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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 holiday rentals

A balcony with a table, two wine glasses, and a view of a fenced area with a truck and a building in the background.

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 £222
includes taxes & fees
12 Nov - 13 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 £186
includes taxes & fees
17 Nov - 18 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 £249
includes taxes & fees
9 Dec - 10 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 £298
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 £331
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 £204
includes taxes & fees
12 Nov - 13 Nov
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 £280
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 £271
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 £196
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 £275
includes taxes & fees
16 Nov - 17 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 £336
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 £221
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 £326
includes taxes & fees
1 Dec - 2 Dec
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 £186
includes taxes & fees
10 Dec - 11 Dec
Blue Mountain Cabin, secluded, perfect for couples, near main road
A wooden deck with a grill, chairs, and a table.

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 £338
includes taxes & fees
16 Nov - 17 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 £425
includes taxes & fees
12 Nov - 13 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 £293
includes taxes & fees
12 Nov - 13 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 £242
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 £226
includes taxes & fees
12 Nov - 13 Nov
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 £382
includes taxes & fees
1 Dec - 2 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

A large, two-story house with a central entrance, multiple chimneys, and a well-maintained lawn with a pathway leading to the entrance.
Salamander Middleburg

Salamander Middleburg

Salamander Middleburg
Middleburg

8/10 Good

Great rooms but other facilities fall short. For this sort of money, I'd expect more.
United Kingdom
helen
Reviewed October 11, 2016
Salamander Middleburg

Find out more about Upperville

Everything you need to know about Upperville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upperville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upperville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Upperville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upperville. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upperville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upperville holiday rentals we have selected for you start as low as £185 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Upperville rentals

At Expedia, we put the best Upperville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Upperville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upperville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upperville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a holiday rental in Upperville?

Yes, there are holiday rentals close to the most popular sights in Upperville, or you can select a more secluded option if you're looking for a relaxing stay. Upperville is known for its restaurants.

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

Mountain View Bungalow in Front Royal: This holiday 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 holiday rentals are there in Upperville?

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

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 wider area.

What are holiday rentals like in Upperville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Upperville. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for families.