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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Pittsfield bed & breakfast

A snow-covered outdoor area with a patio, seating, and a covered dining area.

1. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,003 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
$178 nightly
The price is $198
Nov 11 - Nov 12
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
A red building with a sign reading "Shaker Mill Inn."

2. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (483 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
$145 nightly
The price is $159
Nov 12 - Nov 13
Total with taxes and fees
Shaker Mill Inn
A garden with a white gazebo, a brick pathway, and various plants and flowers.

3. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.2 out of 10, Very good, (522 reviews)
"Delightful experience in a gilded age setting."
United States
George
Whistler's Inn Bed & Breakfast
A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

4. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
$164 nightly
The price is $184
Dec 3 - Dec 4
Total with taxes and fees
Inn at Silver Maple Farm
Front of property

5. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (110 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
$255 nightly
The price is $285
Nov 15 - Nov 16
Total with taxes and fees
The Inn at Stockbridge
A crowded outdoor event with tents and people gathered in a grassy area.

6. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (390 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
$194 nightly
The price is $217
Nov 22 - Nov 23
Total with taxes and fees
Chambery Inn
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

7. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
$369 nightly
The price is $412
Nov 13 - Nov 14
Total with taxes and fees
Devonfield Inn B&B
A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

8. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.2 out of 10, Wonderful, (159 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
$173 nightly
The price is $193
Dec 11 - Dec 12
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$295 nightly
The price is $338
Nov 11 - Nov 12
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A two-story house with a brick entrance and a white facade.

10. 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
9.4 out of 10, Exceptional, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
$414 nightly
The price is $462
Nov 26 - Nov 27
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

11. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.6 out of 10, Exceptional, (178 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
$165 nightly
The price is $187
Nov 11 - Nov 12
Total with taxes and fees
Brook Farm Inn
A dining area with a round table and four chairs, a radiator, and a window with a view of greenery.

12. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (110 reviews)
"We loved everything about Granville House, especially the innkeepers! Wonderful atmosphere and excellent food! It was definitely the highlight of our trip to New England."
United States
Cynthia
$254 nightly
The price is $284
Nov 20 - Nov 21
Total with taxes and fees
Granville House
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

13. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$295 nightly
The price is $338
Nov 15 - Nov 16
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
A porch with a white railing, a potted plant, and a view of a garden.

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

Cozy Carriage House room with a double bed and private balcony
Lenox
$328 nightly
The price is $376
Nov 15 - Nov 16
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
A room with a dark green sofa, a small table with a vase of flowers, a desk with a lamp, and a window with curtains.

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
$310 nightly
The price is $355
Nov 15 - Nov 16
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$345 nightly
The price is $395
Nov 11 - Nov 12
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

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
$425 nightly
The price is $487
Nov 12 - Nov 13
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
A modern living room with a sloped ceiling, a sofa, a coffee table, and a unique chandelier.

18. 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
$509 nightly
The price is $583
Nov 15 - Nov 16
Total with taxes and fees
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
A bedroom with a bed, a television, a fireplace, and a window.

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
$457 nightly
The price is $511
Nov 12 - Nov 13
Total with taxes and fees
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
A modern living room with a sofa, a coffee table, and a fireplace.

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
$509 nightly
The price is $583
Nov 11 - Nov 12
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.
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Learn more about Pittsfield

Nestled in the heart of the Berkshires, this cultural hub boasts the renowned Berkshire Museum and historic Colonial Theatre. Outdoor enthusiasts can hike nearby Pittsfield State Forest trails before exploring the vibrant downtown's farm-to-table restaurants and local art galleries.

See all hotels in Pittsfield
A historic building with a clock, a flag, and a street lamp.

Top reviews in Pittsfield

A red building with a sign reading "Shaker Mill Inn."
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...
United States
Joe
Reviewed February 27, 2022
Shaker Mill Inn

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 $159 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.

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