A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

Holiday Homes in Upperville

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Upperville holiday homes

A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

1. Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
Front Royal
9.0 out of 10, Wonderful, (32 reviews)
"The house itself was clean, the beds are comfortable, and it is in a nice, quiet, and private location. The property manager was very pleasant and responsed to any questions or concerns quickly. "
United States
Elissa S.
The price is NZ$506
includes taxes & fees
7 Sept - 8 Sept
Mountain home w/ hot tub & sunroom
A two-story house with a porch, surrounded by trees and grass.

2. 1910 Farmhouse on 6 Acres • VA Wine Country

1910 Farmhouse on 6 Acres • VA Wine Country
Marshall
9.6 out of 10, Exceptional, (5 reviews)
"We love this house. It was super quiet and cozy. The kitchen is the best stocked Vrbo kitchen we have ever encountered. If there is a drawback, I would say that it is the antique/original doorknobs. They do need to be repaired or replaced for ease of use. But on the other hand, no biggie and kind of add to the charm. We thoroughly enjoyed our stay!"
United States
Mark H.
The price is NZ$648
includes taxes & fees
26 Aug - 27 Aug
1910 Farmhouse on 6 Acres • VA Wine Country
A spacious kitchen with modern appliances, a dining area with a large table and chairs, and a view through a glass door.

3. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful house in a beautiful location. The house was very good for relaxing and hanging out with old friends with its open concept. Bedrooms were on the small side but functional as were the bathrooms. The kitchen was very nice and a nice coffee bar was provided with a Nespresso machine and milk frother."
United States
Mark W.
The price is NZ$857
includes taxes & fees
1 Sept - 2 Sept
Spacious Modern Home on Middleburg Horse Farm

4. Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
10.0 out of 10, Exceptional, (1 review)
"Amazingly comfortable place to call home for a few days with plenty of room for activities if you have to stay in! Bedrooms were lovely as were the bathrooms. Updated and very clean!!!! Host was extremely responsive and very easy to work with!! Bonus to bring our pup with us for the stay."
United States
K O.
The price is NZ$531
includes taxes & fees
31 Aug - 1 Sept
Bluemont home just minutes to wineries, breweries, hiking and more!

5. Historic Farmhouse, Fully Renovated in Fall 2023

Historic Farmhouse, Fully Renovated in Fall 2023
Loudoun County
9.8 out of 10, Exceptional, (10 reviews)
The price is NZ$795
includes taxes & fees
21 Sept - 22 Sept
Historic Farmhouse, Fully Renovated in Fall 2023
A wooden deck with two Adirondack chairs and a small table, two wine glasses on the table, surrounded by lush green trees.

6. 4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Harpers Ferry
9.6 out of 10, Exceptional, (9 reviews)
"House was beautiful and fully equipped for our stay. The host was very communicative and we really enjoyed our time here. If in the area again would definitely stay here. "
United States
Maeve K.
The price is NZ$749
includes taxes & fees
1 Sept - 2 Sept
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

7. Mountain Views w/Hot Tub, 95” TV & Trail Access

Mountain Views w/Hot Tub, 95” TV & Trail Access
Shenandoah Farms
10.0 out of 10, Exceptional, (1 review)
"We were looking for a comfortable home base to explore Front Royal and Skyline Plaza, and this was perfect! A modernized home with enough amenities that we were tempted every day to just stay “home!” The kids loved the reading nook and cozy sitting areas, and the fire pit and clean, working hot tub were big pluses as well. Kitchen was roomy, with great appliances and plenty of counter space. Beds were comfortable. Bathrooms were nice and modern. Lots of closet space, too. When we left, the kids...
United States
Joshua J.
The price is NZ$601
includes taxes & fees
24 Sept - 25 Sept
Mountain Views w/Hot Tub, 95” TV & Trail Access
A deck with outdoor seating and a lake view.

8. Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
9.8 out of 10, Exceptional, (9 reviews)
"Had a wonderful stay here. Shaun was an excellent host with easy communication. Peaceful location with a lake! Convenient to Harper’s Ferry. "
United States
Liz P.
The price is NZ$402
includes taxes & fees
13 Sept - 14 Sept
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

9. 4BR Golf Retreat | 3 Courses | Pool Table

4BR Golf Retreat | 3 Courses | Pool Table
Front Royal
10.0 out of 10, Exceptional, (1 review)
"Home was clean and looked like it had recently been remodeled/updated. The host was very responsive and when the oven wasn't working properly, they went to Lowes and purchased a new one immediately! Made our short trip much easier not having to eat out or find a last minute option for our kids/babysitter on Friday evening. We were only in town from Thursday-Sunday, and it was perfect for the 5 of us. The pool table was a fun addition for the kids. The only minor complaint I have is that I wish I...
United States
Crystal H.
The price is NZ$736
includes taxes & fees
26 Aug - 27 Aug
4BR Golf Retreat | 3 Courses | Pool Table

