Pittsfield house rentals

We found 738 house rentals — enter your dates for availability

Find spaces that suit your style

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    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any holiday home rentals in Pittsfield?
Pittsfield has 738 holiday home rentals to pick from, including in desirable neighbourhoods like Richmond. Offering more value, space and privacy compared to a hotel room, you'll feel at home in a Stayz house.
How much does it cost to stay in a holiday rental house in Pittsfield?
A number of factors will influence the price of a holiday 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.
When is the best time to rent a holiday house in Pittsfield?
This can all depend on the type of weather you like most, among other factors. Many visitors to The Berkshires book a Pittsfield holiday home rental in July, when the temperature ranges from 15ºC to 27ºC.
Where can I rent a Pittsfield holiday house with great views?
Stay at a holiday 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.
Does Pittsfield have any weekend house rentals?
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 holiday home rental that suits your style.
Are there any pet-friendly house rentals in Pittsfield?
Enjoy your next adventure with your four-legged companion at one of the three pet-friendly holiday 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.
What are the top things to do in Pittsfield?
Planning a memorable trip to Pittsfield means finding cool things that the whole family will enjoy. Tanglewood Music Centre, Jiminy Peak Mountain Resort and National Shrine of the Divine Mercy are just two of the options here. And our holiday home rentals are a fabulous base for your sightseeing activities.
Why should I book my holiday rental house with Stayz?
From houses in quiet countryside areas to those located downtown, Stayz has a wide variety of holiday home rentals to choose from. One of the many reasons to book with us? You won't have to share your space with the owner or anyone else. And with flexible cancellation policies and support before, during and after your holiday, we'll ensure everything goes to plan.