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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.
A bedroom with a bed, a desk, a chair, a television, and a window with curtains.
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.
A porch with a blue carpet, white railing, and blue rocking chairs.
A grand piano in a spacious living area with a wooden floor and a white staircase.

Reviews

10 out of 10
Exceptional

Highlights

  • Games
    A rare find - enjoy a variety of games available on-site.
Sleeps 10•4 bedrooms•6 beds

Popular amenities

  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washer
  • Air conditioning
  • Barbecue grill

Explore the area

View in a map
Upperville, VA
  • Place, Upperville Park
    ‪11 min walk‬
  • Place, Jiffy Lube Live
    ‪43 min drive‬
  • Place, Hollywood Casino at Charles Town Races
    ‪49 min drive‬
  • Airport, Washington, DC (IAD-Washington Dulles Intl.)
    ‪47 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 Twin 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."
Our prices include all fees. No hidden fees.

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House Rules

Check in after 2:00 PM
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total)
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 3752987
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property

About the neighborhood

Upperville

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.
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Map
Upperville, VA

What's nearby

  • Upperville Park - 11 min walk - 1.0 km
  • Jiffy Lube Live - 43 min drive - 61.0 km
  • Hollywood Casino at Charles Town Races - 49 min drive - 65.8 km
  • Harpers Ferry National Historical Park - 50 min drive - 69.0 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
  • ‪RdV Vineyards - ‬11 min drive
  • ‪Delaplane Cellars - ‬14 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 does it cost to stay at Historic spacious home in the heart of Upperville, VA ?

As of Aug 20, 2026, prices found for a 1-night stay for 2 adults at Historic spacious home in the heart of Upperville, VA on Aug 30, 2026 start from $880, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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 2:00 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).

About the host

Hosted by Jennifer Clinton

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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