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

Upperville Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Upperville vacation 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.
$261 nightly
The price is $280
Nov 9 - Nov 10
Total with taxes and fees
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
A modern kitchen with a wooden floor, a large window, and a kitchen island with stools.

2. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.4 out of 10, Exceptional, (13 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.
$226 nightly
The price is $258
Nov 5 - Nov 6
Total with taxes and fees
Lunar Loft, with mountain views
A cabin with a deck, a covered outdoor area, and a gravel path leading to the entrance.

3. 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.
$397 nightly
The price is $438
Nov 5 - Nov 6
Total with taxes and fees
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
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.
$368 nightly
The price is $395
Nov 15 - Nov 16
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg
A two-story house with a porch, surrounded by trees and grass.

5. 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.
$355 nightly
The price is $357
Dec 1 - Dec 2
Total with taxes and fees
1910 Farmhouse on 6 Acres • VA Wine Country
A wooden bridge leading to a house surrounded by lush greenery and purple flowers.

6. 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.
$285 nightly
The price is $324
Nov 10 - Nov 11
Total with taxes and fees
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
A two-story house with a balcony, surrounded by trees and snow.

7. 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.
$233 nightly
The price is $257
Nov 11 - Nov 12
Total with taxes and fees
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.

8. 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, (8 reviews)
"Great little hideout! We loved this little place, accurately described and the communication was superb!"
United States
P H.
$336 nightly
The price is $371
Nov 16 - Nov 17
Total with taxes and fees
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
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)
"Easy to get in and out, and the property was clean and tidy!"
United States
Cameron H.
$218 nightly
The price is $249
Nov 5 - Nov 6
Total with taxes and fees
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.
$320 nightly
The price is $353
Nov 9 - Nov 10
Total with taxes and fees
Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries
A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

11. Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
Front Royal
9.0 out of 10, Wonderful, (32 reviews)
"The cottage was amazing!! The hot tub was great and check in was super easy :) Internet and phone service were very good, and the cottage was stocked with all the kitchen utensils and linens we could have needed!"
United States
Mollie S.
$296 nightly
The price is $316
Nov 5 - Nov 6
Total with taxes and fees
Mountain home w/ hot tub & sunroom
A covered outdoor deck with a fire pit, seating, and a view of the landscape.

12. Mountain Cabin Retreat | Hot Tub & Foosball |

Mountain Cabin Retreat | Hot Tub & Foosball |
Front Royal
8.8 out of 10, Excellent, (11 reviews)
"Amazing house in an amazing place. The deck, view and sunsets are great stress reducers. Hope to visit again!"
United States
Christine T.
$425 nightly
The price is $468
Dec 1 - Dec 2
Total with taxes and fees
Mountain Cabin Retreat | Hot Tub & Foosball |
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

13. 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.
$226 nightly
The price is $249
Nov 5 - Nov 6
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
A living room with a television, a sofa with a pillow marked with the number 6, a small table, and a window with a view of trees.

14. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (22 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.
$493 nightly
The price is $562
Nov 5 - Nov 6
Total with taxes and fees
Spacious Modern Home on Middleburg Horse Farm
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.
$406 nightly
The price is $448
Nov 16 - Nov 17
Total with taxes and fees
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
A kitchen with a large island, wooden cabinets, a microwave, a coffee maker, and a window above the sink.

16. 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
$262 nightly
The price is $299
Dec 1 - Dec 2
Total with taxes and fees
super cosy cottage with high speed internet!
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.
$345 nightly
The price is $381
Nov 8 - Nov 9
Total with taxes and fees
Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive
A two-story house with a balcony, a hot tub, and a stone pathway leading to the entrance.

18. Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6

Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6
Front Royal
10.0 out of 10, Exceptional, (21 reviews)
"We loved this house and will definitely use it again. That said, the bathroom "
United States
Margaret S.
$410 nightly
The price is $452
Nov 17 - Nov 18
Total with taxes and fees
Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6
A kitchen with white cabinets, a wooden countertop, a stove, and a sink. There are two wooden stools and a clock on the wall.

19. Your Peaceful Getaway in the Blue Ridge.

Your Peaceful Getaway in the Blue Ridge.
Bluemont
8.0 out of 10, Very good, (9 reviews)
"Great experience booking and staying. Would absolutely book again!"
United States
Blake S.
$198 nightly
The price is $218
Nov 30 - Dec 1
Total with taxes and fees
Your Peaceful Getaway in the Blue Ridge.
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.
$509 nightly
The price is $561
Dec 1 - Dec 2
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upperville Hotel Reviews

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

10/10 Excellent
"Indoor pool was nice. Restaurant attached was great. Free breakfast was good. Location was quiet and near Harper's Ferry."
Herbert 1-night trip
Posted 13 hours ago
Clarion Inn Harpers Ferry - Charles Town

Find out more about Upperville

Everything you need to know about Upperville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upperville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Upperville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Upperville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $205 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Upperville rentals

At Expedia, we put the best Upperville vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.