Monthly Rentals in Windsor County

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

Nearby monthly rentals

Top guest favorite
Chalet in Woodstock
4.98 out of 5 average rating, 105 reviews

Falcon House: VT Chalet w/Sauna, Bike to Village

VanessaRating, 5 stars1 month ago
Enjoyed everything about our stay. Beautiful property, loved the sauna and ability to snowshoe right out the door. Quaint and nicely decorated. Plenty of privacy, room for guests including extra parking. Had nearly 12 inches of snow while there, quite the winter wonderland. Quickly plowed, shoveled and sanded when needed. Oversized windows and unique architecture made it all extra special. Will definitely return. Perfect for any season.
Top guest favorite
Home in Woodstock
5 out of 5 average rating, 47 reviews

Hiker’s Hygge on 21 Acres and Aqueduct Trails

PhoebeRating, 5 stars1 month ago
Kevin and Emily's home offers a cozy launching point for adventures around Woodstock and the upper valley area, with a setting that is incredibly peaceful and picturesque. Kevin was very clear with directions and extremely responsive while we were staying at the house. He also generously agreed to a delayed checkout, so my daughter and her friend could enjoy a last dose of winter fun before our departure. The house had everything we needed, including two sledding saucers for snow play, and a gas stove to warm up next to after coming in from the cold. One small detail to note--the lower bunk bed has a low/confined ceiling that can be tricky for taller kiddos. Overall, we had a lovely stay and would definitely come back to explore the trails in another season!
Top guest favorite
Cottage in Windsor
4.97 out of 5 average rating, 383 reviews

Ogden's Mill Farm

LaurenRating, 5 stars3 days ago
Our family enjoyed our stay immensely. Our boys (7&10) loved playing with the dogs outside and throwing sticks for them. Scenery and land were stunning. It was peaceful, clean and the beds were comfortable. Can’t wait to go back.
Top guest favorite
Cottage in Hartland
4.97 out of 5 average rating, 455 reviews

Breeze Hill Cottage

OlesjaRating, 5 stars2 months ago
Very comfortable place, clean and easy to get to. Beautiful view of rising sun from kitchen and living room area. Loved watching birds from the kitchen window while drinking my coffee in the morning. Kitchen is equipped with everything you need to make a great dinner or breakfast. Thank you!

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.

Destinations to explore

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