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Historic spacious home in the heart of Upperville, VA

Photo gallery for Historic spacious home in the heart of Upperville, VA

A garden with a pergola, various flowering plants, and trees in the background. - Historic spacious home in the heart of Upperville, VA (Upperville)
A spacious living room with a white sofa, a coffee table, and a fireplace. There is a piano in the background and a door leading to another room. - Historic spacious home in the heart of Upperville, VA (Upperville)
A porch with a blue carpet, white railing, and blue rocking chairs. - Historic spacious home in the heart of Upperville, VA (Upperville)
A bedroom with a bed, a desk, a chair, a television, and a window with curtains. - Historic spacious home in the heart of Upperville, VA (Upperville)
A grand piano in a spacious living area with a wooden floor and a white staircase. - Historic spacious home in the heart of Upperville, VA (Upperville)
At Historic spacious home in the heart of Upperville, VA , you can look forward to a garden, a playground, and laundry facilities. Guests can connect to free in-room WiFi.

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

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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."

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About the area

Upperville is home to this vacation 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 Bamboo Maze are also worth visiting. Visit our Upperville travel guide
View more Vacation homes in Upperville
Map
Upperville, VA

What's nearby

  • A town with a church, a river, and a bridge.
    Harpers Ferry National Historical Park
    50 min drive - 69.0 km
  • Upperville Park
    11 min walk - 1.0 km
  • Jiffy Lube Live
    43 min drive - 60.7 km
  • Hollywood Casino at Charles Town Races
    49 min drive - 65.5 km
  • Fair Oaks Mall
    53 min drive - 57.0 km

Getting around

  • Washington Dulles Intl. Airport (IAD)
    51 min drive

Restaurants

  • The Ashby Inn & Restaurant
    7 min drive
  • Hunter's Head Tavern
    2 min walk
  • Three Fox Vineyards & Brewery
    14 min drive
  • Upperville Country Store
    3 min walk
  • Wolfe Tone's Irish Pub
    5 min drive

Frequently asked questions

Is Historic spacious home in the heart of Upperville, VA pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 50 lbs per pet.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Historic spacious home in the heart of Upperville, VA ?

Check-in begins at 3:00 PM.

What time is check-out at Historic spacious home in the heart of Upperville, VA ?

Check-out is at 11:00 AM.

Where is Historic spacious home in the heart of Upperville, VA located?

Situated in Upperville, this vacation home is 0.4 mi (0.6 km) from Upperville Park and within 6 mi (10 km) of Sky Meadows State Park and Paris Barns. RdV Vineyards and PEC Holding are also within 6 mi (10 km).

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Reviews

Historic spacious home in the heart of Upperville, VA Reviews

9.6

Exceptional

9.8

Cleanliness

10

Location
Rating 10 - Excellent. 6 out of 7 reviews
Rating 8 - Good. 0 out of 7 reviews
Rating 6 - Okay. 1 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful place

This place was beautiful, spacious and immaculate. It was a very relaxing stay. I would certainly recommend this place.
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

A wonderful house

We loved staying here, by far our favorite part was the gardens. We sat outside as much as we could and it made the whole setting so lovely. A well appointed kitchen and nice linens made our stay so comfortable. Our kids found soccer balls and things to play with. I can't recommend it enough for a big family group!
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful house

We had a great stay!
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was amazing! the host was super responsive and helpful! We would definitely stay here again!
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Old house charm, well equipped and away from the hustle and bustle of the big cities. More space than needed for our family of 5 during a week of DC and battlefield touring. Host added full-bloom orchids, sometimes multiple, in every one of at least 11 rooms!
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Nov 2024