The Best Hotels Closest to Stockbridge Bowl in Stockbridge for 2026

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Our top choices for Stockbridge Bowl hotels

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

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.

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.

1. Brook Farm Inn

3.1 km from Stockbridge Bowl

Carrie

₩260,352

₩301,524 total

includes taxes & fees

Nov 2 - Nov 3

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

2. The Yankee Inn

8.7 km from Stockbridge Bowl

William

₩141,881

₩158,482 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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.

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

13.7 km from Stockbridge Bowl

Maria Dulce

₩136,527

₩152,495 total

includes taxes & fees

Oct 25 - Oct 26

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

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

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

4. Quality Inn Lee - Lenox South

7.3 km from Stockbridge Bowl

Christine

₩124,012

₩138,522 total

includes taxes & fees

Nov 5 - Nov 6

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A dining area with large windows, wooden furniture, and a view of a lake.

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

A lakeside dock with kayaks and a covered boat ramp.

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

5.1 km from Stockbridge Bowl

Bob

₩154,731

₩172,834 total

includes taxes & fees

Nov 1 - Nov 2

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

A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

6. Hampton Inn & Suites Berkshires-Lenox

8.5 km from Stockbridge Bowl

Thomas

₩153,660

₩171,638 total

includes taxes & fees

Nov 4 - Nov 5

A building entrance with a large planter with purple flowers and a small tree.

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

7. Hotel On North

14.1 km from Stockbridge Bowl

Lawrence

₩149,578

₩167,078 total

includes taxes & fees

Nov 1 - Nov 2

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

A garden with wooden Adirondack chairs and a stone pathway.

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

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

8. Berkshire Mountain Lodge

9.7 km from Stockbridge Bowl

marilyn

₩114,740

₩158,066 total

includes taxes & fees

Oct 20 - Oct 21

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

A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

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

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

9. Element by Marriott Lenox Berkshires

6.3 km from Stockbridge Bowl

Kirsty

₩202,114

₩225,761 total

includes taxes & fees

Nov 1 - Nov 2

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

A hotel patio with outdoor seating and a fire pit.

A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

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

10. Hilton Garden Inn Lenox Pittsfield

9.3 km from Stockbridge Bowl

James

₩171,167

₩191,191 total

includes taxes & fees

Nov 1 - Nov 2

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

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

11. Monument Mountain Motel

14.5 km from Stockbridge Bowl

Andrea

₩80,109

₩89,479 total

includes taxes & fees

Nov 5 - Nov 6

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 corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

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

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

14.4 km from Stockbridge Bowl

Bruce

₩192,276

₩214,772 total

includes taxes & fees

Nov 2 - Nov 3

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

A modern cafe with a counter, seating area, and large windows.

A snack bar with shelves of snacks and a refrigerated display.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

9.2 km from Stockbridge Bowl

Sheldon

₩137,866

₩153,997 total

includes taxes & fees

Nov 4 - Nov 5

A building with a porch and multiple windows, surrounded by purple flowers.

A living room with a sofa, armchair, coffee table, and a patterned rug.

A café with a display case, a frozen food section, and a marketplace sign.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

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

7.8 km from Stockbridge Bowl

Jared

₩156,604

₩201,095 total

includes taxes & fees

Oct 12 - Oct 13

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.

15. Best Western Plus Berkshire Hills Inn & Suites

11 km from Stockbridge Bowl

Joe

₩125,123

₩139,762 total

includes taxes & fees

Nov 1 - Nov 2

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 two-story house with a covered porch, a driveway, and a lawn with outdoor seating.

16. Berkshire Lake Lodge

14.3 km from Stockbridge Bowl

mike

₩189,732

₩211,931 total

includes taxes & fees

Oct 8 - Oct 9

A large house with a balcony and a grassy yard.

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.

