appointed rooms and facilities, more than ample parking and easy-to-follow house rules and recommendations. Pictures are accurate. You will love it!"

Experienced Hosts. Quiet, Romantic, Spacious Apartment, Pet Friendly.

8/10 Good

"ok"

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

Berkshire Botanical Garden

9.4/10 (14 reviews)

Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.

See properties

Mission House

9.6/10 (5 reviews)

You can spend time exploring the galleries in Mission House in Stockbridge. Wander the lakeside in this quaint area.

See properties

Naumkeag Museum

9.4/10 (10 reviews)

You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside.

See properties

National Shrine of the Divine Mercy

9.0/10 (83 reviews)

Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.

See properties

Schantz Galleries

7.2/10 (5 reviews)

You can spend an afternoon exploring the galleries in Schantz Galleries during your trip to Stockbridge. Wander the lakeside in this quaint area.

See properties

Art et Industrie

8.0/10 (5 reviews)

You can spend an afternoon exploring the galleries in Art et Industrie in Great Barrington. Amble around this quaint area's gardens, or seek out the hiking trails.

See properties

Berkshire Theatre Festival

8.8/10 (3 reviews)

You can get tickets for a performance at Berkshire Theatre Festival on 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, 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 ￥12,016

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Chesterwood hotels

1. Monument Mountain Motel

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

3. Devonfield Inn B&B

4. Quality Inn Lee - Lenox South

5. Berkshire Lake Lodge

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

7. Berkshire Mountain Lodge

8. Berkshires Untold

9. East Rock Inn

10. Element by Marriott Lenox Berkshires

11. Little Cat Lodge

12. Best Western Plus Berkshire Hills Inn & Suites

13. Sunset Inn

14. Quality Inn Great Barrington

15. Hilton Garden Inn Lenox Pittsfield

16. The Little Lion

17. Shaker Mill Inn

18. The Inn at Stockbridge

19. Brook Farm Inn

20. The Central Downtown Inn & Suites

Top Chesterwood Hotel Reviews

The Red Lion Inn

Secluded Family Home in Serene Stockbridge Woods

A Grand property in Historic Stockbridge

Hearth House | Prime Location!

Tranquil 3 BR Stockbridge House w/ Private Deck!

8 Mi to Tanglewood & Butternut Ski: Spacious Home!

Vacation in a Berkshire Farmhouse

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

Experienced Hosts. Quiet, Romantic, Spacious Apartment, Pet Friendly.

Other attractions near Chesterwood

Norman Rockwell Museum

Berkshire Botanical Garden

Mission House

Naumkeag Museum

National Shrine of the Divine Mercy

Schantz Galleries

Art et Industrie

Berkshire Theatre Festival

Frequently asked questions