10/10 Excellent
Karuna P.
1 Aug 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house
Karuna P.
Stayed 2 nights in Jul 2025
Entire home
Historic spacious home in the heart of Upperville, VA
Photo gallery for Historic spacious home in the heart of Upperville, VA
Reviews
10 out of 10
Exceptional
4 bedrooms3+ bathroomsSleeps 10
Popular amenities
Explore the area
Upperville, VA
- Place, Upperville Park11 min walk
- Place, Fair Oaks Mall46 min drive
- Place, Hollywood Casino at Charles Town Races48 min drive
- Airport, Washington, DC (IAD-Washington Dulles Intl.)44 min drive
Rooms & beds
4 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Bedroom 3
2 Double Beds
Bedroom 4
1 Single Bed and 1 Double Sofa Bed
3 bathrooms, 1 half bathroom
Bathroom 1
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Bathroom 2
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer
Bathroom 3
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Bathroom 4
Soap · Towels provided · Bathtub
Spaces
Kitchen
Outdoor play area
Garden
About this property
Historic spacious home in the heart of Upperville, VA
The Upperville Academy, once a school for boys before the Civil War, is a beautiful, historic home in the heart of Upperville. Built in c1800, this 4000 SF home was recently renovated, preserving the charm of the period, with lots of modern amenities and careful appointments. It is an ideal place for gatherings with close family and friends. The garden is exquisite with 2.5 acres of natural and manicured beauty. The house is full of light, charm and history.
Recent reviews include:
"Our family enjoyed staying at this lovely home in a historic town. There was plenty of room for us to spread out and relax. The house is dog friendly with a fenced-in garden It is absolutely beautiful. The wineries in the area are a fun afternoon diversion and we also picked fruit at a nearby farm."
Another guest wrote:
"This was the most beautiful rental I have stayed at, and also one of the most functional in terms of dishes and having furniture. You can tell the host loves this property. It's an old house that's been very thoughtfully maintained, expanded and furnished. It was the perfect place for a team of bridesmaids to stay."
Recent reviews include:
"Our family enjoyed staying at this lovely home in a historic town. There was plenty of room for us to spread out and relax. The house is dog friendly with a fenced-in garden It is absolutely beautiful. The wineries in the area are a fun afternoon diversion and we also picked fruit at a nearby farm."
Another guest wrote:
"This was the most beautiful rental I have stayed at, and also one of the most functional in terms of dishes and having furniture. You can tell the host loves this property. It's an old house that's been very thoughtfully maintained, expanded and furnished. It was the perfect place for a team of bridesmaids to stay."
Our prices include all fees. No hidden fees.
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Historic house in Upperville! Wineries, equestrian events, great location!
Historic house in Upperville! Wineries, equestrian events, great location!
- Washing machine
- Dryer
- Air-conditioning
10.0 out of 10, Exceptional, (31 reviews)
House Rules
Check in after 2:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
About the area
Upperville
Upperville is home to this holiday home. National Sporting Library & Museum and Museum of Hounds & Hunting North America are cultural highlights, and some of the area's activities can be experienced at RdV Vineyards and Delaplane Cellars. Paris Barns and Northern Fauquier Community Park are also worth visiting.
Upperville, VA
What's nearby
- Upperville Park - 11 min walk - 0.9 km
- Fair Oaks Mall - 46 min drive - 78.7 km
- One Loudoun - 47 min drive - 59.4 km
- Reston Town Center - 47 min drive - 62.2 km
- Hollywood Casino at Charles Town Races - 48 min drive - 64.4 km
Getting around
Restaurants
- Hunter's Head Tavern - 2 min walk
- The Ashby Inn & Restaurant - 7 min drive
- Three Fox Vineyards & Brewery - 14 min drive
- RdV Vineyards - 11 min drive
- Delaplane Cellars - 14 min drive
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
10/10 Excellent
Vonda F.
29 May 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful place
Vonda F.
Stayed 2 nights in May 2024
10/10 Excellent
Somerset G.
29 Jul 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
A wonderful house
Somerset G.
Stayed 3 nights in Jul 2024
10/10 Excellent
Ann P.
7 Nov 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Ann P.
Stayed 3 nights in Oct 2025
10/10 Excellent
Jennifer H.
6 Jan 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Jennifer H.
Stayed 2 nights in Nov 2024
About the host
Hosted by Jennifer Clinton
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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