10. Cozy Bear Chase Cottage

Cozy Bear Chase Cottage
Mount Weather
10.0 out of 10, Exceptional, (45 reviews)
"Bear Chase is the ideal getaway from Alexandria, make the drive and stay the weekend or a week. Wonderful beer and other beverages, terrific food and entertainment. Amazing staff and the views and grounds are spectacular."
United States
Scott F.
The price is NZ$1,402
includes taxes & fees
18 Sept - 19 Sept
Cozy Bear Chase Cottage

11. Entire home in Apple Mountain Lake, Virginia,

Entire home in Apple Mountain Lake, Virginia,
Apple Mountain Lake
The price is NZ$574
includes taxes & fees
26 Aug - 27 Aug
Entire home in Apple Mountain Lake, Virginia,
A wooden deck with white railings and a covered porch area.

12. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (37 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is NZ$364
includes taxes & fees
7 Sept - 8 Sept
Mountain View Bungalow in Front Royal
A hot tub under a wooden pergola with a view of autumn trees.

13. Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.6 out of 10, Exceptional, (15 reviews)
"We had a great stay "
United States
Lauren O.
The price is NZ$678
includes taxes & fees
26 Aug - 27 Aug
Huckleberry Hills | Hot Tub & Fire Pit & Dogs
A spacious dining area with a wooden table and chairs, large windows with a view of trees, and a stone wall in the background.

14. Stone Cabin on Valley View: Fire Pit + Hot Tub

Stone Cabin on Valley View: Fire Pit + Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful scenery! Beautiful home! Wonderful hosts!"
United States
Brian S.
The price is NZ$727
includes taxes & fees
8 Sept - 9 Sept
Stone Cabin on Valley View: Fire Pit + Hot Tub
A spacious living room with a green sofa set, a coffee table, and a fireplace. There is a kitchen in the background with a large window overlooking a deck.

15. Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (9 reviews)
"Welcoming host, great place!"
United States
Amanda M.
The price is NZ$557
includes taxes & fees
31 Aug - 1 Sept
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
A cozy dining area with a table and chairs, a view of a balcony with a railing, and a warm interior with wooden walls.

16. Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge

Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge
Shannondale
10.0 out of 10, Exceptional, (4 reviews)
Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge
A garden with a wooden swing set and a circular seating area.

17. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (49 reviews)
"What an absolutely lovely and peaceful place to stay! We had a wonderful visit. "
United States
Stephanie T.
The price is NZ$511
includes taxes & fees
27 Aug - 28 Aug
Newly renovated Farm cottage with Mountain views
A covered porch with a table and chairs, a number 64 on the wall, and a small garden area.

18. Farmhouse Retreat Sleeps 6, Yard for Tents, Near River + C&O Canal

Farmhouse Retreat Sleeps 6, Yard for Tents, Near River + C&O Canal
Harpers Ferry
7.2 out of 10, Good, (17 reviews)
"We had a great stay. Good location, close to Leesburg, Frederick, and Harper's Ferry center.The house was as described."
United States
Gwenaelle M.
The price is NZ$519
includes taxes & fees
31 Aug - 1 Sept
Farmhouse Retreat Sleeps 6, Yard for Tents, Near River + C&O Canal
A modern kitchen with a central island, stainless steel appliances, and a dining area with a view.

19. New 4br Townhome Near Harpers Ferry 4 Bedroom Townhouse

New 4br Townhome Near Harpers Ferry 4 Bedroom Townhouse
3.0 star property
Charles Town
The price is NZ$716
includes taxes & fees
31 Aug - 1 Sept
New 4br Townhome Near Harpers Ferry 4 Bedroom Townhouse
A modern kitchen with stainless steel appliances, a wooden countertop, and a large sliding glass door leading to a backyard.

20. Bend of Brothers’ | Riverfront Cottage Shenandoah

Bend of Brothers’ | Riverfront Cottage Shenandoah
Front Royal
8.0 out of 10, Very good, (1 review)
"This is a new place and owners have done great work . Excellent value for the money ."
United States
Dave B.
The price is NZ$619
includes taxes & fees
26 Aug - 27 Aug
Bend of Brothers’ | Riverfront Cottage Shenandoah
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Upperville Hotel Reviews

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"Staff great"
joyce 1-night trip
Posted 1 hour ago
Holiday Inn Winchester Se-Historic Gateway by IHG

Find out more about Upperville

Upperville Holiday Homes information

Number of reviews
241
Accommodation
241 Holiday Homes
Lowest Price
NZ$364
Highest Price
NZ$1,402