Top B&B in Stockbridge in 2026

A nighttime view of a residential area with houses adorned with holiday lights.

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

In two weeks

In one month

In two months

Our top choices for Stockbridge bed & breakfast

1. The Inn at Stockbridge

Stockbridge

Jodi

12.992.869 ₫ total

includes taxes & fees

22 Sept - 23 Sept

Suite, Private Bathroom (RedBird Suite) | View from room

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

Stockbridge

Philippe

16.255.708 ₫ total

includes taxes & fees

12 Oct - 13 Oct

3. Shaker Mill Inn

West Stockbridge

Mervin

4.880.639 ₫ total

includes taxes & fees

22 Sept - 23 Sept

4. Brook Farm Inn

Lenox

Carrie

5.021.214 ₫ total

includes taxes & fees

22 Sept - 23 Sept

Desk, laptop workspace, iron/ironing board (on request), free WiFi

5. Granville House

Housatonic

Nicole

6.509.964 ₫ total

includes taxes & fees

27 Sept - 28 Sept

6. Chambery Inn

Lee

Alexandra

7.846.509 ₫ total

includes taxes & fees

21 Oct - 22 Oct

7. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

4.289.588 ₫ total

includes taxes & fees

22 Sept - 23 Sept

8. Devonfield Inn B&B

Lee

Sebastien

12.758.186 ₫ total

includes taxes & fees

22 Sept - 23 Sept

9. Inn at Silver Maple Farm

East Chatham

"We had a very pleasant stay at this. Eautiful country property. Check in was smooth and instructions were easy to follow. Our room, in the main building was well appointed. The bed was super comfortable and the amenities were fine. Breakfast was great! Common areas were lovely and inviting, and the s’mores kits in the lobby were just the thing for an evening around the outdoor fire pit. Highly recommend for anyone seeking a serene country setting."

Jody

6.235.994 ₫ total

includes taxes & fees

28 Sept - 29 Sept

10. Wilder House Berkshires

Sheffield

Mark

5.602.593 ₫ total

includes taxes & fees

27 Sept - 28 Sept

11. Blackberry River Inn

Norfolk

Rachel

4.488.105 ₫ total

includes taxes & fees

22 Sept - 23 Sept

12. Locust Tree Bed and Breakfast LLC

East Canaan

Nicholas

3.141.674 ₫ total

includes taxes & fees

22 Sept - 23 Sept

13. The Cornell Inn, Lenox & The Berkshires

Lenox

Rosann

4.908.996 ₫ total

includes taxes & fees

22 Sept - 23 Sept

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Stockbridge Hotel Reviews

Quality Inn Great Barrington

10/10 Excellent

"Very nice stay. Nice town to stay in."

Hotel On North

10/10 Excellent

"My husband and I (both architects) loved the very creative way the original building had been converted to a hotel. The interiors were very imaginatively designed, preserving the original wood flooring and high ceilings, incorporating art, old machinery that had been in the paper mill, and an interesting combination of antique furniture. Parking was easy and the hotel location was an easy walk to many places of interest. We enjoyed dinner at the restaurant on the premises--elegant and tasty. Finally, kudos to the very friendly and helpful staff who were always eager to answer our questions, talk about the building's history, or provide an item we needed. Thanks to you all!"

Berkshires Untold

10/10 Excellent

"I was initially disappointed when I realized the property is a refurbished motel with room access via doors directly to the outside. However, the comfortable and welcoming lobby/bar/lounge area and pristine room with a comfy king size bed more than made up for it. The room also had complimentary, refillable water bottles with glasses (not plastic), and beautiful bathroom with full size shampoo, conditioner, body wash, and body lotion. And finally, there was a wardrobe with shelves to store clothes and shoes and a cushioned chair in the corner with a reading light. This was the most comfortable and well appointed hotel room I've been in. Staff at breakfast and at the bar after dinner were friendly and helpful. Highly recommend, though I prefer the rooms on the 2nd floor."

Find out more about Stockbridge

Stockbridge B&B information

Number of reviews	2,179
Accommodation	27 B&B
Lowest Price	3.141.674 ₫
Highest Price	16.255.708 ₫

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.

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

More ways to book

Book B&B in Stockbridge on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Stockbridge bed & breakfast

1. The Inn at Stockbridge

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

3. Shaker Mill Inn

4. Brook Farm Inn

5. Granville House

6. Chambery Inn

7. Whistler's Inn Bed & Breakfast

8. Devonfield Inn B&B

9. Inn at Silver Maple Farm

10. Wilder House Berkshires

11. Blackberry River Inn

12. Locust Tree Bed and Breakfast LLC

13. The Cornell Inn, Lenox & The Berkshires

Top Stockbridge Hotel Reviews

Quality Inn Great Barrington

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

Hotel On North

The Red Lion Inn

Vacation Village in the Berkshires

Berkshires Untold

Howard Johnson by Wyndham Lenox

Find out more about Stockbridge

Stockbridge B&B information

Frequently asked questions

Explore a world of travel with Expedia

Search B&B in Stockbridge

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Stockbridge bed & breakfast

1. The Inn at Stockbridge

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

3. Shaker Mill Inn

4. Brook Farm Inn

5. Granville House

6. Chambery Inn

7. Whistler's Inn Bed & Breakfast

8. Devonfield Inn B&B

9. Inn at Silver Maple Farm

10. Wilder House Berkshires

11. Blackberry River Inn

12. Locust Tree Bed and Breakfast LLC

13. The Cornell Inn, Lenox & The Berkshires

Top Stockbridge Hotel Reviews

Quality Inn Great Barrington

Find out more about Stockbridge

Stockbridge B&B information

Frequently asked questions

Explore a world of travel with Expedia