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

17. The Little Lion

10.6 km from Stockbridge Bowl

Lidia

₩138,535

₩154,743 total

includes taxes & fees

Oct 18 - Oct 19

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

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

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

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

18. Berkshires Untold

6.8 km from Stockbridge Bowl

Madhavi R

₩176,216

₩196,833 total

includes taxes & fees

Nov 1 - Nov 2

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

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

19. Howard Johnson by Wyndham Lenox

8.7 km from Stockbridge Bowl

Mark

₩105,742

₩118,114 total

includes taxes & fees

Oct 12 - Oct 13

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

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

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

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

20. Quality Inn Great Barrington

16.3 km from Stockbridge Bowl

Joan

₩102,397

₩114,377 total

includes taxes & fees

Nov 1 - Nov 2

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Compare popular hotels close to Stockbridge Bowl

Property	Property class	Guest rating
Brook Farm Inn	9.4 Exceptional 175 reviews	View
The Yankee Inn	9.2 Wonderful 1,007 reviews	View
Holiday Inn Express Hotel & Suites Great Barrington by IHG	8.8 Excellent 835 reviews	View
Quality Inn Lee - Lenox South	8.6 Excellent 1,006 reviews	View
The Black Swan Lee - Lenox, an Ascend Collection Hotel	9.2 Wonderful 1,000 reviews	View

Top Stockbridge Bowl Hotel Reviews

The Red Lion Inn

8/10 Good

"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Delightful and charming! When you go to an inn that is over 200 years old you don’t know what to expect and everything was a wonderful surprise. Super clean, stylish, and staff that was warm and friendly. We had what we believe was the smallest room in the Inn, not much over 100 ft.², and it was perfect for a one night stay. The breakfast options were a real treat!"

Hideaway Inn Lenox

8/10 Good

"I had to followup with the check in procedure as I never received an email link that worked and the message was not texted to me because my telephone number was incorrect. Parking was tight and coming back after dinner the only spot available was at one of the electric car charging areas. We also unexpectedly found a personal item under one of the beds that must have been left behind by previous guests. The inn itself was quiet, on a beautiful lot/setting and interior uniquely decorated with pretty common sitting areas we enjoyed. While a little less expensive than other inns, for the cost, it's unfortunate the inn operates remotely/independently, as it would have been nice to enjoy a continental breakfast. However, overall, we enjoyed our stay and would consider returning again!"

Brook Farm Inn

8/10 Good

"We were greeted by one of the staff with the aroma of fresh baked cookies, lovely! She showed us around the inn then to our room — “The Berkshire Room” which is in the main inn on the 2nd floor. The room was charming and comfortable with period details, a comfortable bed, small sitting area, tall ceiling, a small wall mounted TV, and a fireplace (nonfunctional) with mantle. The bathroom is nice, but the shower stall is tight. The inn is conveniently located just down the hill from Lenox village. There was a wedding nearby that pumped out music, which was a little annoying, but it stopped at 9:30"

Shaker Mill Inn

10/10 Excellent

"Everything was just perfect, except for the housekeeper didn’t make the bed and empty the trash"

Pleasant Valley Motel West Stockbridge

8/10 Good

"The room was fairly clean, but the wallpaper is peeling away from the wall. The towel hanging on the towel rod had dark gray streaks like it had already been used."

Eastgate Inn B&B

10/10 Excellent

"Very welcoming host."

33 Main

8/10 Good

"This was our second stay at 33 Main. Wonderfully maintain, homey environment, with friendly, welcoming and helpful staff. Welcoming cookies, and beautiful water bottle. They even remembered that we asked for the beach and gave us excellent recommendation. Convenient parking in the back. My only suggestion for improvement is breakfast - last year it was much better."

Hampton Terrace Inn

10/10 Excellent

"Hot tub in the cottage was wonderful. The provided guide was very comprehensive and we appreciated all the amenities available in the main and carriage house. "

Other attractions near Stockbridge Bowl

A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

Tanglewood Music Center

9.6/10 (457 reviews)

You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.

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A large white mansion surrounded by dense green trees and a clear blue sky with clouds.

The Mount

9.4/10 (174 reviews)

You can spend an afternoon studying the exhibits at The Mount during your trip to Lenox. While you're in the area, stroll along the lakeside.

