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B&B in Pittsfield

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1005)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
$163 nightly
The price is $182
Oct 28 - Oct 29
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, (492)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
$148 nightly
The price is $165
Sep 29 - Sep 30
Total with taxes and fees
Whistler's Inn Bed & Breakfast

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (94)
"What a wonderful one-night stay on the July 4th weekend. It’s a beautiful, comfortable inn with lovely hosts. Also in a great location, set back from a fairly busy country road with several good food options nearby, and charming villages and towns to tour. Highly recommend. "
$209 nightly
The price is $234
Sep 29 - Sep 30
Total with taxes and fees
Inn at Silver Maple Farm

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (427)
"Very casual and easy check in and out; lovely and substantial breakfast"
$165 nightly
The price is $182
Oct 1 - Oct 2
Total with taxes and fees
Shaker Mill Inn

Tanglewood Suites

2.5 star property
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
$269 nightly
The price is $269
Sep 28 - Sep 29
Total with taxes and fees
Tanglewood Suites

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (136)
"We had an excellent experience. The location was convenient for our needs, clean, and tastefully done. It's excellent value for the area. It must be said that a younger traveller will probably be more comfortable with the low-touch approach (text check in, code-locked doors), but they've clearly made an effort to be more accessible to a traveler looking for something more traditional. "
$174 nightly
The price is $194
Sep 28 - Sep 29
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (369)
"ease of late check in. Super comfortable room."
$250 nightly
The price is $279
Sep 28 - Sep 29
Total with taxes and fees
Chambery Inn

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (160)
"Inn was gorgeous and staff exceptional!"
$199 nightly
The price is $222
Sep 29 - Sep 30
Total with taxes and fees
Brook Farm Inn

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (282)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
$180 nightly
The price is $201
Sep 29 - Sep 30
Total with taxes and fees
Lakehouse Inn

Granville House

3.0 star property
10.0 out of 10, Exceptional, (85)
"Beautiful place! Terri and Terry are the best!"
$269 nightly
The price is $300
Oct 13 - Oct 14
Total with taxes and fees
Granville House

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
$335 nightly
The price is $374
Oct 14 - Oct 15
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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!! "
$252 nightly
The price is $267
Sep 29 - Sep 30
Total with taxes and fees
Harbour House Inn

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (129)
"The inn has an excellent location and amenities."
$399 nightly
The price is $446
Sep 29 - Sep 30
Total with taxes and fees
Devonfield Inn B&B

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"This is a beautiful property straight out of a magazine. Service was impeccable"
Inn at Kenmore Hall

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

$232 nightly
The price is $299
Oct 28 - Oct 29
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, (71)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
$613 nightly
The price is $685
Oct 1 - Oct 2
Total with taxes and fees
33 Main

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (69)
"Dahlia is great. Excellent accommodation. We walked to Tanglewood "
Eastgate Inn B&B

Berkshire Mountain House

3.0 star property
9.6 out of 10, Exceptional, (27)
"GORGEOUS Scenery and NICE place to stay !"
Berkshire Mountain House

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
$415 nightly
The price is $464
Sep 28 - Sep 29
Total with taxes and fees
The Inn at Stockbridge

The Red Door B&B

3.0 star property
10.0 out of 10, Exceptional, (5)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
$265 nightly
The price is $297
Oct 27 - Oct 28
Total with taxes and fees
The Red Door B&B
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

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews
2,831
Accommodation
34 B&B
Lowest Price
$165
Highest Price
$685

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 $165 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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