Monthly Rentals in Cherry Plain

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

Nearby monthly rentals

Guest favourite
Cottage in Williamstown
4.89 out of 5 average rating, 188 reviews

Cute Cozy Comfy Cottage in the Berkshires

KevinRating, 5 stars3 months ago
This little cottage is very comfortable. Its quiet and peaceful, but also provides easy access to local activities. You can just sit around and enjoy all the nature, or you can take a quick drive into town and go to some high quality museums or eat at a number of local restaurants. Its got a fenced in yard for the dogs as well as a bbq and firepit. This was our second stay and we would highly recommend it.
Top Guest favourite
Holiday home in Williamstown
4.98 out of 5 average rating, 96 reviews

ALL welcome: Lovely 1 BR studio, Berkshires beauty

SamRating, 5 stars3 months ago
The hosts were very helpful in general, and responded immediately to take care of a minor issue we mentioned. The studio in the barn is clean, comfortable, and well set up. It's a great spot for 1-2 people. The only minor complaint (which is out of the host's control) is that my wife and I use Verizon, and the studio was a dead zone for cell service for us [when we needed to make a call, we 'solved' this problem by walking down the driveway towards the road, where we got signal]. Wi-Fi in the studio worked great for computer use and streaming, so that is not an issue, just Verizon cell service. We had a great stay overall!
Guest favourite
Condo in Hancock
4.92 out of 5 average rating, 66 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

ArielRating, 5 starstoday
We stayed at Renee’s place during a summer festival weekend hosted at the mountain and it was perfect for our needs! Comfy bed, good kitchen set up and a nice place for lounging in between festival events. Would definitely stay here again!
Top Guest favourite
Cabin in Stephentown
5 out of 5 average rating, 12 reviews

Stylish Mountain Cabin Close To Jiminy Peak

AyseRating, 5 stars4 months ago
Brianna's place was exceptionally clean (the linens smelled clean and fresh and the bathrooms were spotless) and thoughtfully equipped that we felt right at home. It was also very reassuring that Brianna was very responsive and clear in her documentation about the house and check-in / check-out instructions. I wish we could have stayed for longer! Such a quaint home, in a peaceful location - super close to Jiminy Peak. Would love to visit again!

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