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Historic spacious home in the heart of Upperville, VA

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

Reviews

9.6 out of 10
Exceptional

Entire home

4 bedrooms4 bathroomsSleeps 104000 sq ft

Popular amenities

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

Explore the area

View in a map
Upperville, VA
  • Place, Upperville Park
    ‪11 min walk‬
  • Place, Hollywood Casino at Charles Town Races
    ‪49 min drive‬
  • Place, Fair Oaks Mall
    ‪53 min drive‬
  • Airport, Washington, DC (IAD-Washington Dulles Intl.)
    ‪47 min drive‬

Room options

About the neighborhood

Upperville

Located within a leisurely stroll of Upperville Park, this vacation home is within a 10-minute drive of Paris Barns. The vacation home includes a kitchen, a fireplace, and a sofa bed.
View more Vacation Homes in UppervilleOpens in a new window

What's nearby

  • Upperville Park - 11 min walk - 0.6 miles
  • Jiffy Lube Live - 43 min drive - 37.7 miles
  • Hollywood Casino at Charles Town Races - 49 min drive - 40.7 miles
  • Harpers Ferry National Historical Park - 50 min drive - 42.9 miles
  • Fair Oaks Mall - 53 min drive - 35.4 miles

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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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."
The vacation home is air-conditioned and features a kitchen and 3.5 bathrooms, and there's space to spread out with 4 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a fireplace, and a sofa bed.

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  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
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Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Bedrooms

  • 4 bedrooms
  • Bed sheets provided
  • Sofa bed

Bathroom

  • 3.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Fireplace

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total (up to 50 lbs per pet)

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • Garden
  • Unit size: 4,000 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Strip any used beds, gather used towels, and store extra beds
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.

Pets

  • This property welcomes pets
  • Dogs only
  • 2 total (50 lbs is the maximum weight per pet)
  • Service animals exempt from fees

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
  • Check-in: 3:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector and a smoke detector.

Frequently asked questions

What can I see within easy reach of this vacation home?

This vacation home is located in Upperville within a short 8-minute walk of Upperville Park. You'll also find Sky Meadows State Park and Paris Barns within a short drive.

Is there parking available at Historic spacious home in the heart of Upperville, VA ?

No, this vacation home doesn't offer parking.

Is this vacation home next to a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

What amenities will couples enjoy at Historic spacious home in the heart of Upperville, VA ?

Amenities that appeal to couples at this vacation home include a fireplace, a smart TV, and a kitchen.

Are there hot tubs at Historic spacious home in the heart of Upperville, VA ?

No, there isn't a spa tub at this vacation home.

Does this vacation home provide breakfast?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay free of charge?

Although dogs can't stay for free, they are welcome at this vacation home.

Are there connecting rooms at Historic spacious home in the heart of Upperville, VA ?

No, this vacation home doesn't feature connecting guestrooms.

How close is the airport from this vacation home?

The closest major airport to this vacation home is Washington Dulles Intl. Airport (IAD), which is about 23.3 mi away. Another top airport is Manassas, VA (MNZ-Manassas Regional), which is around 27 mi away.

Are there rooms with balconies at Historic spacious home in the heart of Upperville, VA ?

No, you won't find house with balconies at Historic spacious home in the heart of Upperville, VA .

Historic spacious home in the heart of Upperville, VA Reviews

Reviews

9.6

Exceptional

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

9.8/10

Cleanliness

Reviews

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

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
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

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
Stayed 2 nights in Nov 2024

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