An aerial view of a town with autumn-colored trees, a central green field, and surrounding residential areas.

Book Pittsfield Bed & Breakfast

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Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

Our top choices for Pittsfield bed & breakfast

Exterior

1. Brewster Inn

Brewster Inn
3.5 star property
Dexter
9.2 out of 10, Wonderful, (61 reviews)
"We enjoyed our stay, highly recommend!"
United States
Michael
$179 nightly
The price is $195
Aug 11 - Aug 12
Total with taxes and fees
Brewster Inn
Lake

2. Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast
3.0 star property
Oakland
$277 nightly
The price is $302
Sep 4 - Sep 5
Total with taxes and fees
Pressey House Lakeside Bed & Breakfast
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

Hampton Inn Waterville

Hampton Inn Waterville

10/10 Excellent
"This property was sparkling clean and up to date. The Staff was friendly and helpful. The breakfast was great with a waffle bar, hot cooked oatmeal, eggs and sausage, scones, donuts, etc."
Lito 2-night trip
Posted 1 day ago
Hampton Inn Waterville

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews
61
Accommodation
3 B&B
Lowest Price
$195
Highest Price
$302

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 $195 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.

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