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

Search Bed and Breakfast in Pittsfield

  • 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
18 Sept - 20 Sept
In two weeks
25 Sept - 27 Sept
In one month
9 Oct - 11 Oct
In two months
6 Nov - 8 Nov

Our top choices for Pittsfield bed & breakfast

A large, two-story house with a covered front porch and a chimney.

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
The price is S$246
includes taxes & fees
15 Sept - 16 Sept
Brewster Inn
A lakeside property with a small dock, outdoor seating, and a gazebo.

2. Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast
3.0 star property
Oakland
The price is S$349
includes taxes & fees
11 Oct - 12 Oct
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.
View all properties
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

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

8/10 Good
"Exactly as advertised. Perfectly adequate nothing crazy fancy close to everything."
Andree 4-night trip
Posted 3 hours ago
Fireside Inn & Suites Waterville

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews
61
Accommodation
3 B&B
Lowest Price
S$246
Highest Price
S$349

Frequently asked questions

Searching for B&Bs in Pittsfield?
Whether you're on a family holiday and want a small, cosy place to stay, or you're a solo traveller hoping to get some tips from locals, a B&B might be the right choice for your trip. If you're interested in playing some golf on your trip, JW Parks Golf Course is a good spot to get in a game.
Why should you consider a B&B versus a traditional hotel?
B&Bs all have a unique charm — whether it's a picturesque garden or a sunlit breakfast nook, the little details are what make bed and breakfasts a fun place to get away.
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. Enjoy the spa and in-room fireplace. Brewster Inn: 7 rooms. 17.2 mi (27.6 km) from the city centre. Enjoy the free buffet breakfast and private garden.
When should I stay at a B&B in Pittsfield?
When you're planning your getaway to Pittsfield, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Pittsfield are January, March, December and February, with each month seeing an average of 23 cm 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 such as 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) away. Otherwise, you can search for flights to Bangor, ME (BGR-Bangor Intl.), 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.

Explore a world of travel with Expedia