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Frelinghuysen Morris House and Studio

8.2/10 (10 reviews)

You can spend time exploring the galleries in Frelinghuysen Morris House and Studio during your trip to Stockbridge. Wander the lakeside in this family-friendly area.

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Shakespeare and Company

9.2/10 (76 reviews)

You can get tickets for a performance at Shakespeare and Company during your stay in Lenox. While you're in the area, stroll along the lakeside.

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Berkshire Performing Arts Center

Enjoy an outing to Berkshire Performing Arts Center during your stay in Lenox. Wander around the gardens or experience the area's museums.

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Lenox Library

9.0/10 (45 reviews)

Lenox Library is just one of the places to see in Lenox, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's gardens or attend a sporting event.

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Ventfort Hall Mansion and Gilded Age Museum

9.2/10 (65 reviews)

You can spend an afternoon exploring the galleries in Ventfort Hall Mansion and Gilded Age Museum during your travels in Lenox. Wander the lakeside in this family-friendly area.

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Charles H. Baldwin & Sons

Enjoy an outing to Charles H. Baldwin & Sons during your stay in West Stockbridge. Wander the lakeside in this quaint area.

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Frequently asked questions

What's the area like around Stockbridge Bowl?

Stockbridge Bowl is located in Stockbridge. Travelers like this historic area for its bars. If you're looking for a convenient place to stay, check out the 20 hotels and other accommodations you'll find within a mile.

Where is the best place to stay close to Stockbridge Bowl?

The Whitlock is one of the top choices for your stay based on our traveler data, and this hotel offers free parking and free WiFi. It's located 2.4 mi (3.8 km) from Stockbridge Bowl. Other good choices within 5 miles include Eastgate Inn B&B and The Black Swan Lee - Lenox, an Ascend Collection Hotel.

How many hotels should I expect to find close to Stockbridge Bowl?

Expedia has 20 hotels and other accommodations within a mile from Stockbridge Bowl.

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

Yes, most hotel bookings are fully refundable if you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you have a non-refundable reservation, you might still have the option to cancel and receive a refund within a 24-hour period of your booking. Plug in your dates, click on "Search", then filter by "fully refundable" to view the best options available near Stockbridge Bowl.

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

For more information about updating your stay near Stockbridge Bowl or cancelling it, click here.

What can I see and do near Stockbridge Bowl?

You'll want to browse the collections at Ventfort Hall Mansion and Gilded Age Museum, Norman Rockwell Museum, and Berkshire Scenic Railway Museum. The Mount, Lenox Library, and Naumkeag Museum are landmarks that you won't want to miss. You can check out the local talent at Tanglewood Music Center, Shakespeare and Company, and Berkshire Theatre Festival.

Find hotels near Stockbridge Bowl, Stockbridge from ₩89,479

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Treat yourself

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Our top choices for Stockbridge Bowl hotels

1. Brook Farm Inn

2. The Yankee Inn

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

4. Quality Inn Lee - Lenox South

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

6. Hampton Inn & Suites Berkshires-Lenox

7. Hotel On North

8. Berkshire Mountain Lodge

9. Element by Marriott Lenox Berkshires

10. Hilton Garden Inn Lenox Pittsfield

11. Monument Mountain Motel

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

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

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

15. Best Western Plus Berkshire Hills Inn & Suites

16. Berkshire Lake Lodge

17. The Little Lion

18. Berkshires Untold

19. Howard Johnson by Wyndham Lenox

20. Quality Inn Great Barrington

Compare popular hotels close to Stockbridge Bowl

Top Stockbridge Bowl Hotel Reviews

The Red Lion Inn

The Cornell Inn, Lenox & The Berkshires

Hideaway Inn Lenox

Brook Farm Inn

Shaker Mill Inn

Pleasant Valley Motel West Stockbridge

Eastgate Inn B&B

33 Main

Hampton Terrace Inn

Other attractions near Stockbridge Bowl

Tanglewood Music Center

The Mount

Frelinghuysen Morris House and Studio

Shakespeare and Company

Berkshire Performing Arts Center

Lenox Library

Ventfort Hall Mansion and Gilded Age Museum

Charles H. Baldwin & Sons

Frequently asked questions