Historic spacious home in the heart of Upperville, VA | House in Upperville

10.0 (5 Reviews) |   Pet Friendly   4 Bedrooms  3 Bathrooms  10 Guests
Upperville House | Historic spacious home in the heart of Upperville, VA

4 Bedroom House in Upperville

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."

Historic spacious home in the heart of Upperville, VA is located in Upperville. Historic spacious home in the heart of Upperville, VA provides accommodation, featuring Balcony/Terrace, Security/Safety, Barbecue/Outdoor Cooking, among other amenities. This House features Balcony/Terrace, Security/Safety, Barbecue/Outdoor Cooking, to make your stay a comfortable one.

Historic spacious home in the heart of Upperville, VA has 4 Bedrooms , 3 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Upperville has interesting places to visit. If you want to learn more about the House in Upperville, such as places to visit and things to do nearby, you can check below to learn more.

Show more
OneKey Logos

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY

Amenities

Air Conditioner
Parking
Pet Friendly
TV
Balcony/Terrace
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Heating
  • Air conditioning
Bathrooms
  • Toilet paper
  • Towels provided
  • Shampoo
  • Hair dryer
  • 3+ bathrooms
  • Bathtub or shower
  • Soap
Bedroom
  • Bed sheets provided
  • Sofa bed
  • 4 bedrooms
  • Fireplace
Kitchen
  • Microwave
  • Cookware/dishes/utensils
  • Spices
  • Toaster
  • Oven
  • Electric kettle
  • Dishwasher
  • Stovetop
  • Refrigerator
Laundry
  • Washing machine
  • Laundry facilities
Parking
  • Onsite parking
Pet Friendly
  • Pet friendly
  • Welcoming dogs only
  • 2 total (up to 50 lbs per pet)
Accessibility
  • Smoke-free property
Entertainment
  • Games
  • Smart TV
General
  • English
Guest Services
  • Children's games
  • Playground
  • Travel crib
  • Children's books
  • Children's dinnerware
  • Iron/ironing board
Internet
  • WiFi available
Outdoors
  • Barbecue grill
  • Garden
Security/Safety
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)

Policies

Check-in
Check-in time starts at 2:00 pm minimum check-in age: 25
Check-out
Check-out before 11:00 am
Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
2 total (up to 50 lbs per pet) pets allowed service animals are welcome, and are exempt from fees welcoming dogs only
Smoking Policy
Smoking is not permitted

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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

Reviews

Ann P.
Nov 7, 2025 11:20:45 AM
Review Score:   10
Summary: The house was amazing! the host was super responsive and helpful! We would definitely stay here again!
See All Reviews

FAQ's

Is this Upperville house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Upperville house have a swimming pool?

No, this Upperville house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Upperville house?

Best-rates for the Upperville house starts from $607 per night with includes Wellness Facilities, Laundry, Air Conditioner, Pet Friendly, Sports/Activities, Fireplace/Heating, Entertainment, Child Friendly, TV, Internet, Kitchen, Balcony/Terrace, Security/Safety, Barbecue/Outdoor Cooking, Parking, Bedding/Linens with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is Upperville house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Upperville house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Upperville house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Upperville house?

Based on the information reported by the owner or manager, the Upperville house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Upperville house?

Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Check House Availability
Nightly rates from:
USD607
You will be redirected to  
Hot Deal - It has been viewed 170 times today
Not the right fit? Check out our other properties in Upperville
Historical Paris Cabin on Farm with Fire Pit! From US $405
         

|
10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • View
Grand 9BR Provenance Manor Ideal for Gatherings From US $1,693
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
18th Century Stone Cottage minutes from historic Middleburg From US $394
         

10.0 (52 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Hunt Country cottage in Upperville! From US $191
         

10.0 (28 Reviews)
Cottage
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Nature Escape Pond Dock Fire Pit Trails From US $1,066
         

New
House
  • Air Conditioner
  • View
  • Security/Safety
Nature Escape - Pond, Dock, Fire Pit, Trails From US $914
         

Cozy Country Getaway in the Heart of Upperville From US $304
         

10.0 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Historic spacious home in the heart of Upperville, VA From US $607
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Historical Paris Cabin on Farm w/Fire Pit! From US $330
         

10.0 (5 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Guest House at Mt Independence From US $303
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Elegant Paris Manor w/Private Pool! From US $1,876
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Grand 9BR Provenance Manor Ideal for Weddings & Gatherings From US $1,797
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Welcome to the Ladybug Retreat! From US $221
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Historical cottage in the town of Paris From US $229
         

9.8 (52 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Nature Escape | Pond Dock Fire Pit Trails From US $735
         

8.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Quiet Virginia Wine Country Retreat From US $268
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Farm Suite at Valley View Farm From US $214
         

New
Apartment
  • Air Conditioner
  • Parking
  • TV