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Upperville Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Upperville vacation rentals

An aerial view of a rural property with a large barn, a farmhouse, and fenced fields.

1. "The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Markham
9.6 out of 10, Exceptional, (5 reviews)
"Such a lovely stay. The property was peaceful and relaxing, and the night sky was absolutely beautiful. We loved our time here and would happily return. Great communication (and snacks) too :)"
United States
Melissa B.
The price is AED 687
AED 1,072 total
includes taxes & fees
15 Nov - 16 Nov
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
A fenced grassy field with a clear sky and distant hills.

2. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.4 out of 10, Exceptional, (14 reviews)
"Beautiful, peaceful property. We originally lived in the area and were coming back to close out our business in town. The amenities in the home were great and everything was super clean. You definitely get the Northern Virginia rural experience here. Great location and hosts were amazing! Would stay here again!"
United States
Christina C.
The price is AED 551
AED 1,018 total
includes taxes & fees
26 Nov - 27 Nov
Lunar Loft, with mountain views
A wooden bridge leading to a house surrounded by lush greenery and purple flowers.

3. Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Bluemont
9.8 out of 10, Exceptional, (15 reviews)
"Nice owner, great place"
United States
Leslie C.
The price is AED 533
AED 1,223 total
includes taxes & fees
1 Dec - 2 Dec
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
A stone house with a chimney, surrounded by a well-maintained lawn and trees.

4. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (68 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
The price is AED 1,065
AED 1,442 total
includes taxes & fees
15 Nov - 16 Nov
18th Century Stone Cottage minutes from historic Middleburg
A cabin with a deck, a covered outdoor area, and a gravel path leading to the entrance.

5. Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
10.0 out of 10, Exceptional, (3 reviews)
"Really wonderful cabin. Everything was very clean and the house was super cute. Amenities were great. Would stay here again!!"
United States
Andrew G.
The price is AED 617
AED 1,608 total
includes taxes & fees
15 Nov - 16 Nov
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
A two-story house with a balcony, surrounded by trees and snow.

6. Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
9.4 out of 10, Exceptional, (11 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
The price is AED 533
AED 993 total
includes taxes & fees
30 Nov - 1 Dec
Cozy A frame cabin in quaint Front Royal. Dog friendly
A spacious living room with a fireplace, a dining area with a bench, and a large sliding glass door leading to an outdoor patio.

7. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.6 out of 10, Exceptional, (9 reviews)
"Great little hideout! We loved this little place, accurately described and the communication was superb!"
United States
P H.
The price is AED 514
AED 1,361 total
includes taxes & fees
16 Nov - 17 Nov
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
A two-story house with a porch, surrounded by trees and grass.

8. 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)
"If we managed to do everything, sing, dance, play, we loved the comfortable place for us"
United States
Erick U.
The price is AED 602
AED 1,323 total
includes taxes & fees
1 Dec - 2 Dec
1910 Farmhouse on 6 Acres • VA Wine Country
A hotel room with a bed, a dining table with chairs, a small table with a vase of flowers, and a storage unit with shelves.

9. Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Middleburg
9.6 out of 10, Exceptional, (29 reviews)
"The accomodations were clean and comfortable for our 1 night stay. "
United States
Claudia G.
The price is AED 551
AED 951 total
includes taxes & fees
22 Nov - 23 Nov
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
A cozy cabin interior with a wooden interior, a kitchen with a refrigerator, a dining area with a sofa, and a flat-screen TV mounted on the wall.

10. Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries

Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries
Front Royal
10.0 out of 10, Exceptional, (2 reviews)
"What a find!! Was looking for a place to relax and enjoy my wife’s birthday after taking in a local winery. Foxhole was a great cabin, convenient to home, very modern, w/lots of amenities. We’ll be back."
United States
Steven D.
The price is AED 826
AED 1,535 total
includes taxes & fees
22 Nov - 23 Nov
Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries
Local wineries, breweries, and small-town charm in Front Royal

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

Mountain Views w/Hot Tub, 95” TV & Trail Access
Shenandoah Farms
9.0 out of 10, Wonderful, (2 reviews)
"Just as described."
United States
Matt F.
The price is AED 839
AED 1,634 total
includes taxes & fees
16 Nov - 17 Nov
Mountain Views w/Hot Tub, 95” TV & Trail Access
A kitchen with a large island, wooden cabinets, a microwave, a coffee maker, and a window above the sink.

12. super cosy cottage with high speed internet!

super cosy cottage with high speed internet!
Middleburg
9.6 out of 10, Exceptional, (19 reviews)
"The area was surrounded by horses, Horse farms all around, which was lovely. Very quite and peaceful. Enjoyed my time there."
United States
Lynette
The price is AED 613
AED 1,097 total
includes taxes & fees
1 Dec - 2 Dec
super cosy cottage with high speed internet!
A covered outdoor deck with a fire pit, seating, and a view of the landscape.

