Search B&B in Pittsfield

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

B&B in Pittsfield

Game room
Pine Tree Trail Lodge

Pine Tree Trail Lodge

3.0 star property
Pittsfield
The price is SAR 1,003
SAR 1,633 total
includes taxes & fees
31 Dec - 1 January 2026
Pine Tree Trail Lodge
Front of property - evening/night
Brewster Inn

Brewster Inn

3.5 star property
Dexter
9.2 out of 10, Wonderful, (61)
"So nice with a delicious breakfast every morning."
United States
Melanie
The price is SAR 626
SAR 682 total
includes taxes & fees
7 Dec - 8 Dec
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.
View all properties

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

10/10 Excellent
"The staff was amazing and very kind. The hotel itself is very comfortable, relaxing, and clean. My stay was in a family suite and i had 6 children with me. The staff was so understanding, kind, and hospitable that i instantly felt welcome and was able to relax and enjoy my stay. Thank you so much!"
Stephanie 1-night trip
Posted 3 days ago
Holiday Inn Express & Suites Waterville - North by IHG

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.