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Historic house in Upperville! Wineries, equestrian events, great location!

Photo gallery for Historic house in Upperville! Wineries, equestrian events, great location!

Exterior detail
Property grounds
Exterior
Entering on the side porch
Private kitchen

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
5 bedrooms3 bathroomsSleeps 11

Popular amenities

  • Washing machine
  • Dryer
  • Air-conditioning

Explore the area

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

Rooms & beds

5 bedrooms (sleeps 11)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Single Bed

Bedroom 5

1 Queen Bed and 2 Single Beds

3 bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Hair dryer

Bathroom 2

Soap · Towels provided · Bathtub or shower · Toilet · Hair dryer

Bathroom 3

Soap · Towels provided · Shower only

About this property

Historic house in Upperville! Wineries, equestrian events, great location!

The Stone house in Upperville, Virginia is a new listing, and a wonderful blend of old stone walls and exposed beams - and modern touches of comfort for today’s living. Perfect for family gatherings and exploring the surrounding countryside, the stone house offers the perfect location to explore wineries, equestrian events and local history!
Built in 1734 and the oldest in the area, the Stone House is said to have been a tavern for travelers (one can still sometimes hear the clop clop of 4-in hand coaches going by), as well as having changed hands multiple times as battlefield headquarters during the Civil War. A truly bi-partisan house! Historic markers across the road and ¼ mile up Trapp road designate the battle of Upperville – soldiers camped in the adjacent creek area near the remains of the Mill.
But it's not just about battles! For the horse enthusiast, the well known Upperville show grounds are within a mile of the Stone House, and home to the Spring and Fall Steeplechase races in addition to the horse shows; Great Meadow is 25 minutes away and has polo every weekend as well as the Gold Cup and varied field events. Rocket launch club anybody? Hiking at nearby Sky Meadow provides amazing views of the valley and the Appalachian trail is also within easy reach. River rafting in Harpers Ferry, and if you like working mills and tiny towns with great lunches and antiques, the village of Millwood is 20 minutes away. Pick your own veggies and fruit areas are plentiful in the area, as are wineries (two within 3 miles and dozens in the area).
So much to see and learn!
Restaurants in Upperville and nearby Middleburg are bustling, but if you prefer local farm to table, The Market at Bluewater Kitchen in the village will stock your fridge on your arrival day and deliver prepared meals if you prefer. Hunter's Head Tavern in the village also offers farm to table meals in a historic setting.
Churches are plentiful in Upperville - Trinity Church in the village was a gift to the Parish by Mr and Mrs Paul Mellon, and is beautiful and welcoming to all visitors. There are two Baptist churches, one in the village and Mt. Pisgah on nearby Delaplane road, and Upperville United Methodist Church. So many churches for a tiny village.
The Stone House is adjacent to The Mill House, listing #1312169.

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Amenities

Washing machine
Dryer
Air conditioning

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Porch leading to mill and pool
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  • Kitchen
  • Washing machine
  • Dryer
10.0 out of 10, Exceptional, (153 reviews)
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House Rules

Check in after 3:00 PM
Minimum age to rent: 30
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

No pets allowed
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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
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

About the area

Upperville

Upperville is home to this holiday home. Sky Meadows State Park and PEC Holding reflect the area's natural beauty and area attractions include Paris Barns and National Sporting Library & Museum. Museum of Hounds & Hunting North America and Northern Fauquier Community Park are also worth visiting.
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Map
Upperville, VA

What's nearby

  • Upperville Park - 2 min drive - 1.4 km
  • Jiffy Lube Live - 35 min drive - 54.9 km
  • Fair Oaks Mall - 45 min drive - 78.0 km
  • Hollywood Casino at Charles Town Races - 47 min drive - 63.7 km
  • Reston Town Center - 48 min drive - 62.9 km

Getting around

  • Washington Dulles International Airport (IAD) - 48 min drive

Restaurants

  • ‪Hunter's Head Tavern - ‬11 min walk
  • ‪The Ashby Inn & Restaurant - ‬6 min drive
  • ‪Three Fox Vineyards & Brewery - ‬13 min drive
  • ‪RdV Vineyards - ‬11 min drive
  • ‪Delaplane Cellars - ‬12 min drive

Frequently asked questions

Is Historic house in Upperville! Wineries, equestrian events, great location! pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Historic house in Upperville! Wineries, equestrian events, great location!?

