Monthly Rentals in Upperville

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

Nearby monthly rentals

Guest favorite
Farm stay in The Plains
5 out of 5 average rating, 8 reviews

Elegant, Country Capsule: Suite and Stone Kitchen

JackRating, 5 stars3 months ago
Great people, very helpful and responsive in a beautiful setting with a fantastic, large room. I arrived from Texas when a winter storm hit and I am not used to the cold. M was generous with the use of the heat and very accommodating but stepping out to get to the kitchen was chilly. Still it was a great stay in a beautiful setting with an accommodating host.
Guest favorite
Cottage in Middleburg
4.95 out of 5 average rating, 196 reviews

Waterfront Cottage at Goose Creek

RandolphRating, 5 stars1 week ago
Secluded location, nice, quiet and peaceful. There is one house next door but didn’t see or hear anyone the entire time. The property is surrounded by woods and a large creek down below out the back. I have a real Service Dog, Malinois/Lab mix who is also off leash trained and I was able to let her enjoy being a dog for a while roaming the property and woods. The only negative is the lack of window coverings in the bedroom/bath room. To compensate we left the outside lights on at night which worked well to allay our fears. The house was very clean and all of the appliances are quite new and worked very well. The house heater is excellent, the shower has water pressure and hot water for days! The internet and TV worked extremely well and there is good cell phone signal. The road is gravel so a very low clearance sports car might have trouble so don’t bring your Corvette!! The house is less than 10 minutes to downtown Middleburg and has a small Safeway. All in all a great experience.
Top guest favorite
Home in Round Hill Village
5 out of 5 average rating, 16 reviews

Littlefield Farm Cottage

AnnRating, 5 stars3 months ago
Nestled in the beautiful hills of Virginia, this cozy Airbnb cottage provides a perfect private getaway. As you travel down the unpaved country road, you'll find all the conveniences needed for a comfortable stay. The kitchen is well-equipped, making meal preparation a breeze, and there are several restaurants nearby for added enjoyment. The porch offers a relaxing spot to read and watch the farm animals and horses. I stayed for an extended period and highly recommend both the host and this location.
Guest favorite
Cottage in Upperville
4.87 out of 5 average rating, 86 reviews

Cozy Country Getaway in the Heart of Upperville

TracilynRating, 5 stars2 months ago
Great stay if you're looking to do things in the area.

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.

Stay near Upperville's top sights

Hunter's Head Tavern54 locals recommend
The Market at Bluewater Kitchen9 locals recommend
Trinity Episcopal Church4 locals recommend
*Some exclusions may apply in certain geographies and for some properties.
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