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B&B in Pittsfield

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
Adams
8.8 out of 10, Excellent, (141)
"It was clean and quiet good Breakfast "
United States
William
$174 nightly
The price is $194
Nov 12 - Nov 13
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel

Harbour House Inn

3.5 star property
Cheshire
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
$247 nightly
The price is $262
Dec 10 - Dec 11
Total with taxes and fees
Harbour House Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (372)
"We LOVED our mini getaway at the Chambery Inn. The room was gorgeous, spacious, and very comfortable. The fireplace couldn't have been easier to operate. The jetted tubs were divine with plenty of hot water the towel warmer was a nice bonus. The room was fully stocked with glassware and a corkscrew which was appreciated. We look forward to coming back"
United States
Samuel
$190 nightly
The price is $212
Nov 12 - Nov 13
Total with taxes and fees
Chambery Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (287)
"Great Views & Hospitality"
United States
Gerald
$181 nightly
The price is $202
Nov 13 - Nov 14
Total with taxes and fees
Lakehouse Inn

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (98)
"A first class little inn"
United States
Philip
$263 nightly
The price is $294
Nov 18 - Nov 19
Total with taxes and fees
The Inn at Stockbridge

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
$329 nightly
The price is $367
Nov 12 - Nov 13
Total with taxes and fees
Devonfield Inn B&B

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (434)
"Nice place, easy check in"
United States
Robert
$101 nightly
The price is $111
Nov 12 - Nov 13
Total with taxes and fees
Shaker Mill Inn

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

Lenox
$239 nightly
The price is $306
Nov 12 - Nov 13
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Whistler's Inn Bed & Breakfast

3.5 star property
Lenox
7.8 out of 10, Good, (500)
"We had a wonderful stay. We are so glad we chose this inn. The location is superb…a five-minute walk to the center of Lenox! It is a beautiful inn with a lot of charm, and the staff is warm and friendly. We loved our large room too! Definitely plan on staying here again when we come back to the area! "
United States
Itzhak
$188 nightly
The price is $210
Nov 12 - Nov 13
Total with taxes and fees
Whistler's Inn Bed & Breakfast

Tanglewood Suites

2.5 star property
Stockbridge
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

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$450 nightly
The price is $503
Nov 24 - Nov 25
Total with taxes and fees
33 Main

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1002)
"Very friendly staff. "
United States
Pamela
$164 nightly
The price is $183
Nov 12 - Nov 13
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (87)
"I’m a former travel writer and hotel reviewer at the NY Times Sunday Travel and I’ve been coming to the Berkshires the past decade. This is the hands down the best B&B in the area. The decor, the ambiance, the artistic details, the warm customer service, the made-to-order gourmet breakfast next to a wood-burning fireplace - all make this place so cozy and truly unique. Listen to the jukebox or play billiards in the inn’s great room. Or lounge beneath the heat lamps on its wraparound porch. You...
United States
Lionel
$224 nightly
The price is $250
Nov 21 - Nov 22
Total with taxes and fees
Granville House

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

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!"
United States
Carol Anne
$414 nightly
The price is $462
Nov 27 - Nov 28
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Cozy Carriage House room with a double bed and private balcony

Lenox
$276 nightly
The price is $347
Nov 12 - Nov 13
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony

Experience Timeless Elegance in The Edith Wharton Room!

Lenox
$239 nightly
The price is $306
Nov 13 - Nov 14
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!

Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox
$294 nightly
The price is $368
Nov 12 - Nov 13
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay

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

Lenox
$257 nightly
The price is $326
Nov 17 - Nov 18
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.

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

Lenox
$376 nightly
The price is $459
Nov 12 - Nov 13
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

Lenox
$413 nightly
The price is $500
Nov 12 - Nov 13
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
2,643
Accommodation
35 B&B
Lowest Price
$111
Highest Price
$503

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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