Search Guest Houses in Pittsfield

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 1 - Aug 3
In two weeks
Aug 8 - Aug 10
In one month
Aug 22 - Aug 24
In two months
Sep 19 - Sep 21

Guest Houses in Pittsfield

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore
Property grounds

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore

2.0 star property
10.0 out of 10, Exceptional, (10)
"This place is so peaceful and very cozy. Great place for a family to have a nice getaway. The host was super nice and very responsive. "
$461 nightly
The price is $502
Jul 24 - Jul 25
Total includes taxes and fees
Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore
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.
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

The Elmwood

The Elmwood

10/10 Excellent
"Clean, recently renovated rooms. Super friendly staff! Continental breakfast was fresh & eating area was clean & welcoming. Will definitely stay again!"
Anonymous traveler 1-night trip
Posted 23 hours ago
The Elmwood

Frequently asked questions

What is the nightly rate for a guest house in Pittsfield?
Rates for Pittsfield guest houses vary, but travelers can find great-value prices from $502 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Pittsfield guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Pittsfield guest house and a B&B?
A guest house in Pittsfield is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.