Pittsfield B&B: Find the Best Bed and Breakfast from CA $216

A historic building with classical architecture, a traffic light, and a yellow taxi.

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Our top choices for Pittsfield bed & breakfast

1. Shaker Mill Inn

West Stockbridge

Mervin

CA $241 total

includes taxes & fees

Sep 8 - Sep 9

2. The Cornell Inn, Lenox & The Berkshires

Lenox

Edward

CA $324 total

includes taxes & fees

Sep 3 - Sep 4

3. Inn at Silver Maple Farm

East Chatham

Erdem

CA $216 total

includes taxes & fees

Sep 1 - Sep 2

4. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

CA $247 total

includes taxes & fees

Sep 13 - Sep 14

5. Chambery Inn

Lee

Richard

CA $419 total

includes taxes & fees

Sep 29 - Sep 30

6. The Inn at Stockbridge

Stockbridge

Michele

CA $615 total

includes taxes & fees

Sep 13 - Sep 14

7. The Trail in Adams - Berkshires’ Art Hotel

Adams

Jenna

CA $305 total

includes taxes & fees

Sep 8 - Sep 9

8. Devonfield Inn B&B

Lee

Richard

CA $604 total

includes taxes & fees

Sep 3 - Sep 4

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Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"We were biking in Williamstown area and wanted an overnite stay. The Villagers resort meet everything we needed. Would stay again when we are in the area. Linda K"

Berkshires Untold

10/10 Excellent

"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews	1,610
Accommodation	35 B&B
Lowest Price	CA $216
Highest Price	CA $943

Frequently asked questions

Searching for B&Bs in Pittsfield?

If you're looking for something a little more offbeat than your standard hotel, a stay at a bed and breakfast might be the perfect option for your vacation. If you want to lose yourself exploring fascinating exhibits, you might consider stopping by Berkshire Museum and Hancock Shaker Village while you're in town.

How do you know if a B&B is the right choice for your stay?

With attentive service, opportunities to meet guests from other places, and delectable breakfasts, B&Bs provide a unique setting.

What are the best B&Bs in Pittsfield?

Here are some well-liked B&Bs in the surrounding area: The Cornell Inn, Lenox & The Berkshires: 5.9 mi (9.4 km) from the heart of Pittsfield. Enjoy the free full breakfast and unique décor. Inn at Silver Maple Farm: 11 rooms. 10.9 mi (17.5 km) from the downtown core. Enjoy the free buffet breakfast and designer toiletries. Chambery Inn: 9 rooms. Situated 9.7 mi (15.5 km) from the heart of Pittsfield. Enjoy the private yard and deli. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. 13.8 mi (22.2 km) from the heart of downtown. Enjoy the unique décor and patio area. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: 8 rooms. Located 12.4 mi (19.9 km) from the core of Pittsfield. Enjoy the free full breakfast and outdoor pool.

When should I stay at a B&B in Pittsfield?

When you're dreaming of a getaway to Pittsfield, 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 Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

What is there to do in Pittsfield?

When you want to explore some cultural attractions on your trip, Berkshire Museum and Colonial Theater are worthy sites to check out. You might put Barrington Stage Company and Bousquet Ski Area on your list if you want to see more of the area.

How can I get to and around Pittsfield?

Planning your excursions in and around Pittsfield is easier with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the city center. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pittsfield bed & breakfast

1. Shaker Mill Inn

2. The Cornell Inn, Lenox & The Berkshires

3. Inn at Silver Maple Farm

4. Whistler's Inn Bed & Breakfast

5. Chambery Inn

6. The Inn at Stockbridge

7. The Trail in Adams - Berkshires’ Art Hotel

8. Devonfield Inn B&B

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

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

11. Granville House

12. Brook Farm Inn

13. Experience Timeless Elegance in The Edith Wharton Room!

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

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

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

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

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

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

20. Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Berkshire Mountain Lodge

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

Berkshires Untold

Quality Inn Great Barrington

Hotel On North

The Red Lion Inn

Berkshire Inn

Best Western Plus Berkshire Hills Inn & Suites

Find out more about Pittsfield

Pittsfield B&B information

Frequently asked questions

Explore a world of travel with Expedia

Find a Bed and Breakfast in Pittsfield from CA $216

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pittsfield bed & breakfast

1. Shaker Mill Inn

2. The Cornell Inn, Lenox & The Berkshires

3. Inn at Silver Maple Farm

4. Whistler's Inn Bed & Breakfast

5. Chambery Inn

6. The Inn at Stockbridge

7. The Trail in Adams - Berkshires’ Art Hotel

8. Devonfield Inn B&B

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

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

11. Granville House

12. Brook Farm Inn

13. Experience Timeless Elegance in The Edith Wharton Room!

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

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

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

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

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

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

20. Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Find out more about Pittsfield

Pittsfield B&B information

Frequently asked questions

Explore a world of travel with Expedia