The Upperville Academy

Entire home in Upperville, Virginia

  1. 10 guests
  2. 4 bedrooms
  3. 5 beds
  4. 3.5 baths
Hosted by Jennifer
  1. Superhost
  2. 12 years hosting

Listing highlights

1-hour drive to Shenandoah National Park

This home is near the national park.

Amazing outdoor space

Guests mention the garden, yard, and outdoor area as highlights.

Designed for staying cool

Beat the heat with the AC and ceiling fan.
The Upperville Academy, once a school for boys before the Civil War, is a beautiful historic home in the heart of town. Built in c 1800, this 4000 SF home was recently renovated, preserving the charm of the period, with lots of modern amenities. It is an ideal place for gatherings with close family and friends. The gardens are exquisite, with 2.5 acres of natural and manicured beauty. Lounge in the formal gardens, the back field or the side patio.

The space
The house is full of light, charm and history

Where you’ll sleep

1 of 2 pages

What this place offers

Garden view
Kitchen
Wifi
Dedicated workspace
Free parking on premises

5 nights in Upperville

Aug 8, 2025 - Aug 13, 2025

Rated 4.93 out of 5 from 72 reviews.

Guest favorite
This home is a guest favorite based on ratings, reviews, and reliability

Overall rating

  1. 5 stars, 94% of reviews
  2. 4 stars, 4% of reviews
  3. 3 stars, 1% of reviews
  4. 2 stars, 0% of reviews
  5. 1 stars, 0% of reviews

Rated 4.9 out of 5 stars for cleanliness

Rated 4.9 out of 5 stars for accuracy

Rated 4.9 out of 5 stars for check-in

Rated 4.9 out of 5 stars for communication

Rated 5.0 out of 5 stars for location

Rated 4.8 out of 5 stars for value

Guest reviews mention

Where you’ll be

Upperville, Virginia, United States
This listing's location is verified and the exact location will be provided after booking.

Meet your host

Superhost
344 reviews
4.91 out of 5 average rating
12 years of hosting
Speaks French and Spanish
Lives in Washington, D.C., District of Columbia
Thoughtful, warm, love traveling to new places and spaces. My most favorite place is Virginia wine country that is a magical getaway from the hectic life of the city.

Jennifer is a Superhost

Superhosts are experienced, highly rated hosts who are committed to providing great stays for guests.

Host details

Response rate: 100%
Responds within an hour
To help protect your payment, always use Airbnb to send money and communicate with hosts.

Things to know

Cancellation policy
House rules
Check-in after 2:00 PM
Checkout before 11:00 AM
10 guests maximum
Safety & property
Carbon monoxide alarm
Smoke alarm