Monthly Rentals in Pittsfield

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

Nearby monthly rentals

Guest favorite

Home in Pittsfield

4.85 out of 5 average rating, 106 reviews

A million-dollar view near Killington on 60 acres.

Debbie LynnRating, 5 stars1 month ago

Perfect location for us and what we can to Pittsfield for. We had plenty of room for five of us. Nice to have a bedroom for everyone. Kitchen was equipped to do anything we wanted to as far as cooking etc Close to skiing Loved being on 60 acres. All worked out perfect for all of us

Guest favorite

Cabin in Pittsfield

4.98 out of 5 average rating, 155 reviews

Tiny Vermont Cabin!

KyleRating, 5 stars1 month ago

Cozy, homey, cabin feel. This place was exactly what we wanted for a ski weekend at Killington. Perfect for two! Would stay here again!

Guest favorite

Condo in Killington

5 out of 5 average rating, 18 reviews

Cozy Slopeside Studio at Pico

SamanthaRating, 5 stars3 weeks ago

After being disappointed by the weather (lack of snow), we were SO happy we chose to stay here with Cole and Rachel. We spent most of our time cuddled on the couch watching movies and felt right at home. We loved it!

Superhost

Home in Stockbridge

4.77 out of 5 average rating, 83 reviews

Ski, snow mobile, hiking, fun on slopes & trails!

AndreaRating, 5 stars3 weeks ago

I really enjoyed my time at Dan’s place. I adhered to his instructions to download the driving directions so I had no problem finding the place upon losing service. The home was cozy and comfortable. Dan was an excellent host as he allowed an early check in and he described the place very well.

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 & traveling professionals

Comfortable accommodations for nomadic and remote working professionals with wifi and dedicated work spaces.

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 vacation 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

Traveling professional? Find a long-term stay with high-speed wifi 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

Wifi

Pet friendly

Laptop-friendly workspace

Free parking on premises

Corporate Housing

Stay near Pittsfield's top sights

Clear River Tavern23 locals recommend

Original General Store20 locals recommend

Vermont River Tubing16 locals recommend

Green Mountain Trails16 locals recommend

The Backroom14 locals recommend

White River Golf Course11 locals recommend

Destinations to explore

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