Photo by Stephanie Sutton

Search Villas in Middleburg

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 13 Villas in Middleburg with updated reviews, rates, and availability.

Beautiful 2BR Walkout Fenced & Gated Villa, Onsite parking, Pet friendly-2+acres

8.6 out of 10, Excellent, (15)
"We loved Maryland and my son says it’s one of the most beautiful places he’s been. Less than 15 minutes from a charming little town called Potomac with shopping and good food. The property is lovely and the rooms were great. We used the kitchen and watched movies to wind down. Our trip into DC was smooth and the scenery was beautiful. We plan to return in July 2026 and bring the rest of the family. "
Beautiful 2BR Walkout Fenced & Gated Villa, Onsite parking, Pet friendly-2+acres

Beautiful 1BR Walkout Fenced & Gated Villa, Onsite parking, Pet friendly-2+acres

9.2 out of 10, Wonderful, (13)
"Great space for me to sleep and relax for a couple days!"
Beautiful 1BR Walkout Fenced & Gated Villa, Onsite parking, Pet friendly-2+acres

Stunning Former Winery w/ Pool & Mtn Views!

9.4 out of 10, Exceptional, (9)
"This place was perfect for our family and wedding party to all stay together. There was plenty of room, everyone was comfortable, and the scenery was fabulous!"
Stunning Former Winery w/ Pool & Mtn Views!

Private10000sf Retreat GuitarPool Hottub-Wine Area

10.0 out of 10, Exceptional, (21)
"Thank you for making our stay so seamless. We were comfortable and able to have a lot of fun and get a lot accomplished. It’s a great area!"
The price is SAR 3,706
SAR 7,806 total
includes taxes & fees
4 Mar - 5 Mar
Private10000sf Retreat GuitarPool Hottub-Wine Area

Historic Virginia Wine Country Villa w/ Pool, Yard

7.6 out of 10, Good, (15)
"The rooms were very engaging. My daughter-in-law was charmed. We had lots of indoor places in which to play. The pool in the backyard was great for adults & children during the warm summer!"
Historic Virginia Wine Country Villa w/ Pool, Yard

Luxury 4BR Family-Perfect House

Luxury 4BR Family-Perfect House

Magic Hide Aways

10.0 out of 10, Exceptional, (3)
"The host was great to work with. Answered any questions timely. The property was clean and comfortable. Great weekend with family and friends. Many memories made! Easily accessing downtown Manassas area with great restaurants! Would definitely return!"
Magic Hide Aways

Elegant Paris Manor w/ Private Pool!

10.0 out of 10, Exceptional, (1)
"Wonderful property with wonderful people. The Manor house is incredible. The pool and the outdoor space was exactly what we had hoped for. Everyone really enjoyed the wagon ride to the top of the property. Definitely would recommend this family or just a getaway for 2 on a weekend!! John"
Elegant Paris Manor w/ Private Pool!

Elegant Paris Manor w/ Private Pool!

3.0 star property
Elegant Paris Manor w/ Private Pool!

Stunning Former Winery w/ Pool & Mtn Views!

3.0 star property
Stunning Former Winery w/ Pool & Mtn Views!

Historic Virginia Wine Country Villa w/ Pool, Yard

3.0 star property
Historic Virginia Wine Country Villa w/ Pool, Yard
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Middleburg
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Middleburg

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (37)
"The cottage is perfect for a couple. Small, cozy, plenty of room. The heating system takes some learning, but the fireplace is easy. The grounds are beautiful and if the weather cooperates, take the time to walk around them.Proximity to Middleburg and Upperville makes it even better.I hope to return."
The price is SAR 1,031
SAR 1,469 total
includes taxes & fees
18 Mar - 19 Mar
18th Century Stone Cottage minutes from historic Middleburg

Global Luxury Suites at Reston Town Center

3.5 star property
8.2 out of 10, Very Good, (125)
"The location, the building and the property manager, Bushra, were excellent. Lots of local businesses are walkable and a great Reston Town Center location. "
The price is SAR 601
SAR 1,103 total
includes taxes & fees
16 Mar - 17 Mar
Global Luxury Suites at Reston Town Center

Breathtaking views with an indoor private pool, come escape with us

9.8 out of 10, Exceptional, (246)
"We have been coming for six years now and I expect we will come for 20 more. Love this house."
Breathtaking views with an indoor private pool, come escape with us
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Why book your villa in Middleburg with Expedia?
Expedia makes it a breeze to find your dream villa in Middleburg. Traveling with the kids? Use our filters to search for stays with a pool or free WiFi. If you’re on a budget, select how much you’d like to spend and the star rating of the property. We’ll help you find the perfect pad that suits your style and taste.
How can I find cheap villas in Middleburg?
An excellent way to track down cheap villas in Middleburg is with Expedia’s filter tool. Narrow your search results by star rating, budget and amenities to grab unbeatable bargains in only a click or two.