20 Best B&B in Stockbridge, MA - Bed and Breakfast from ￥18,514

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

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Our top choices for Stockbridge bed & breakfast

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

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

Stockbridge

Philippe

￥61,239 total

includes taxes & fees

Sep 28 - Sep 29

2. The Inn at Stockbridge

Stockbridge

Jodi

￥67,791 total

includes taxes & fees

Sep 15 - Sep 16

3. Shaker Mill Inn

West Stockbridge

Mervin

￥24,810 total

includes taxes & fees

Sep 14 - Sep 15

4. The Cornell Inn, Lenox & The Berkshires

Lenox

Edward

￥29,005 total

includes taxes & fees

Sep 13 - Sep 14

5. Granville House

Housatonic

Nicole

￥38,363 total

includes taxes & fees

Sep 13 - Sep 14

6. Chambery Inn

Lee

Alexandra

￥46,239 total

includes taxes & fees

Sep 27 - Sep 28

7. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

￥30,365 total

includes taxes & fees

Oct 1 - Oct 2

8. Blackberry River Inn

Norfolk

Rachel

￥25,919 total

includes taxes & fees

Sep 14 - Sep 15

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Top Stockbridge Hotel Reviews

Berkshires Untold

10/10 Excellent

"beautiful place, great staff, would love to go back!"

Little Cat Lodge

10/10 Excellent

"Beautiful and peaceful little lodge with easy access to all the wonderful things in the area (Catamount, Lakes etc..). Pool is very tranquil and each room has Mountain views. The lodge is artfully designed as well, providing a luxury feeling. I only wish 1) the indoor common area was open for guests at any time (but I assume this is a cost/staff issue) 2) there as espessso / coffee/ tea available for guests at a wider ranger of hours (only available at continental breakfast or kureg in room). But these would only be added luxuries and did not materially detract from absolutely delightful stay!!"

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."

Jiminy Peak Mountain Resort

10/10 Excellent

"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"

Find out more about Stockbridge

Stockbridge B&B information

Number of reviews	2,536
Accommodation	38 B&B
Lowest Price	￥18,514
Highest Price	￥91,938

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.

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Check prices for these dates

Our top choices for Stockbridge bed & breakfast

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

2. The Inn at Stockbridge

3. Shaker Mill Inn

4. The Cornell Inn, Lenox & The Berkshires

5. Granville House

6. Chambery Inn

7. Whistler's Inn Bed & Breakfast

8. Blackberry River Inn

9. Devonfield Inn B&B

10. Wilder House Berkshires

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

12. Inn at Silver Maple Farm

13. Locust Tree Bed and Breakfast LLC

14. Brook Farm Inn

15. Experience Timeless Elegance in The Edith Wharton Room!

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

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

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

19. Elegant suite with a king bed, fireplace, and kitchenette.

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

Top Stockbridge Hotel Reviews

Berkshires Untold

Berkshire Mountain Lodge

FairBridge Inn Express

Little Cat Lodge

Vacation Village in the Berkshires

The Yankee Inn

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Holiday Inn Club Vacations Oak 'n Spruce Resort

Jiminy Peak Mountain Resort

Find out more about Stockbridge

Stockbridge B&B information

Frequently asked questions

Explore a world of travel with Expedia

Find Stockbridge Bed And Breakfast

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Stockbridge bed & breakfast

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

2. The Inn at Stockbridge

3. Shaker Mill Inn

4. The Cornell Inn, Lenox & The Berkshires

5. Granville House

6. Chambery Inn

7. Whistler's Inn Bed & Breakfast

8. Blackberry River Inn

9. Devonfield Inn B&B

10. Wilder House Berkshires

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

12. Inn at Silver Maple Farm

13. Locust Tree Bed and Breakfast LLC

14. Brook Farm Inn

15. Experience Timeless Elegance in The Edith Wharton Room!

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

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

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

19. Elegant suite with a king bed, fireplace, and kitchenette.

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

Top Stockbridge Hotel Reviews

Berkshires Untold

Find out more about Stockbridge

Stockbridge B&B information

Frequently asked questions

Explore a world of travel with Expedia