As of 4 Mar, 2026, prices found for a 1-night stay for 2 adults at Historic house in Upperville! Wineries, equestrian events, great location! on 7 Jun, 2026 start from S$954, 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.

What time is check-in at Historic house in Upperville! Wineries, equestrian events, great location!?

Check-in begins at 3:00 PM.

What time is check-out at Historic house in Upperville! Wineries, equestrian events, great location!?

Checkout is at 11:00 AM.

Where is Historic house in Upperville! Wineries, equestrian events, great location! located?

Situated in Upperville, this holiday home is 0.9 mi (1.4 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).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 31 out of 31 reviews
Rating 8 - Good. 0 out of 31 reviews
Rating 6 - Okay. 0 out of 31 reviews
Rating 4 - Poor. 0 out of 31 reviews
Rating 2 - Terrible. 0 out of 31 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Monica T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house, fabulous location, wonderful gathering places, clean and comfortable! Would highly recommend!
Stayed 3 nights in Nov 2025

10/10 Excellent

Abigail M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home with lots to do in surrounding areas. Host was very responsive and communicative
Stayed 3 nights in Nov 2025

10/10 Excellent

Erin L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing house! We had a great stay. The house is fully stocked with everything you could possibly need.
Stayed 3 nights in Oct 2025

10/10 Excellent

Anela M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely property, great for a group getaway! Quiet, has everything you need.
Stayed 3 nights in Aug 2025

10/10 Excellent

Stacy L.

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

40th girls trip

had a great weekend stay
Stayed 2 nights in May 2025

10/10 Excellent

Jennifer V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
My childhood girlfriends and I were overdue for some quality time together and wanted to stay in a comfortable home with access to wineries, hiking and restaurants. We had a wonderful stay. The home was clean, comfortable and absolutely charming. The kitchen had everything we needed and communication and recommendations from the owner, Constance, were plentiful. We were close to many attractions and had the perfect weekend. I would highly recommend her home for a calm and cozy visit.
Stayed 3 nights in Oct 2025

10/10 Excellent

william F.

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

Excellent property

Our host was amazing and gave us a history tour. I would highly recommend this historic property.
Stayed 5 nights in May 2025

10/10 Excellent

Mark G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful charming house with plenty of space to spread out and a great location! The host was a pleasure to work with and always available.
Stayed 5 nights in Jun 2025

10/10 Excellent

Shay B.

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

Loved out stay

Would definitely stay again
Stayed 2 nights in Aug 2023

10/10 Excellent

Christine F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Spacious, clean and a very helpful and responsive host! I have already rebooked for next year. Five stars all around!
Stayed 7 nights in Jun 2025

10/10 Excellent

Mary Jane G.

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

A comfortable week with large family

Our family of 16 stayed in the Stone House and its sister property, the Mill House. Houses are so attractivly furnished. I wish the owner would do a consult at my place. There is so much to do in the area: hiking, fruit picking, strolling around Middleburg. We have stayed here before and always enjoy it very much.
Stayed 7 nights in Jul 2025

10/10 Excellent

Melanie G.

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

Peaceful getaway in wine country

Beautiful historic house, well kept, on tranquil grounds! Close drive to lots of wineries. Check in & Check out process couldn’t have been easier. Host replied to all questions in a very timely manner. Would recommend!
Stayed 2 nights in Apr 2025

10/10 Excellent

Hensh B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house was perfect for our family wedding weekend in Middleburg. We could not be more pleased with all accommodations including communicating with Constance the owner. She even purchased a handicap shower chair with handles for my elderly parents. That spoke volumes as to what kind of home owner she is. Thank you again!!!
Stayed 2 nights in Oct 2025

10/10 Excellent

Thomas H.

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

Historic charm and convenience

We stayed with friends (6 adults) and had an amazing time! The house was still decorated for the holidays which added a wonderful, warm touch for our visit. They've maintained all the charm of a historic house with modern amenities for a perfect stay. Absolutely perfect spot for get together. We'll be returning soon!
Stayed 2 nights in Dec 2024

10/10 Excellent

Rafael A.

