Monthly Rentals in Cheshire

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

Nearby monthly rentals

Superhost
Home in Cheshire
4.85 out of 5 average rating, 214 reviews

19th c. Barn in The Berkshires

JohnRating, 5 stars4 months ago
Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 51 reviews

The Berkshires Hummingbird House

AlexisRating, 5 stars2 months ago
A group of friends and I rented this space for our trip to Berkshire East. This was the perfect space that was a fair distance from the mountain. I really recommend this spot for anything! Ski trips, getaways, etc. We had a blast and Karen was a great host. We will definitely be back!
Guest favourite
Apartment in North Adams
4.88 out of 5 average rating, 277 reviews

River Apartment, walk to MassMOCA and downtown

JayRating, 5 stars6 months ago
Amber is an excellent communicator. The apartment is very well equipped and easy to adapt to. Great location, easy to find and has a dedicated parking spot which is terrific where there is no overnight on street parking. AND we even had fresh eggs from Amber’s hens.
Top guest favourite
Home in Cheshire
4.81 out of 5 average rating, 152 reviews

Large Secluded Berkshire Home

BruceRating, 5 stars6 months ago
We thoroughly enjoyed our stay and the accommodations were exactly as stated, comfortable, roomy, very clean and convenient to amenities. The sleeping accommodations were perfect and the beds were comfortable even for older adults and children. The surroundings were incredibly picturesque, beautiful yard for outdoor activities and lovely mountainous views. The host was very accommodating to our needs and for that we are very thankful. We would definitely stay 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 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

Travelling 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 Cheshire's top sights

Mount Greylock State Reservation Visitor Center23 locals recommend
Mount Greylock State Reservation7 locals recommend
Susan B. Anthony Birthplace Museum6 locals recommend
*Some exclusions may apply in certain geographies and for some properties.