A river surrounded by autumn-colored trees and a forested hill.

Find Stockbridge Bed And Breakfast

  • 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

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

Our top choices for Stockbridge bed & breakfast

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (119 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is ￥81,298
￥98,348 total
includes taxes & fees
Oct 18 - Oct 19
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

2. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (107 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
The price is ￥68,942
￥80,858 total
includes taxes & fees
Oct 1 - Oct 2
The Inn at Stockbridge
A red building with a sign reading "Shaker Mill Inn."

3. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (476 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ￥28,176
￥30,909 total
includes taxes & fees
Oct 1 - Oct 2
Shaker Mill Inn
A snow-covered outdoor area with a patio, seating, and a covered dining area.

4. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail."
United States
Rosann
The price is ￥24,156
￥27,707 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

5. The Red Door B&B

The Red Door B&B
3.0 star property
Lee
10.0 out of 10, Exceptional, (5 reviews)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
United States
Anonymous traveler
The price is ￥27,350
￥43,736 total
includes taxes & fees
Oct 26 - Oct 27
The Red Door B&B
A large, two-story house with a well-maintained lawn and a fence.

6. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
The price is ￥64,364
￥71,894 total
includes taxes & fees
Oct 27 - Oct 28
Devonfield Inn B&B
A dining table with pastries, a coffee pot, and a vase of sunflowers.

7. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (106 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is ￥43,277
￥48,341 total
includes taxes & fees
Oct 14 - Oct 15
Granville House
A two-story building with a sign reading "Chambéry Inn".

8. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (388 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is ￥42,488
￥47,459 total
includes taxes & fees
Oct 18 - Oct 19
Chambery Inn
A garden with a white gazebo, a brick pathway, and various plants and flowers.

9. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (519 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is ￥26,492
￥29,591 total
includes taxes & fees
Oct 5 - Oct 6
Whistler's Inn Bed & Breakfast
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

10. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (117 reviews)
"Very nice hotel."
United States
Erdem
The price is ￥38,408
￥43,017 total
includes taxes & fees
Oct 26 - Oct 27
Inn at Silver Maple Farm
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

11. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is ￥38,943
￥48,183 total
includes taxes & fees
Oct 27 - Oct 28
Experience Timeless Elegance in The Edith Wharton Room!
Interior detail

12. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (67 reviews)
"Perfect little b&b."
United States
Mark
The price is ￥32,479
￥36,279 total
includes taxes & fees
Oct 29 - Oct 30
Wilder House Berkshires
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

13. Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is ￥38,943
￥48,183 total
includes taxes & fees
Oct 27 - Oct 28
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

14. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (174 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is ￥34,809
￥40,141 total
includes taxes & fees
Oct 21 - Oct 22
Brook Farm Inn
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

15. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (222 reviews)
"Great breakfast"
United States
Brian
The price is ￥23,606
￥27,146 total
includes taxes & fees
Oct 28 - Oct 29
Blackberry River Inn
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

16. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (450 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is ￥16,524
￥19,003 total
includes taxes & fees
Oct 4 - Oct 5
Locust Tree Bed and Breakfast LLC
A room with a dark green sofa, a small table with a vase of flowers, a desk with a lamp, and a window with curtains.

17. Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Lenox
The price is ￥60,351
￥73,969 total
includes taxes & fees
Oct 20 - Oct 21
Elegant Carriage House room with a queen bed and private patio.
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

18. Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is ￥65,388
￥85,373 total
includes taxes & fees
Oct 25 - Oct 26
Historic Susan B. Anthony Room - Cozy & Charming Stay
A porch with a white railing, a potted plant, and a view of a garden.

19. Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
The price is ￥113,241
￥147,997 total
includes taxes & fees
Oct 23 - Oct 24
Cozy Carriage House room with a double bed and private balcony
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

20. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
The price is ￥76,722
￥100,307 total
includes taxes & fees
Oct 25 - Oct 26
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Very nice room, great price"
Bill 2-night trip
Posted 2 hours ago
Vacation Village in the Berkshires

Find out more about Stockbridge

Stockbridge B&B information

Number of reviews
Accommodation
 B&B
Lowest Price
Highest Price

Frequently asked questions

Searching for B&Bs in Stockbridge?
If you want to find a place to stay with fewer rooms than a hotel and a cozy environment, a B&B might be a great fit for your vacation to Stockbridge. A trip to Stockbridge wouldn't be complete without a stop by Norman Rockwell Museum or Mission House if you're someone who could spend hours browsing exhibits.
Why would you choose B&Bs instead of traditional hotels?
Every B&B has a unique charm. Whether it's a garden for guests to admire or a beautiful dining room, the little details are what make bed and breakfasts the perfect escape.
What are the top B&Bs in Stockbridge?
Check out these B&Bs in Stockbridge: The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: 8 rooms. Enjoy the free full breakfast and outdoor pool. The Inn at Stockbridge: 14 rooms. Enjoy the free cooked breakfast and designer toiletries.
What's the best time of year to book my B&B in Stockbridge?
When you're planning your stay in Stockbridge, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Stockbridge?
Travelers enjoy Stockbridge for its bars and historic landmarks. If cultural attractions are high on your list, Norman Rockwell Museum and Berkshire Theatre Festival are spots to check out. You might put Naumkeag Museum and National Shrine of the Divine Mercy on your list if you want to see more of the area.
How can I get to and around Stockbridge?
You can map out your trip in and around Stockbridge ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 9.6 mi (15.5 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 20 mi (32.3 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

Explore a world of travel with Expedia