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Check prices for these dates

Next weekend
Jun 27 - Jun 29
In two weeks
Jul 4 - Jul 6
In one month
Jul 18 - Jul 20
In two months
Aug 15 - Aug 17

Compare 16 B&B in Pittsfield with updated reviews, rates, and availability.

Korean Gourmet Stay at Swiss Farm Inn - 1 night
Exterior

Korean Gourmet Stay at Swiss Farm Inn - 1 night

$564 nightly
The price is $632
Jun 22 - Jun 23
Total includes taxes and fees
Korean Gourmet Stay at Swiss Farm Inn - 1 night
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (31)
"Jimmy and John were amazing hosts! Very communicative!"
$179 nightly
The price is $197
Jun 30 - Jul 1
Total includes taxes and fees
Stay At Jimmy's
The Vesper
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (20)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
$165 nightly
The price is $182
Jun 22 - Jun 23
Total includes taxes and fees
The Vesper
The Jackson
Fireplace

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (216)
"What a lovely place to stay. The couple that manage The Jackson are absolutely wonderful and made our stay fabulous. I would highly recommend staying here with gorgeous surroundings, charming rooms and lovely hospitality."
$242 nightly
The price is $266
Jun 25 - Jun 26
Total includes taxes and fees
The Jackson
Echo Lake Inn
Exterior

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Charming place, the food was great, rooms clean, and service was excellent"
$214 nightly
The price is $234
Jun 25 - Jun 26
Total includes taxes and fees
Echo Lake Inn
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (351)
"Such a beautiful and cozy place to stay!! Welcoming atmosphere and people! Had a wonderful time!"
$144 nightly
The price is $159
Jun 29 - Jun 30
Total includes taxes and fees
Snowed Inn
Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (177)
"Beautiful scenery. Accommodating hosts, helpful to move my luggage up and down staircase, even putting into my car when I departed. Excellent made to order breakfast, multiple decaf coffee refills, even preparing a to go coffee in my travel cup. I would definitely stay again when visiting this region. A gem."
$110 nightly
The price is $124
Jun 23 - Jun 24
Total includes taxes and fees
Mountain Valley Retreat
Inn at Neshobe River
Exterior

Inn at Neshobe River

3.0 star property
9.2 out of 10, Wonderful, (11)
"This is a charming BNB. Our room was gorgeous, the bed very comfortable and the breakfast delicious. The inn keepers are delightful and the definition of hospitable and welcoming. The Inns setting is lovely with well kept and lovely grounds. A real bonus is that right next door is a craft beer and wine tasting room. The award winning beer was great!"
$149 nightly
The price is $164
Jun 23 - Jun 24
Total includes taxes and fees
Inn at Neshobe River
The Lilac Inn
Exterior

The Lilac Inn

3.5 star property
9.6 out of 10, Exceptional, (189)
"Great place to Stay 5 STARS"
$218 nightly
The price is $240
Jun 23 - Jun 24
Total includes taxes and fees
The Lilac Inn
The Upper Suites at Chipman Inn- 5 min to Middlebury College's Rikert Outdoor Center
Terrace/patio

The Upper Suites at Chipman Inn- 5 min to Middlebury College's Rikert Outdoor Center

$1,024 nightly
The price is $1,120
Jun 23 - Jun 24
Total includes taxes and fees
The Upper Suites at Chipman Inn- 5 min to Middlebury College's Rikert Outdoor Center
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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Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Pittsfield?
Prices for B&Bs in Pittsfield often vary, but you can find a great deal from $124 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 Bed and Breakfast in Pittsfield?
The most popular time to book a B&B in Pittsfield is during the vibrant summer months, particularly from July to September. This peak season attracts travelers eager to immerse themselves in the region's rich cultural offerings, including art festivals and outdoor concerts. The pleasant weather, with temperatures typically ranging from the mid-60s to the low 80s Fahrenheit, creates an ideal backdrop for exploring the scenic beauty of the Berkshires.
In July, Pittsfield buzzes with activity, as visitors flock to enjoy local attractions such as the Berkshire Museum and the nearby Tanglewood Music Center. The warm days are superb for outdoor activities, including hiking and picnicking in the lush green parks that surround the area. Whether you're wandering through the charming downtown or taking in a live performance, the summer months offer a lively and engaging atmosphere.
For those looking for a more budget-friendly option, November presents a wonderful opportunity to experience the tranquil beauty of Pittsfield. While this month sees fewer tourists, it's the superb time to explore the stunning fall landscapes and enjoy the crisp air without the crowds. You can take leisurely strolls through the picturesque parks, visit local galleries, or indulge in cozy dining experiences at the area's charming restaurants.
What is the difference between a Pittsfield Bed and 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.