Monthly Rentals in Windsor

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

Nearby monthly rentals

Enter dates and number of guests to see the total trip price including additional fees and taxes, and rounded up to the nearest integer.

Guest favourite
Apartment in Plainfield
4.97 out of 5 average rating, 268 reviews

Sunny, light filled loft in 1873 Colonial

JesseRating, 5 stars1 week ago
I needed a local getaway while some work was being done on my house, and Peter's place was perfect. Comfortable, quiet, clean, and in a beautiful, rural location. Served my needs perfectly, and I will definitely recommend it to visiting friends and family.
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 stars5 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 Hinsdale
5 out of 5 average rating, 13 reviews

Modern Lakehouse with Private Lake Access

ErikRating, 5 stars3 months ago
World travelers here and we loved this house. We were super comfortable with a bedroom for each person and nice bathrooms and kitchen. We wished we could have used the outdoor amenities, but the house was super cozy for a wintry stay. We really appreciated all the supplies, from toiletries and towels, to coffee and a fully stocked kitchen. Great hosts and a great house in the Berkshires.

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.

Stay near Windsor's top sights

Notchview | The Trustees of Reservations19 locals recommend
Wahconah Falls State Park17 locals recommend
Holiday Brook Farm3 locals recommend
*Some exclusions may apply in certain geographies and for some properties.