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

Historic charm

A charming 18th century house with modern appointments that made for a pleasant and comfortable stay. The property owner showed great attention to detail, and she was very attentive. It was a delightdul stay!
Stayed 2 nights in Aug 2024

10/10 Excellent

Catherine Y.

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

The perfect girls weekend!

We absolutely loved our stay! We had 10 girls in our late 20s and there was plenty of room for us to all hang out in the common spaces. We enjoyed day at the local vineyards but honestly spent most of our time cozied up in the lovely living room. The house is beautifully maintained and the host is so kind and gracious. Cannot recommend enough!
Stayed 3 nights in Feb 2025

10/10 Excellent

Beth H.

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

Beautiful Home

We had a wonderful stay at this beautiful home. We could not have asked for better accommodations. The homeowner was so helpful in offering suggestions of things to do and places to eat. This was a 5 star weekend.
Stayed 2 nights in May 2024

10/10 Excellent

Maureen R.

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

Wonderful stay

Seven high school girlfriends celebrating our 60th year spent a long weekend at the Stone House and it did not disappoint. Plenty of space to spread out and relax. The location was ideal for visiting Middleburg and local hiking trails. The host was very welcoming and quick to respond to question. Would highly recommend this property.
Stayed 3 nights in Apr 2024

10/10 Excellent

Kathy H.

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

Historical clean home in nice area!

House was well equipped and clean. It was spacious for our family of 11. We had great conversation around the dining room table. Thank you!
Stayed 3 nights in Apr 2024

10/10 Excellent

Genna C.

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

Beautiful Historic Home for Corporate Retreat

We were able to move from room to room and then to the beautiful outdoors as we conducted a leadership retreat for our company. Constance was amazing and made us feel like friends. She recommended trivia night at a local tavern and called ahead so we received a warm welcome. It was a great place!!!!
Stayed 3 nights in Apr 2024

10/10 Excellent

Naomi P.

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

Lovely Historic Home

Our family of nine enjoyed a weekend getaway at the beautiful Stone House in late October. The house is just as pictured and had everything we needed. The outdoor space is lovely as well. Constance was so kind and helpful with local recommendations before our visit and responded very quickly when we had a small issue during our stay. We would definitely stay at the Stone House again!
Stayed 2 nights in Oct 2023

10/10 Excellent

Judy L.

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

Bluemont Bridal Party

This home was everything my daughter imagined for her big day preparations. It is very clean and spacious with close proximity to the Grooms house in the same lane. The host, Constance was superb!! Thank you for everything
Stayed 3 nights in Oct 2024

10/10 Excellent

ac P.

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

Horse country getaway

Just the right mix of historic and modern. We thoroughly enjoyed our stay here and look forward to coming back next year. Comfortably appointed for a large group. Ample communal relaxing space on the first floor as well as outdoor spaces. The host was very responsive and even went the extra mile to return an item that we left behind. Highly recommend!
Stayed 3 nights in Oct 2023

10/10 Excellent

Mary Jane G.

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

Another fun family trip

We have stayed in another house with the same owner before. She has lovely taste, and the house is comfortable and well-stocked. The kitchen is great to work in. Every description is entirely accurate. I just wish she'd come tweak my house and make it better!
Stayed 6 nights in Jul 2024

10/10 Excellent

Glenna P.

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

Historic and Cozy

Friends and I stayed here during the Middleburg Classic horse show. What a charming historic classic Upperville home. The house is as advertised, an older home with a few quirks but overall it was delightful. Every room has a gorgeous stone fireplace and a comfortable bed. The kitchen is attractive and functional and it has a lovely back deck. Constance was a very attentive and helpful host. We hope to stay here again!
Stayed 5 nights in Sep 2023

About the host

Hosted by Constance Chatfield-Taylor

Host profile image
I'm a Virginian, through and through. History has always intrigued me, and restoring houses has been an interest for many years. The gathering of friends and family is very important, and sharing the capabilities for doing that for others is something that I enjoy.

Why they chose this property

The churches, the charm of the village, the people. Proximity to hiking and horses and wineries!

What makes this property unique

History, stone work, exposed beams, large airy rooms that are full of charm at the same time.

Languages:

English

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