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Historic spacious home in the heart of Upperville, VA

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Exterior
Exterior
Outdoor dining
Terrace/patio
Interior

Reviews

10 out of 10
Exceptional
4 bedrooms3+ bathroomsSleeps 10

Popular amenities

  • Kitchen
  • Washer
  • Pet friendly
  • Air conditioning
  • Outdoor Space
  • Parking available

Explore the area

View in a map
Upperville, VA
  • Place, Upperville Park
    ‪11 min walk‬
  • Place, Fair Oaks Mall
    ‪46 min drive‬
  • Place, Hollywood Casino at Charles Town Races
    ‪48 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 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.

Add dates for prices

Amenities

Kitchen
Washer
Pet friendly
Air conditioning
Outdoor Space
Parking available

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Exterior detail
Historic house in Upperville! Wineries, equestrian events, great location!
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10.0 out of 10, Exceptional, (31 reviews)
Historic house in Upperville! Wineries, equestrian events, great location!

House Rules

Check in after 2:00 PM
Minimum age to rent: 25
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

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 - 0.9 km
  • Fair Oaks Mall - 46 min drive - 78.7 km
  • Reston Town Center - 47 min drive - 62.2 km
  • Hollywood Casino at Charles Town Races - 48 min drive - 64.4 km
  • Harpers Ferry National Historical Park - 49 min drive - 60.7 km

Getting around

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

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

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 Apr 1, 2026, prices found for a 1-night stay for 2 adults at Historic spacious home in the heart of Upperville, VA on Jun 14, 2026 start from $551, 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).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 5 out of 5 reviews
Rating 8 - Good. 0 out of 5 reviews
Rating 6 - Okay. 0 out of 5 reviews
Rating 4 - Poor. 0 out of 5 reviews
Rating 2 - Terrible. 0 out of 5 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Karuna P.

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

Beautiful house

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

10/10 Excellent

Ann P.

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

10/10 Excellent

Vonda F.

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

10/10 Excellent

Somerset G.

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

10/10 Excellent

Jennifer H.

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

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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