Monthly Rentals in Pittsfield

Discover long-term rentals that feel like home, for stays of a month or longer.

Nearby monthly rentals

Enter dates and number of guests to see the total trip price including additional fees and taxes, and rounded up to the nearest integer.

Superhost

Guesthouse in Pittsfield

4.74 out of 5 average rating, 23 reviews

Private Guesthouse Kitchen Washer Dryer Dishwasher

LoganRating, 5 stars1 month ago

Great place that I stayed at for a night. I enjoyed it, had everything you could need. James was very welcoming and I appreciated being able to stay.

Guest favourite

Home in Winchester

4.91 out of 5 average rating, 140 reviews

Winchester Guest Cottage

PRating, 5 stars1 week ago

Only stayed one night but Anthony very accommodating. Enjoyed the friendly small town vibe and neighborhood. Peaceful. Thanks again!

Top Guest favourite

Home in Griggsville

4.9 out of 5 average rating, 92 reviews

Arrowhead Farmhouse, Spacious home, scenic views

JessRating, 5 stars1 month ago

This was our second stay at Sarah’s home. It was even better than the first time! The family felt right at home as we did the first time. I would highly suggest the front porch for morning coffee and the property is fantastic for a morning walk as well. Plenty of room for the kiddos to play outside. They are great hosts and I would highly recommend! 😊

Guest favourite

Home in Pittsfield

4.84 out of 5 average rating, 236 reviews

Florence Guest House

LoriRating, 5 stars2 weeks ago

My two sisters and I enjoyed our stay. It was so comfortable and homey and had everything we needed. I especially loved the very hot water in the shower and the heater in the ceiling above the shower.

Explore all

The comforts of home and great monthly rates

Fully furnished rentals

From peaceful mountain cabins to convenient urban apartments these furnished rentals have all the amenities of home.

Digital nomads & travelling professionals

Comfortable accommodation for nomadic and remote working professionals, with Wi-Fi and dedicated workspaces.

Delight included

Sometimes the destination is the accommodation. From cliffside cabins to tranquil houseboats, these rentals are full of unique features.

Pets welcome

Discover places to stay that accommodate pets, so you can bring your four-legged friend along.

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term holiday rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Travelling professional? Find a long-term stay with high-speed Wi-Fi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.

Popular amenities for monthly rentals

Kitchen

Wi-Fi

Pet friendly

Laptop-friendly workspace

Free parking on premises

Corporate Housing

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.