Vacation rentals in Upperville

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Upperville

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Middleburg

4.97 out of 5 average rating, 147 reviews

Modern Home on Middleburg Equestrian Farm

Surprise and delight abound around every corner in this newly renovated, open floor-plan 3 bedroom, 2 bath getaway. Furnished by BoConcept and outfitted with the latest appliances, Gibson House is the ideal getaway for couples or small families looking for a weekend escape with all the comforts of home. Visit with the horses in the adjacent paddocks. Come enjoy wineries, shopping, history, steeplechase racing and polo in Middleburg and the nearby towns of Upperville, The Plains, and Marshall.

Dec 29 – Jan 5

ﺩ.ﺇ1,431 per night
Superhost

Cottage in Upperville

4.87 out of 5 average rating, 111 reviews

Cottage on Pantherskin Creek - Upperville

Newly restored Historic Charity Cottage is nestled on the edge of Upperville, overlooking the Pantherskin Creek. Cottage is private, beautifully decorated, cozy, restored with top craftmanship, and equipped with modern amenities. Surrounded by areas top attractions, including a 5 min. drive to popular Hunters Head Tavern, and 8 miles west of Downtown Middleburg, just to name a few. Whether you are hear for a couples getaway, history buff, or weekend away this cottage is sure to impress.

Apr 28 – May 5

ﺩ.ﺇ834 per night
Guest favorite

Apartment in The Plains

4.97 out of 5 average rating, 439 reviews

Rose End

Need to social distance? Our quiet country studio is far enough from Washington DC to get away without being gone. Ideal for grabbing some space, a long run, a bike ride, or visiting local wineries. The Appalachian Trail is just a stone's throw away. We respect your privacy. No smoking is allowed and internet access is from your own hot-spot. The studio includes a satellite TV, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

Aug 15 – 22

ﺩ.ﺇ324 per night

Popular amenities for Upperville vacation rentals

Stay near Upperville's top sights

Hunter's Head Tavern54 locals recommend
The Market at Bluewater Kitchen9 locals recommend
Trinity Episcopal Church4 locals recommend

Other great vacation rentals in Upperville

Guest favorite

Cottage in Bluemont

4.95 out of 5 average rating, 166 reviews

The Cottage at Stonecroft

Feb 19 – 26

ﺩ.ﺇ509 per night
Guest favorite

Home in Paris

4.97 out of 5 average rating, 301 reviews

Ashby's Perch -- A Very Special Retreat

Nov 19 – 26

ﺩ.ﺇ1,263 per night
Guest favorite

Tiny home in Purcellville

4.96 out of 5 average rating, 309 reviews

Remote Tiny House in Purcellville

Jun 3 – 10

ﺩ.ﺇ525 per night
Guest favorite

Guesthouse in Warrenton

4.98 out of 5 average rating, 247 reviews

The Alton Cottage -a luxury country retreat

Jun 16 – 23

ﺩ.ﺇ537 per night
Guest favorite

Home in Middleburg

4.86 out of 5 average rating, 248 reviews

super cosy cottage with high speed internet

Jun 9 – 16

ﺩ.ﺇ1,053 per night
Guest favorite

Farm stay in Round Hill

4.94 out of 5 average rating, 340 reviews

Come and get your goat on!

Jun 22 – 29

ﺩ.ﺇ563 per night
Guest favorite

Farm stay in Middleburg

4.9 out of 5 average rating, 91 reviews

Self-contained apartment on Organic vegetable farm

Dec 12 – 19

ﺩ.ﺇ558 per night
Guest favorite

Farm stay in Upperville

4.99 out of 5 average rating, 67 reviews

The Ark in Upperville

May 4 – 11

ﺩ.ﺇ556 per night
Guest favorite

Cottage in Upperville

5.0 out of 5 average rating, 77 reviews

Lanham House - Fully Restored Upperville Gem

Nov 26 – Dec 3

ﺩ.ﺇ1,068 per night
Guest favorite

Home in Upperville

4.95 out of 5 average rating, 41 reviews

Peaceful Country Retreat

Dec 22 – 29

ﺩ.ﺇ1,086 per night
Guest favorite

Guesthouse in Middleburg

5.0 out of 5 average rating, 39 reviews

18th Century Middleburg Cottage

Feb 18 – 25

ﺩ.ﺇ923 per night
Guest favorite

Cottage in Paris

4.92 out of 5 average rating, 87 reviews

Quaint cottage in historical town of Paris VA!

Jul 14 – 21

ﺩ.ﺇ596 per night

Quick stats about vacation rentals in Upperville

Total rentals

10 properties

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

10 properties include access to wifi

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

510 reviews

Nightly prices starting at

ﺩ.ﺇ734 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Fauquier County
  5. Upperville