A large white house with multiple chimneys, surrounded by lush greenery and trees.

B&B in Lenox

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B&B in Lenox

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

A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

A modern living room with a fireplace, comfortable seating, and a large window with curtains.

1. The Cornell Inn, Lenox & The Berkshires

Lenox

$156

$179 total

includes taxes & fees

Oct 27 - Oct 28

A garden with a white gazebo, a brick pathway, and various plants and flowers.

A breakfast buffet with various dishes and beverages.

A spacious living room with a grand piano, a red armchair, and a chandelier.

A house surrounded by trees with autumn foliage.

2. Whistler's Inn Bed & Breakfast

Lenox

$188

$210 total

includes taxes & fees

Oct 19 - Oct 20

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

A cozy room with a fireplace, a sofa, a table with a bottle and glasses, and a patterned pillow.

A hotel room with a TV displaying 'World of Dance', a fireplace, a bed, and a seating area with a remote control.

A hotel room with a large bed, a TV mounted above a fireplace, a desk, and a seating area with chairs.

3. Chambery Inn

Lee

$300

$335 total

includes taxes & fees

Oct 19 - Oct 20

A stone fountain surrounded by trees in a park setting.

A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.

4. The Inn at Stockbridge

Stockbridge

$365

$428 total

includes taxes & fees

Nov 1 - Nov 2

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

A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.

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.

5. Devonfield Inn B&B

Lee

$369

$412 total

includes taxes & fees

Nov 2 - Nov 3

A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

A window view of a garden with rocks, bushes, and trees.

A white bench with bright pink cushions, a small potted plant, and decorative wall art including a sun and a crescent moon.

A red door with a wreath, number 5, and flower baskets on either side.

6. The Red Door B&B

Lee

$195

$302 total

includes taxes & fees

Oct 26 - Oct 27

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

A dining table set with a vase of flowers, a book, and cutlery.

7. Brook Farm Inn

Lenox

$205

$237 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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 covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

8. Shaker Mill Inn

West Stockbridge

$126

$138 total

includes taxes & fees

Nov 16 - Nov 17

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

A spacious living room with a high ceiling, wooden beams, a fireplace, and a bookshelf filled with books.

A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

A wooden interior with a table, chair, and a view of a red barn through an open door.

9. Inn at Silver Maple Farm

East Chatham

$174

$195 total

includes taxes & fees

Nov 8 - Nov 9

A dining table with pastries, a coffee pot, and a vase of sunflowers.

A bedroom with a wooden bed, bedside tables, a desk, and a chair.

A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.

A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.

10. Granville House

Housatonic

$254

$284 total

includes taxes & fees

Oct 25 - Oct 26

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

A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

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

Stockbridge

$382

$462 total

includes taxes & fees

Nov 1 - Nov 2

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

A grand hallway with a chandelier, a staircase, and a table with flowers.

A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

A room with a fireplace, two striped armchairs, and a floral drape.

12. Blackberry River Inn

Norfolk

$190

$219 total

includes taxes & fees

Oct 19 - Oct 20

A bedroom with a large bed, a dresser, a chair, and a mirror.

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

13. Wilder House Berkshires

Sheffield

$164

$183 total

includes taxes & fees

Oct 29 - Oct 30

A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

A modern living room with a sofa, armchair, coffee table, and ottoman. There is a large abstract painting on the wall, a dining table with chairs, and a staircase leading to an upper level.

A hallway with a wooden door, a bench, and a staircase.

A garden with a wooden house, a tree, and a person tending to plants.

14. The Trail in Adams - Berkshires’ Art Hotel

Adams

$174

$194 total

includes taxes & fees

Nov 1 - Nov 2

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

A gazebo in a lush garden with flowering plants and a large tree.

A gazebo in a garden with a house in the background.

A room with a large sliding glass door leading to a garden. Inside, there is a table with chairs and a small table with a vase.

15. Harbour House Inn

Cheshire

$254

$268 total

includes taxes & fees

Oct 22 - Oct 23

A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

A covered porch with white railings and rocking chairs.

A two-story building with a flat roof, solar panels, and a small patio area.

A dining room with a wooden table, chairs, a vase with flowers, and red curtains.

16. Locust Tree Bed and Breakfast LLC

East Canaan

$105

$121 total

includes taxes & fees

Oct 18 - Oct 19

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Top landmarks in Lenox

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

Tanglewood Music Center

9.6/10 (457 reviews)

Tanglewood Music Center is 1.3 mi (2 km) from central Lenox, why not stop by during your stay. If you enjoy the show and want to see another, Shakespeare and Company and Berkshire Theatre Festival are both not far.

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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)

If museums are on your list of things to see in Lenox, then you might want to head to The Mount. If you want to see more of the museums in Lenox, Ventfort Hall Mansion and Gilded Age Museum isn't far either.

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A grassy field with a prominent tree and a small house in the distance.

Wyndhurst Golf & Club

8.4/10 (46 reviews)

You might want to practice your swing at Wyndhurst Golf & Club, a golf course located 1.3 mi (2.1 km) from central Lenox. If Wyndhurst Golf & Club doesn't quite scratch your golfing itch, Greenock Country Club is also nearby.

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Shakespeare and Company

9.2/10 (76 reviews)

Shakespeare and Company is 0.6 mi (0.9 km) from central Lenox, why not stop by during your stay. If you enjoy the show and want to see another, Tanglewood Music Center and Berkshire Theatre Festival are both not far.

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Ventfort Hall Mansion and Gilded Age Museum

9.2/10 (65 reviews)

If visiting museums in Lenox are on your list, you might want to check out the upcoming exhibitions at Ventfort Hall Mansion and Gilded Age Museum. If you want to see more of the museums in Lenox, Berkshire Scenic Railway Museum isn't far either.

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Lenox Mountain

10.0/10 (2 reviews)

If you want to stretch your legs and breathe in some fresh mountain air, head out to Lenox Mountain for a bird's-eye view of Richmond.

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Kennedy Park

9.2/10 (86 reviews)

Travelers who enjoy the great outdoors might want to go to Kennedy Park, located 1.6 mi (2.6 km) from central Lenox. Want to stretch your legs some more? Head to The Mount and Pleasant Valley Wilderness Sanctuary, both nearby.

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Lenox Library

9.0/10 (45 reviews)

Lenox Library is worth a visit when in central Lenox.

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Learn more about Lenox

Tucked into the Berkshires, this cultural haven revolves around Tanglewood, where the Boston Symphony Orchestra performs summer concerts under the stars. The Mount offers a glimpse into Edith Wharton's creative world, with gardens as meticulously crafted as her prose. Shakespeare & Company brings the Bard to life in intimate performances that make complex soliloquies feel like overheard conversations. Pleasant Valley Wildlife Sanctuary's hiking trails reveal why creative souls found inspiration here. Kennedy Park's trails accommodate both casual walkers and serious hikers. Ventfort Hall Mansion provides a window into Gilded Age excess, when industrial barons built 'cottages' with dozens of rooms and European craftsmanship.

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About the destination

Spend time appreciating the museums, the live music and the entertainment choices in Lenox. Activities like hiking give you a chance to enjoy the outdoors while you're in town. Take in the local culture of Lenox at Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company. Check out other sights like Lenox Library and Tanglewood Music Center.