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 Smithville
4.96 out of 5 average rating, 182 reviews

Private Fishing Spot, Family Fun & Wifi - 10 Acres

SueRating, 5 stars2 days ago
Great place to stay! A bit out of the way, but very well worth it, especially for several days or more! Very simple and welcoming but very, very comfortable and cozy. Everything you needed and more! Great stay!!!
Top guest favorite
Home in La Grange
4.98 out of 5 average rating, 121 reviews

The Modern Mule - Relaxing & stylish cabin escape!

ArmandoRating, 5 stars1 week ago
The house was secluded and not far from major stores or highways. The house was well decorated and furnished allowing us to have all that we needed for the stay. The environment that surrounds the house was a plus being able to be secluded from others due to the location of the house on the property was ideal. The stay was great and Tyler responded to the questions we had. I would highly recommend this airbnb and would stay at this location again.
Top guest favorite
Barn in La Grange
5 out of 5 average rating, 130 reviews

Steelwaters. Contemporary Quonset on forty acres.

BillRating, 5 stars1 month ago
Amazingly helpful. We were in Lagrange for MS 150 ride. Out hosts went way way beyond to help us with the MS 150 ride. We appreciated their hospitality and hope we might be able to reciprocate one day!
Top guest favorite
Farm stay in Paige
4.99 out of 5 average rating, 166 reviews

Shady Paddock Farm-Willow House

PeterRating, 5 stars2 weeks ago
Tammy was incredible when it came to accommodation, we showed up late and made sure that everything was perfect when we arrived. It is so secluded and really ensured that we had everything we needed. We loved everything about this location and just the peace that came with knowing that we were taken care of was incredible! An absolute gem to stay at!

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