Monthly Rentals in Winchester

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 Winchester
5 out of 5 average rating, 16 reviews

Cameron Corner: King Bed & Office Downtown

MatthiasRating, 5 stars2 months ago
If you come to winchester VA this is the place you want to stay at. The ground floor appartement is absolutely marvellous and we felt like home right away. Jack is very proactive and was so helpful during some crazy winter days, always making sure we're well and taken good care of. The place itself is a little jewel and has everything you need for a short or even, like ours, a several weeks long stay. The kitchen is well equipped and you won't lack anything.
Superhost
Loft in Winchester
4.72 out of 5 average rating, 647 reviews

Immerse yourself in Old Town Winchester (Apt #4)

JimRating, 5 stars1 week ago
I had a great one-night stay! I had a free evening before a work meeting and this spot made it so easy to explore downtown Winchester. It's a stone's throw away from the library (must see for architecture enthusiasts), and literally around the corner from the north end of the Walking Mall. The space was cozy and stocked with the essentials. The bed was super comfortable and the quiet made it easy to sleep. I highly recommend Maureen's place!
Guest favourite
Apartment in Winchester
4.92 out of 5 average rating, 13 reviews

Cameron Grace brand new downtown 1 BR loft

AlexaRating, 5 stars6 months ago
This was a great Airbnb to stay at in the Winchester area! Within walking distance of lots of shops in Old Town, and the host was very accessible.
Superhost
Apartment in Winchester
4.75 out of 5 average rating, 110 reviews

The Blue Door steps from Handley Library

ErikaRating, 5 stars2 months ago
The most convenient stay I have ever had!

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 Winchester's top sights

Shenandoah Valley Discovery Museum20 locals recommend
Bonnie Blue Southern Market & Bakery13 locals recommend
Bright Box Theater3 locals recommend
Washington's Office Museum8 locals recommend
Taste Winchester History21 locals recommend
Union Jack Pub & Restaurant4 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.
  1. Airbnb
  2. United States
  3. Virginia
  4. Winchester
  5. Monthly Rentals