Middleburg house rentals

We found 110 house rentals — enter your dates for availability
Discover a selection of 23 homes and other holiday rentals in Middleburg that are perfect for your trip. Holiday rentals offer the best amenities for you and your friends, family or even pets, such as parking and a fireplace. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Find spaces that suit your style

Explore Middleburg house rentals

Image of Private Loft at a Working Show Barn ~ Pets Welcome!
Premier Host

Private Loft at a Working Show Barn ~ Pets Welcome!

Sleeps 4 · 1 bedroom · 1 bathroom
9.6 out of 10
exceptional
(28 reviews)
More information about Private Loft at a Working Show Barn ~ Pets Welcome!, opens in a new tab

Top rated house rentals - Middleburg

Living area
Work trip
10.0 out of 10, Exceptional, 11 reviews
"Perfect comfy home to relax in after long days of work. John and Andrea were great with communication. I highly recommend staying here and will stay again in the future. "
Shannon B.
Shannon B.
Stayed Mar 2025
Cozy 3/2 in Orange Park, Pet Friendly.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value