Entire home

Historic spacious home in the heart of Upperville, VA

Holiday home in Upperville with kitchen and fireplace

Dining - Historic spacious home in the heart of Upperville, VA (Upperville)

Property grounds - Historic spacious home in the heart of Upperville, VA (Upperville)

4 bedrooms, iron/ironing board, travel cot, WiFi - Historic spacious home in the heart of Upperville, VA (Upperville)

Smart TV, fireplace - Historic spacious home in the heart of Upperville, VA (Upperville)

Experience the charm of Upperville at The Upperville Academy, a beautifully restored historic home with 4000 SF of natural light and modern amenities. Enjoy gatherings with family and friends in the exquisite 2.5-acre garden or relax in this dog-friendly haven.

Exceptional

Entire home

4 bedrooms4 bathroomsSleeps 10

Popular amenities

Kitchen
Washing machine
Pet-friendly
Air-conditioning
Outdoor space
Parking available

Add dates for prices

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."

Property amenities

Internet

Available in the house: WiFi

Parking and transport

Parking on site

Kitchen

Blender
Coffee grinder
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Hob
Microwave
Oven
Refrigerator
Spices
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
Up to 23 kg per pet

Suitability/Accessibility

Smoke-free property

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

Similar properties

Spa pool
Kitchen
Free Wi-Fi
Air-conditioning

includes taxes & fees

8 Jan - 9 Jan 2026

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 allowed

Service animals are welcome, and are exempt from fees

Welcoming dogs only

2 total (up to 23 kg per pet)

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

On-site parties or group events are strictly prohibited

Host has indicated that there is a carbon monoxide detector on the property

Host has indicated that 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

About the area

Upperville, VA

What's nearby

Upperville Park - 11 min walk - 0.9 km
Dulles Expo Conference Center - 40 min drive - 50.4 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

Getting around

Washington Dulles International 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 23 kg per pet.

How much is parking at Historic spacious home in the heart of Upperville, VA ?

On-site 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 ?

Checkout is at 11:00 AM.

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

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

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Historic spacious home in the heart of Upperville, VA Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.

More information

10

Cleanliness

10

Location

10/10 Excellent

Karuna P.

1 Aug 2025

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

Beautiful house

We had a great stay!

Stayed 2 nights in Jul 2025

10/10 Excellent

Vonda F.

29 May 2024

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

10/10 Excellent

Somerset G.

29 July 2024

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