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Our top choices for Pittsfield bed & breakfast

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, (151 reviews)
"Incredible staff, free parking and cute rooms!"
Canada
Priscilla
$193 nightly
The price is $215
Jun 18 - Jun 19
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
$227 nightly
The price is $240
Jul 1 - Jul 2
Total with taxes and fees
Harbour House Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (378 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
$185 nightly
The price is $207
Jun 18 - Jun 19
Total with taxes and fees
Chambery Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
$389 nightly
The price is $435
Jun 19 - Jun 20
Total with taxes and fees
Devonfield Inn B&B

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
$379 nightly
The price is $424
Jun 23 - Jun 24
Total with taxes and fees
The Inn at Stockbridge

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
$187 nightly
The price is $209
Jun 18 - Jun 19
Total with taxes and fees
Whistler's Inn Bed & Breakfast

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$298 nightly
The price is $341
Jun 18 - Jun 19
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$639 nightly
The price is $714
Jul 1 - Jul 2
Total with taxes and fees
33 Main

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (7 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
$242 nightly
The price is $270
Jun 18 - Jun 19
Total with taxes and fees
The Berkshire Mountain Inn

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
$438 nightly
The price is $501
Jul 6 - Jul 7
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$298 nightly
The price is $341
Jun 18 - Jun 19
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
$163 nightly
The price is $182
Jun 18 - Jun 19
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$390 nightly
The price is $446
Jun 21 - Jun 22
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay

Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
$408 nightly
The price is $467
Jun 29 - Jun 30
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
$511 nightly
The price is $571
Jun 22 - Jun 23
Total with taxes and fees
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

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
$474 nightly
The price is $542
Jun 22 - Jun 23
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

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
$566 nightly
The price is $648
Jun 22 - Jun 23
Total with taxes and fees
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
$562 nightly
The price is $643
Jun 18 - Jun 19
Total with taxes and fees
Elegant suite with a king bed, fireplace, and kitchenette.

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (102 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
Jun 21 - Jun 22
Total with taxes and fees
Granville House

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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
$350 nightly
The price is $391
Jul 1 - Jul 2
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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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Top Pittsfield Hotel Reviews

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews
1,894
Accommodation
34 B&B
Lowest Price
$182
Highest Price
$714

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 $182 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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