Monthly Rentals in Upperville

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
Home in Upperville
5 out of 5 average rating, 11 reviews

Reynard's Retreat in Upperville

PhilipRating, 5 stars4 months ago
Beautiful house with nice amenities. Master bedroom on main floor allows for privacy. Also, great stay if you bring a dog. Safe backyard fenced area and mud room allow space to feed. Hint - walk up to Trinity Episcopal Church about 1/4 mile away and walk in 30+ acre fields behind the church. Accessible and great for walking.
Guest favourite
Cottage in Middleburg
4.95 out of 5 average rating, 197 reviews

Waterfront Cottage at Goose Creek

Jane BRating, 5 stars2 weeks ago
What a wonderful, peaceful, relaxing home! This is one of the nicest places were we have stayed. The cottage is spotless and comfortable. The location is ideal, minutes from the center of town, yet totally private overlooking Goose Creek. We even had three deer visit us two of our mornings. We will definitely stay here again on our next visit to the area.
Guest favourite
Cottage in Upperville
4.88 out of 5 average rating, 88 reviews

Cozy Country Getaway in the Heart of Upperville

SarahRating, 5 stars1 day ago
We were in town for a wedding and had a great 2 night stay at Jennifer’s house. Communication with Jennifer was easy to and the house was clean and decorated nicely. We appreciated the excellent air conditioning as it was quite hot when we first arrived. The beds were comfortable and there was lots of space - especially in the upstairs bedroom. We were able to walk to the Hunters Head Tavern nearby for a nice lunch and Middleburg was about a 10 minute drive away. We didn’t spend much time in the house since we were busy with wedding activities, but it provided a nice quiet base for the weekend. Thanks Jennifer!
Top Guest favourite
Farm stay in Middleburg
4.97 out of 5 average rating, 88 reviews

The Blacksmith Cottage

JeffreyRating, 5 stars1 week ago
4 Lucky Ducks farm is beautiful and so relaxing. We had a wonderful stay, saw all of the animals, and really loved the property. The location is perfect for Middleburg and easy to get to restaurants in the Plains (12 minutes away). Couldn’t have asked for a better place for a getaways weekend!

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.*

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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?

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