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Historic spacious home in the heart of Upperville, VA

Upperville vacation home with kitchen

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

Property grounds
Smart TV, fireplace
4 bedrooms, iron/ironing board, travel crib, WiFi
Exterior
Fridge, microwave, oven, stovetop

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms4 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, Hollywood Casino at Charles Town Races
    ‪49 min drive‬
  • Place, Harpers Ferry National Historical Park
    ‪50 min drive‬
  • Airport, Washington, DC (IAD-Washington Dulles Intl.)
    ‪47 min drive‬

Room options

About the area

Upperville

In Upperville .A stay at this vacation home places you within half a mile (1 km) of Upperville Park and 6 miles (10 km) of Sky Meadows State Park. Paris Barns and RdV Vineyards are also within 6 miles (10 km).
View more Vacation homes in UppervilleOpens in a new window

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 - 65.5 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

  • ‪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

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."

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Property amenities

Internet

  • Available in the house: WiFi

Parking and transportation

  • Parking on site

Kitchen

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

Bedrooms

  • 4 bedrooms
  • Bedsheets 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

Policies

Check-in

Check-in time starts at 2:00 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

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 2 (weight limit: 50 lbs per pet)
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in each accommodation.

Frequently asked questions

How close is Historic spacious home in the heart of Upperville, VA to the airport?

This vacation home is 35.8 mi (51-min drive) away from the Washington Dulles Intl. Airport (IAD) airport, the closest popular airport to the property.

Does Historic spacious home in the heart of Upperville, VA have an airport shuttle?

Airport shuttle services are not available at this vacation home.

Does Historic spacious home in the heart of Upperville, VA offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Historic spacious home in the heart of Upperville, VA ?

No, there is no casino at this vacation home.

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

Check-in begins at 2:00 PM.

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

Free parking is not available at this vacation home.

Does Historic spacious home in the heart of Upperville, VA have a pool?

This vacation home does not have a pool.

Does Historic spacious home in the heart of Upperville, VA have a spa?

There are no spa services available at this vacation home.

How close is Historic spacious home in the heart of Upperville, VA to downtown Upperville?

This vacation home is 0.4 mi away from Upperville.

Historic spacious home in the heart of Upperville, VA Reviews

Reviews

10

Exceptional

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

10/10

Cleanliness

Reviews

10/10 Excellent

Joel V.

Liked: Cleanliness
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

10/10 Excellent

Ann P.

Liked: Cleanliness
The house was amazing! the host was super responsive and helpful! We would definitely stay here again!
Stayed 3 nights in Oct 2025

10/10 Excellent

Karuna P.

Liked: Cleanliness

Beautiful house

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

10/10 Excellent

Jennifer H.

Liked: Cleanliness
Stayed 2 nights in Nov 2024

10/10 Excellent

Somerset G.

Liked: Cleanliness

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

10/10 Excellent

Vonda F.

Liked: Cleanliness

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