Search B&B in Pittsfield

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Pittsfield bed & breakfast

Private kitchen
Pine Tree Trail Lodge

Pine Tree Trail Lodge

Pine Tree Trail Lodge
3.0 star property
Pittsfield
The price is AED 982
AED 1,598 total
includes taxes & fees
11 Jan - 12 January 2026
Pine Tree Trail Lodge
Front of property - evening/night
Brewster Inn

Brewster Inn

Brewster Inn
3.5 star property
Dexter
9.2 out of 10, Wonderful, (61)
"We enjoyed our stay, highly recommend!"
United States
Michael
The price is AED 613
AED 668 total
includes taxes & fees
12 Jan - 13 January 2026
Brewster Inn
Exterior
Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast
3.0 star property
Oakland
The price is AED 1,040
AED 1,134 total
includes taxes & fees
11 Jan - 12 January 2026
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

Pine Tree Trail Lodge

Pine Tree Trail Lodge

10/10 Excellent
"Great place. The host so helpful. I would definitely stay here again. "
Amber G. 4-night trip
Posted 4 days ago
Pine Tree Trail Lodge

Frequently asked questions

Searching for B&Bs in Pittsfield?
Whether you're on a romantic vacation and want to stay somewhere quiet, or you're a solo traveler hoping to meet fellow tourists, B&Bs can be a great choice for many travelers. If you're interested in playing some golf on your trip, JW Parks Golf Course is a good spot to tee off.
Why consider B&Bs instead of traditional hotels?
Every B&B has its own unique feel. Whether it's a comfy common area with a fireplace or a sunlit breakfast nook, the tiny details are what make bed and breakfasts the perfect escape.
What are the best B&Bs in Pittsfield?
Here are some B&Bs in the surrounding area: Pine Tree Trail Lodge: 5 rooms. 0.4 mi (0.7 km) from the heart of Pittsfield.Brewster Inn: 7 rooms. 17.2 mi (27.6 km) from the downtown core. Enjoy the free buffet breakfast and private yard.
When is the best time to book my B&B in Pittsfield?
When you're planning your stay in Pittsfield, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 24°F. The snowiest months in Pittsfield are January, March, December, and February, with each month seeing an average of 9 inches of snowfall.
What is there to do in Pittsfield?
When you want to explore some things to do in Pittsfield, consider a visit to JW Parks Golf Course. You might also consider a trip to sites like Sebasticook Lake or Skowhegan State Fairgrounds if you have time to see more of the area.
How can I get to and around Pittsfield?
Mapping out your trip in and around Pittsfield is easy with these transportation options. Fly into Waterville, ME (WVL-Robert Lafleur), which is located 22.6 mi (36.3 km) from the heart of the city. You can also search for flights into Bangor Intl. Airport (BGR), which is 27.9 mi (44.8 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.