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

Book Pittsfield Bed & Breakfast

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Pittsfield bed & breakfast

1. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (471 reviews)
"Wonderful place to stay!"
United States
Mervin
$150 nightly
The price is $164
Sep 8 - Sep 9
Total with taxes and fees
Shaker Mill Inn

2. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Lovely people and place. Breakfast was great and so was the room. Highly recommend."
United States
FRED
$183 nightly
The price is $204
Sep 8 - Sep 9
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

3. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (517 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
$177 nightly
The price is $198
Sep 7 - Sep 8
Total with taxes and fees
Whistler's Inn Bed & Breakfast

4. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (115 reviews)
"Very nice hotel."
United States
Erdem
$229 nightly
The price is $256
Sep 8 - Sep 9
Total with taxes and fees
Inn at Silver Maple Farm

5. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (156 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
$161 nightly
The price is $180
Sep 9 - Sep 10
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel

6. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (387 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
$300 nightly
The price is $335
Sep 7 - Sep 8
Total with taxes and fees
Chambery Inn

7. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (106 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
$396 nightly
The price is $442
Sep 13 - Sep 14
Total with taxes and fees
The Inn at Stockbridge

8. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"Excellent food and helpful staff"
United States
Richard
$399 nightly
The price is $446
Sep 8 - Sep 9
Total with taxes and fees
Devonfield Inn B&B

9. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$363 nightly
The price is $416
Sep 8 - Sep 9
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!

10. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (105 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
$275 nightly
The price is $307
Sep 8 - Sep 9
Total with taxes and fees
Granville House

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (116 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
$358 nightly
The price is $399
Sep 28 - Sep 29
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

12. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (173 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
$265 nightly
The price is $299
Sep 20 - Sep 21
Total with taxes and fees
Brook Farm Inn

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$363 nightly
The price is $416
Sep 8 - Sep 9
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
$381 nightly
The price is $436
Sep 8 - Sep 9
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.

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

Cozy Carriage House room with a double bed and private balcony
Lenox
$399 nightly
The price is $457
Sep 8 - Sep 9
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$417 nightly
The price is $477
Sep 8 - Sep 9
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay

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

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
$499 nightly
The price is $571
Sep 8 - Sep 9
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
$536 nightly
The price is $599
Sep 13 - Sep 14
Total with taxes and fees
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

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

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Lenox
$589 nightly
The price is $674
Sep 8 - Sep 9
Total with taxes and fees
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
$589 nightly
The price is $674
Sep 8 - Sep 9
Total with taxes and fees
Elegant suite with a king bed, fireplace, and kitchenette.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Pittsfield Hotel Reviews

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews
3,130
Accommodation
35 B&B
Lowest Price
$164
Highest Price
$674

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Pittsfield?
Prices for B&Bs in Pittsfield often vary, but you can find a great deal from $164 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Pittsfield B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Pittsfield?
The best time to book a B&B in Pittsfield is during the vibrant summer months from June to August. This peak season invites outdoor enthusiasts eager to explore the scenic beauty of the Berkshires, with warm temperatures ranging from the mid-60s to mid-80s Fahrenheit. Visitors can enjoy an abundance of activities, from hiking in the lush forests to sailing on the pristine lakes, all while taking in the stunning landscapes that define this charming area.

July is particularly popular, drawing travelers who appreciate a lively atmosphere. This month features numerous cultural events and festivals, including the renowned Tanglewood Music Festival, where you can enjoy world-class performances in a picturesque outdoor setting. The combination of warm weather and vibrant community activities makes this time ideal for those who thrive on social engagement and cultural experiences.

For those considering a visit during a more budget-friendly time, October presents a fantastic option. During this month, the fall foliage reaches its peak, painting the landscape with vibrant hues of red, orange, and gold. The crisp air and beautiful scenery create a superb backdrop for leisurely walks and photo opportunities, all while avoiding the summer crowds.
What is the difference between a Pittsfield Bed & Breakfast and a hotel?
Every Pittsfield B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Pittsfield B&Bs.

Explore a world of travel with Expedia