Pittsfield house rentals

Pittsfield has vacation home rentals to pick from, including in desirable neighborhoods like Richmond. Offering more value, space and privacy compared to a hotel room, you’ll feel at home in a Vrbo house.

A number of factors will influence the price of a vacation home rental in Pittsfield, such as the size of the property and how long and when you’re staying. All you have to do is key in your travel dates and preferences to find a house that works with your style and budget.

This can all depend on the type of weather you like most, among other factors. Many visitors to The Berkshires book a Pittsfield vacation home rental in July, when the temperature ranges from 59ºF (15ºC) to 80ºF (27ºC).

Stay at a vacation home rental in Pittsfield and you’ll be waking up to amazing vistas. Some of our most popular rental houses here feature views of historic areas.

Browse our weekend rentals and start packing for a thrilling few days away. Our top tips for booking your ideal house in Pittsfield? Be flexible when searching and adjust your travel dates until you find the vacation home rental that suits your style.

Enjoy your next adventure with your four-legged companion at one of the three pet-friendly vacation home rentals in Pittsfield. These stays feature perks that’ll make your pup feel at home, such as a yard to run around in. Just select the “Pets allowed” filter to find a house that has space for every cherished member of your family.

Planning a memorable trip to Pittsfield means finding cool things that the whole family will enjoy. Tanglewood Music Center, Jiminy Peak Mountain Resort and National Shrine of the Divine Mercy are just two of the options here. And our vacation home rentals are a fabulous base for your sightseeing activities.

Vrbo takes the stress out of finding your dream vacation home rental. Use our filters to narrow your search by nightly price, property type, features and more. Whatever your preference, you’ll always get the entire space for you and whoever you’re vacationing with. Also, our cancellation policies offer peace of mind should your plans change. You’ll get your money back if you cancel your booking within the timeframe specified by the property’s cancellation policy. Plus, our free loyalty program, One Key™, lets you earn and spend OneKeyCash™* on eligible bookings on Vrbo, Expedia and Hotels.com. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Hotels.com, Expedia and Vrbo.