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

Search Stockbridge Bed & 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
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov

Our top choices for Stockbridge bed & breakfast

Front of property

1. 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 AU$732
includes taxes & fees
30 Sept - 1 Oct
The Inn at Stockbridge
A two-story house with a brick entrance and a white facade.

2. 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 AU$890
includes taxes & fees
12 Oct - 13 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 AU$280
includes taxes & fees
1 Oct - 2 Oct
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, (1,001 reviews)
"Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail."
United States
Rosann
The price is AU$251
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A dining table with pastries, a coffee pot, and a vase of sunflowers.

5. 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 AU$437
includes taxes & fees
12 Oct - 13 Oct
Granville House
A two-story building with a sign reading "Chambéry Inn".

6. 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 AU$429
includes taxes & fees
30 Sept - 1 Oct
Chambery Inn
A garden with a white gazebo, a brick pathway, and various plants and flowers.

7. 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 AU$268
includes taxes & fees
1 Oct - 2 Oct
Whistler's Inn Bed & Breakfast
A large, two-story house with a well-maintained lawn and a fence.

8. 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 AU$651
includes taxes & fees
25 Oct - 26 Oct
Devonfield Inn B&B
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

9. 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 AU$389
includes taxes & fees
26 Oct - 27 Oct
Inn at Silver Maple Farm
Interior detail

10. 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 AU$329
includes taxes & fees
29 Oct - 30 Oct
Wilder House Berkshires
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AU$664
includes taxes & fees
30 Sept - 1 Oct
Historic Susan B. Anthony Room - Cozy & Charming Stay
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

12. 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 AU$211
includes taxes & fees
26 Oct - 27 Oct
Blackberry River Inn
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

13. 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 AU$172
includes taxes & fees
12 Oct - 13 Oct
Locust Tree Bed and Breakfast LLC
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 AU$364
includes taxes & fees
18 Oct - 19 Oct
Brook Farm Inn
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

15. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AU$455
includes taxes & fees
27 Oct - 28 Oct
Experience Timeless Elegance in The Edith Wharton Room!
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is AU$455
includes taxes & fees
27 Oct - 28 Oct
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A porch with a white railing, a potted plant, and a view of a garden.

17. 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 AU$726
includes taxes & fees
28 Oct - 29 Oct
Cozy Carriage House room with a double bed and private balcony
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.

18. 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 AU$695
includes taxes & fees
20 Oct - 21 Oct
Elegant Carriage House room with a queen bed and private patio.
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

19. 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 AU$884
includes taxes & fees
25 Oct - 26 Oct
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
A bedroom with a bed, a television, a fireplace, and a window.

20. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is AU$849
includes taxes & fees
30 Sept - 1 Oct
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Wonderful resort"
Ofer 2-night trip
Posted 9 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

Find out more about Stockbridge

Stockbridge B&B information

Number of reviews
3,143
Accommodation
38 B&B
Lowest Price
AU$172
Highest Price
AU$890

Frequently asked questions

Searching for B&Bs in Stockbridge?
If you want to find some accommodation with fewer rooms than the traditional hotel and a more personalised environment, a B&B might be just the right fit for your trip to Stockbridge. A trip to Stockbridge wouldn't be complete without a stop at Norman Rockwell Museum or Mission House if you're someone who could spend hours browsing exhibits.
Why should you consider a B&B versus a traditional hotel?
Every B&B has a unique charm — whether it's a cosy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the little details are what make bed and breakfasts a fun place to get away.
What are the top B&Bs in Stockbridge?
Take a look at 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.
When should I book my B&B in Stockbridge?
When you're planning your escape to Stockbridge, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Stockbridge?
Travellers 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 visit. You should 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. 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