20 Best B&B in Pittsfield, MA - Bed and Breakfast from AED 654

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. The Trail in Adams - Berkshires’ Art Hotel

Adams

Jenna

AED 877 total

includes taxes & fees

7 Sep - 8 Sep

2. Harbour House Inn

Cheshire

Gregory

AED 941 total

includes taxes & fees

7 Sep - 8 Sep

3. Chambery Inn

Lee

Joseph

AED 1,108 total

includes taxes & fees

10 Aug - 11 Aug

4. Devonfield Inn B&B

Lee

Francis

AED 1,596 total

includes taxes & fees

3 Sep - 4 Sep

5. The Inn at Stockbridge

Stockbridge

Michele

AED 1,701 total

includes taxes & fees

7 Sep - 8 Sep

6. Whistler's Inn Bed & Breakfast

Lenox

Mary

AED 654 total

includes taxes & fees

24 Aug - 25 Aug

Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, WiFi (free), individually decorated

7. 33 Main

Lenox

Tatyana

AED 2,930 total

includes taxes & fees

31 Aug - 1 Sep

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

Lenox

AED 1,917 total

includes taxes & fees

16 Aug - 17 Aug

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Top Pittsfield Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"Breakfast was delayed but the late arriving staff worked quickly to restore it. Quality of food was excellent"

Berkshire Mountain Lodge

8/10 Good

"We would come back here, even though there are quirky aspects to it that make it less than ideal. Overall, it's a good spot that seems like it was built in the fifties (has an old school vibe of a classic lodge), though it's only 20 years old.. What we liked: super clean, very spacious, a full kitchen, a comfortable bed, free parking, and a relatively reasonable rate. What needs improvement: We requested a quiet room and were put on the side where there is a noisy street. It was ok with earplugs. There is no housekeeping during the stay, which was fine for 3 nights, but would get old for longer. The door between the bedroom and living room needs to be fixed and didn't close fully. The toilet made a loud, running noise for 2 minutes with each flush. The handle on the fridge door broke off with normal use. We reported all of these, and none were addressed while we were there. The staff said they would send maintenance, but didn't, and didn't mention that they couldn't fix these items. Finally, we were charged a $22 resort fee that was supposed to include coffee. While they have a lovely espresso machine, no decaf was offered. As mentioned, even with the minor drawbacks, and knowing that it's more of a time share kind of place, where there's no sort of concierge service, it has many positive qualities that make it an overall good spot."

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Large rooms … I reserved the suit which was only a little more expensive then a regular room … very clean and well maintained facility … breakfast is good.. staff was helpful. Plenty of parking … Thank tou for a very nice stay. Would certainly like to come back …."

The Red Lion Inn

10/10 Excellent

"Escaped into another world on each floor's hallway-the memorabilia and artwork spoke of an honest, New England history. The atmosphere was perfect for a genuine, original immersion into New England's past and LOVED going up and down the 150yr old elevator! Meals delicious w/excellent service. Only one issue we had: the AC in the room was difficult to adjust and were quite chilled even w/turning the thermostat up to 80 deg!!!!!!!!! as suggested by the front desk. Shall make this a yearly visit!"

Quality Inn Great Barrington

10/10 Excellent

"Very nice front desk staff-courteous, upbeat, helpful. Room was clean but leftover trash in bin and no ice tray in refrigerator. VERY comfortable bed. Train in middle of the night was a throwback experience to a different age-i liked it but some would be frightened of the noise. Excellent location."

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. Shaker Mill Inn: 9 rooms. 9.8 mi (15.8 km) from the downtown core. 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. Inn at Silver Maple Farm: 11 rooms. Located 10.9 mi (17.5 km) from the core of Pittsfield. Enjoy the free buffet breakfast and designer toiletries.

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. The Trail in Adams - Berkshires’ Art Hotel

2. Harbour House Inn

3. Chambery Inn

4. Devonfield Inn B&B

5. The Inn at Stockbridge

6. Whistler's Inn Bed & Breakfast

7. 33 Main

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

9. Shaker Mill Inn

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

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

12. The Cornell Inn, Lenox & The Berkshires

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

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

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

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

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

18. Experience Timeless Elegance in The Edith Wharton Room!

19. Granville House

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

Top Pittsfield Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshire Mountain Lodge

The Yankee Inn

Berkshires Untold

Comfort Inn & Suites East Greenbush - Albany

Berkshire Inn

The Red Lion Inn

Best Western Plus Berkshire Hills Inn & Suites

Quality Inn Great Barrington

Frequently asked questions

Explore a world of travel with Expedia

Search B&B in Pittsfield

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pittsfield bed & breakfast

1. The Trail in Adams - Berkshires’ Art Hotel

2. Harbour House Inn

3. Chambery Inn

4. Devonfield Inn B&B

5. The Inn at Stockbridge

6. Whistler's Inn Bed & Breakfast

7. 33 Main

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

9. Shaker Mill Inn

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

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

12. The Cornell Inn, Lenox & The Berkshires

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

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

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

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

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

18. Experience Timeless Elegance in The Edith Wharton Room!

19. Granville House

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

Top Pittsfield Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

Explore a world of travel with Expedia