Monthly Rentals in Windsor Jambs

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

Nearby monthly rentals

Top guest favourite
Cabin in Cummington
4.98 out of 5 average rating, 207 reviews

Just Be Cabin

SophiaRating, 5 stars1 month ago
Absolutely beautiful cabin in a quiet, beautiful town. The heating kept the cabin extremely cozy and the surrounding forest was breathtaking. Would recommend to anyone looking for a quiet, simple getaway from the busy city. Also, Stacey was very nice, communicative, and made sure we had everything we could possibly need for our stay. Cannot say enough good things!!!
Top guest favourite
Cabin in Savoy
4.97 out of 5 average rating, 213 reviews

The Camp - 20 Minutes to Berkshire East!

JenRating, 5 stars3 weeks ago
Harold (aka Butch) is a fantastic host! He was there for us whenever we needed him, and even checked in on us during some heavy snow storms to be sure we were ok. The cabin is a charming and cozy space located right on the edge of the forest. So peaceful and beautiful!
Guest favourite
Apartment in Plainfield
4.97 out of 5 average rating, 266 reviews

Sunny, light filled loft in 1873 Colonial

BillyRating, 5 stars1 month ago
My girlfriend and I stayed at Peter's loft for a weekend of winter hiking and snowboarding. The weather didn't cooperate with us that weekend for outdoor activities as a snow storm rolled through which honestly didn't bother us at all because the loft was the perfect place to be snowed in. We had such a great time cooking late breakfasts, cuddling up by the pellet stove watching movies, and even got a chance to brave the cold to check out massMOCA. We didn't see Peter once so it felt very private but he was just a text away. He let us add a night to get in before the storm, he stayed on top of the shoveling (don't know how tbh), and kept us updated on road closures during our checkout. He even has a backup generator incase the power went out. Overall we had a great time in such a clean nice space and would definitely recommend to anyone.
Guest favourite
Home in Hawley
4.93 out of 5 average rating, 14 reviews

Berkshire Basecamp: Hike, Bike, Raft & Relax!

AndrewRating, 5 stars4 months ago
Jacqueline’s place was fantastic — cozy, beautiful, sparklingly cleaned, and in a beautiful location. Highly recommended and hope we can 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.
*Some exclusions may apply in certain geographies and for some properties.