20 Best B&B in Stockbridge, MA - Bed and Breakfast from AED 444

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

AED 2,295 total

includes taxes & fees

12 Oct - 13 Oct

2. The Inn at Stockbridge

Stockbridge

Jodi

AED 1,834 total

includes taxes & fees

22 Sep - 23 Sep

3. Shaker Mill Inn

West Stockbridge

Mervin

AED 600 total

includes taxes & fees

21 Sep - 22 Sep

4. The Cornell Inn, Lenox & The Berkshires

Lenox

Rosann

AED 856 total

includes taxes & fees

20 Sep - 21 Sep

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

5. Granville House

Housatonic

Nicole

AED 919 total

includes taxes & fees

27 Sep - 28 Sep

6. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

AED 646 total

includes taxes & fees

21 Sep - 22 Sep

7. Chambery Inn

Lee

Alexandra

AED 1,052 total

includes taxes & fees

27 Sep - 28 Sep

8. Blackberry River Inn

Norfolk

Rachel

AED 608 total

includes taxes & fees

20 Oct - 21 Oct

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Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

8/10 Good

"Very quiet property."

Berkshires Untold

8/10 Good

"Stayed here for overnight after seeing a show at Tanglewood. Very nice hotel. Clean, comfortable, well-run. Although we didn’t have a chance to use it, they have a cozy bar/restaurant/lounge area. Breakfast is offered but not included. Extremely convenient location for Tanglewood and any other activities in the Lenox area. Very good value. I’d stay there again."

The Red Lion Inn

8/10 Good

"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."

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.

Room 1

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. Whistler's Inn Bed & Breakfast

7. Chambery Inn

8. Blackberry River Inn

9. Devonfield Inn B&B

10. Wilder House Berkshires

11. Inn at Silver Maple Farm

12. Experience Timeless Elegance in The Edith Wharton Room!

13. Locust Tree Bed and Breakfast LLC

14. Brook Farm Inn

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

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

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

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

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

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

Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Berkshires Untold

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

Quality Inn Lee - Lenox South

The Red Lion Inn

Quality Inn Great Barrington

The Inn at Stockbridge

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 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. Whistler's Inn Bed & Breakfast

7. Chambery Inn

8. Blackberry River Inn

9. Devonfield Inn B&B

10. Wilder House Berkshires

11. Inn at Silver Maple Farm

12. Experience Timeless Elegance in The Edith Wharton Room!

13. Locust Tree Bed and Breakfast LLC

14. Brook Farm Inn

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

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

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

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

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

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

Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Frequently asked questions

Explore a world of travel with Expedia