Monthly Rentals in Pittsfield

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

Nearby monthly rentals

Guest favorite
Apartment in Pittsfield
5 out of 5 average rating, 6 reviews

Sunny 1 Bedroom Apartment

Jasmine MaeRating, 5 stars3 months ago
We really loved our stay at Carrie's place in Pittsfield. She was a fantastic host: responsive, friendly, and proactive. The apartment is so cozy and well-equipped, and we felt at home right away. My dog absolutely LOVES the backyard, and has spent all winter doing snow zoomies every chance he gets. The area is peaceful, but being close to neighbors makes us feel like we're not isolated. All the everyday necessities we need (groceries, doctors, vets, car repair) are a 3-5 minute drive away, and downtown have a ton of cute shops and cafes. There's also a bunch of great sledding and skiing options nearby, and if we come back in the summer, we're going to be sure to check out the nearby trails. We truly enjoyed our time here and would come back in a heartbeat! Thank you Carrie!
Guest favorite
Apartment in Pittsfield
5 out of 5 average rating, 37 reviews

Comfy Quaint Tavern

MarkRating, 5 stars3 months ago
Amy is a fantastic host and has thought of everything you need while staying here. It’s convenient to everything in town and feels like home.
Guest favorite
Home in Pittsfield
4.95 out of 5 average rating, 20 reviews

Whispering Woods Guest House

James H, JrRating, 5 stars5 months ago
Taylor's space was exactly as described. Decorated so cute and extremely clean. Excellent amenities including well-appointed kitchen, snacks, coffee, tea, robes and slippers. Water pressure (including hot water) more than adequate. Tons of info available for "out of towners" if necessary. Communication was top notch.... accommodating, friendly and practically instantaneous. Would highly recommend. Thank you Taylor and Robert!!!
Superhost
Apartment in Pittsfield
4.8 out of 5 average rating, 44 reviews

Newly Renovated, and Spacious great for family

KelRating, 5 stars2 months ago
Have stayed here before. Will stay again. Fits my needs and Shahs a great host

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.

Stay near Pittsfield's top sights

Hancock Shaker Village59 locals recommend
Berkshire Museum37 locals recommend
Pittsfield State Forest12 locals recommend

Destinations to explore

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