13. Mountain Cabin Retreat | Hot Tub & Foosball |

Mountain Cabin Retreat | Hot Tub & Foosball |
Front Royal
9.0 out of 10, Wonderful, (12 reviews)
"Amazing house in an amazing place. The deck, view and sunsets are great stress reducers. Hope to visit again!"
United States
Christine T.
The price is AED 993
AED 2,045 total
includes taxes & fees
22 Nov - 23 Nov
Mountain Cabin Retreat | Hot Tub & Foosball |
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

14. Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (47 reviews)
"Nice cabin for couples. The bed was comfy and had all basic necessities for making meals. We will definitely stay again."
United States
Carla M.
The price is AED 771
AED 895 total
includes taxes & fees
15 Nov - 16 Nov
Blue Mountain Cabin, secluded, perfect for couples, near main road
A wooden deck with a hot tub, steps, and a view of a forest.

15. The Foxwood Cabin | Hot Tub, Screened Porch, Grill

The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Front Royal
10.0 out of 10, Exceptional, (7 reviews)
"Excellent stay. Very quiet and private. The property was very clean, had all of the amenities needed. Very comfortable and homey. The only thing you need to be aware of is that the USPS does not deliver to the address, Amazon will have the post office hold it in Front Royal."
United States
Roland C.
The price is AED 793
AED 1,803 total
includes taxes & fees
23 Nov - 24 Nov
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
A spacious kitchen with modern appliances, a dining area with a large table and chairs, and a view through a glass door.

16. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (23 reviews)
"Perfect for a mother and daughter get away. Peaceful and quiet. Short distance to Middleburg. Looking forward to staying here again. Already planning another trip with the whole family at Thanksgiving!"
United States
Denise B.
The price is AED 1,157
AED 2,098 total
includes taxes & fees
15 Nov - 16 Nov
Spacious Modern Home on Middleburg Horse Farm
A wooden deck with outdoor furniture and a fire pit, surrounded by trees and a railing.

17. Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive

Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive
Front Royal
9.4 out of 10, Exceptional, (3 reviews)
"All around great experience and beautiful spot!"
United States
casey p.
The price is AED 639
AED 1,467 total
includes taxes & fees
22 Nov - 23 Nov
Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive
A hot tub with a view of a forest and a sunset.

18. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.6 out of 10, Exceptional, (14 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
The price is AED 450
AED 1,197 total
includes taxes & fees
18 Nov - 19 Nov
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A wooden cabin with a porch, surrounded by trees and a gravel path.

19. The Grape Escape: Sip, Relax & Unwind in a Virginia Wine Country A-Frame

The Grape Escape: Sip, Relax & Unwind in a Virginia Wine Country A-Frame
Linden
10.0 out of 10, Exceptional, (32 reviews)
"This property was great for a weekend of relaxation!"
United States
Steven B.
The price is AED 705
AED 1,284 total
includes taxes & fees
1 Dec - 2 Dec
The Grape Escape: Sip, Relax & Unwind in a Virginia Wine Country A-Frame
A two-story house with a balcony, a hot tub, and a circular wooden structure.

20. Luxury Mountain Retreat w/ Valley Views, Hot Tub

Luxury Mountain Retreat w/ Valley Views, Hot Tub
Front Royal
9.4 out of 10, Exceptional, (3 reviews)
"Gorgeous views!!"
United States
Charlie R.
The price is AED 1,264
AED 2,368 total
includes taxes & fees
10 Dec - 11 Dec
Luxury Mountain Retreat w/ Valley Views, Hot Tub
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

Hotel Burg

Hotel Burg

10/10 Excellent
"Excellent food and service!!"
Alexandra 1-night trip
Posted 6 hours ago
Hotel Burg

Frequently asked questions

Can I find a vacation rental in Upperville?

Yes, we offer vacation rentals close to well known attractions in Upperville, or you can go with a more secluded option if you're looking for relaxation. Upperville is known for its restaurants.

What are some of the best vacation home rentals that Upperville has to offer?

Mountain View Bungalow in Front Royal: This vacation home rental outside of Upperville offers a garden, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Upperville?

Choose from 7 Expedia vacation rentals in Upperville for a memorable vacation.

What can I see and do in Upperville?

While exploring the area, visit family-friendly sights like Great Country Farms, or get outside and enjoy nature at Upperville Park. Sky Meadows State Park and Delaplane Cellars are a couple of places you'll find in the larger area.

What are vacation rentals like in Upperville?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Upperville. Vacation rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.