Monthly Rentals in Winchester

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

Nearby monthly rentals

Top guest favorite
Home in Winchester
5 out of 5 average rating, 12 reviews

Gorgeous Lakefront! Pool, Games, Fire Pit, Marina!

KaleighRating, 5 stars2 months ago
Leigh was amazing! The home was beautiful and she was so communicative and sweet. We will absolutely be back!
Top guest favorite
Apartment in Winchester
4.96 out of 5 average rating, 28 reviews

Unbeatable Charm & Convenience On The Square!

Jorge L.Rating, 5 stars2 weeks ago
Adam was very responsive and provided clear instructions. Eveything was easier due to his guidance. Some of the outlets didn't work, but the ones that did were enough for the electronics I had. While parking wasn't free at the location, there were plenty of free parking spots on the streets around the building, so that wasn't an issue. Overall, 5/5 it was a quiet, clean place. What makes this 5 stars is for me is Adam himself.
Guest favorite
Home in Winchester
4.93 out of 5 average rating, 55 reviews

Basecamp Retreat TimsFordLake

SharonRating, 5 stars1 week ago
This home was beautiful and comfortable. Perfectly fitted with everything you need and more! The greened in back porch was heaven. The only tiny thing- I wish I had read closer bc while the house was on the lake, you don’t have direct access to walk to the water from the yard as I originally thought. By no means did it ruin the stay, that would have just made it absolutely perfect. Wonderful house, very easy to deal with and helpful owner, definitely recommend!!
Superhost
Apartment in Winchester
4.84 out of 5 average rating, 45 reviews

Just Around the Corner

SarahRating, 5 stars1 month ago
Bring from a costal town, I have never had so much trouble trying to find a spot to swim. Drove around Tim's Ford and still didn't find an actual swimming spot, they have a swimplex in Winchester just minutes away, but I was looking to float in a lake, never found that. . Internet didn't work the first two days of my week stay, the husband came and tried to troubleshoot on first day, without success, I ended up getting it to work the next day. Very welcoming, house is much bigger than in the photos. quite neighbors, didn't hear them once. only complaint is the neighbors dog would be let outside for hours and just bark. 9/10 will 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

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.