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B&B in Pittsfield

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
9.0 out of 10, Wonderful, (139)
"It was clean and quiet good Breakfast "
United States
William
$156 nightly
The price is $175
Nov 10 - Nov 11
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (52)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
$249 nightly
The price is $264
Nov 26 - Nov 27
Total with taxes and fees
Harbour House Inn
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (371)
"Lovely, unique property with huge rooms! Such a fun place to stay. "
United States
Mary
$190 nightly
The price is $212
Nov 2 - Nov 3
Total with taxes and fees
Chambery Inn
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (287)
"Great Views & Hospitality"
United States
Gerald
$176 nightly
The price is $196
Nov 7 - Nov 8
Total with taxes and fees
Lakehouse Inn
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
$369 nightly
The price is $412
Nov 21 - Nov 22
Total with taxes and fees
Devonfield Inn B&B
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (98)
"A first class little inn"
United States
Philip
$339 nightly
The price is $379
Nov 2 - Nov 3
Total with taxes and fees
The Inn at Stockbridge
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (432)
"Very casual and easy check in and out; lovely and substantial breakfast"
United States
Jamie
$101 nightly
The price is $111
Nov 4 - Nov 5
Total with taxes and fees
Shaker Mill Inn
Tanglewood Suites
2.5 star property
6.4 out of 10, (22)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
United States
Amanda
$219 nightly
The price is $219
Dec 1 - Dec 2
Total with taxes and fees
Tanglewood Suites
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
$239 nightly
The price is $306
Nov 2 - Nov 3
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
33 Main
4.0 star property
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$445 nightly
The price is $498
Nov 23 - Nov 24
Total with taxes and fees
33 Main
Granville House
3.0 star property
10.0 out of 10, Exceptional, (86)
"Wonderful! Will stay again!"
Canada
Rebecca
$225 nightly
The price is $251
Nov 3 - Nov 4
Total with taxes and fees
Granville House
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1002)
"Honestly I just enjoyed being able to relax Play some games in the cute pub and the breakfast was yummy and stuff was inviting and so helpful "
United States
Sandra
$164 nightly
The price is $183
Nov 2 - Nov 3
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (500)
"Cozy spot with very friendly propeietor"
United States
Kyle
$253 nightly
The price is $282
Nov 3 - Nov 4
Total with taxes and fees
Whistler's Inn Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (109)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
$332 nightly
The price is $371
Nov 11 - Nov 12
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Experience Timeless Elegance in The Edith Wharton Room!
$239 nightly
The price is $306
Nov 2 - Nov 3
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
Elegant Carriage House room with a queen bed and private patio.
$257 nightly
The price is $326
Nov 4 - Nov 5
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.
Cozy Carriage House room with a double bed and private balcony
$276 nightly
The price is $347
Nov 2 - Nov 3
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
Historic Susan B. Anthony Room - Cozy & Charming Stay
$294 nightly
The price is $368
Nov 2 - Nov 3
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
$376 nightly
The price is $459
Nov 2 - Nov 3
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
$413 nightly
The price is $500
Nov 2 - Nov 3
Total with taxes and fees
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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
2,635
Accommodation
35 B&B
Lowest Price
$111
Highest Price
$500

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 $111 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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