Book Pittsfield Bed & Breakfast

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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Compare 3 B&B in Pittsfield with updated reviews, rates, and availability.

Pressey House Lakeside Bed & Breakfast
Exterior

Pressey House Lakeside Bed & Breakfast

3.0 star property
Pressey House Lakeside Bed & Breakfast
Taylor Edes Inn
Front of property

Taylor Edes Inn

3.0 star property
9.6 out of 10, Exceptional, (269)
"Nice restful spot, excellent breakfast"
$149 nightly
The price is $162
Jun 25 - Jun 26
Total includes taxes and fees
Taylor Edes Inn
Brewster Inn
Front of property - evening/night

Brewster Inn

3.5 star property
9.0 out of 10, Wonderful, (60)
"We enjoyed our stay, highly recommend!"
$167 nightly
The price is $182
Jun 25 - Jun 26
Total includes taxes and fees
Brewster Inn
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 $162 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 best time to book a B&B in Pittsfield is during the vibrant fall months of September and October. As the leaves begin to change, this picturesque town offers stunning views of the Berkshires, making it a great backdrop for outdoor activities and leisurely strolls. Travelers can enjoy comfortable temperatures, typically ranging from the mid-40s to the mid-60s Fahrenheit, ideal for exploring nearby hiking trails or taking part in local festivals celebrating the harvest season.
September marks the beginning of a delightful period where visitors can experience the last stretches of warm weather while engaging in activities such as apple picking or visiting charming local markets. The atmosphere is lively yet relaxed, allowing for a stress-free visit filled with delightful experiences.
For those looking for a more budget-friendly option, consider planning your trip in December. This month offers a unique charm with festive decorations and holiday events, providing an opportunity to experience Pittsfield's cozy winter vibes without 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.