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Upperville Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Upperville vacation rentals

A modern kitchen with a wooden floor, a large window, and a kitchen island with stools.

1. 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.
The price is ￥21,159
￥42,346 total
includes taxes & fees
Oct 26 - Oct 27
Lunar Loft, with mountain views
A balcony with a table, two wine glasses, and a view of a fenced area with a truck and a building in the background.

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

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Markham
10.0 out of 10, Exceptional, (4 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 ￥34,010
￥41,538 total
includes taxes & fees
Oct 26 - Oct 27
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
A stone house with a chimney, surrounded by a well-maintained lawn and trees.

3. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (67 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
The price is ￥43,101
￥62,561 total
includes taxes & fees
Nov 15 - Nov 16
18th Century Stone Cottage minutes from historic Middleburg
A two-story house with a porch, surrounded by trees and grass.

4. 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 ￥27,114
￥60,711 total
includes taxes & fees
Nov 17 - Nov 18
1910 Farmhouse on 6 Acres • VA Wine Country
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, (2 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 ￥26,331
￥72,261 total
includes taxes & fees
Oct 27 - Oct 28
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
A two-story house with a balcony, string lights, and a swing.

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, (9 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
The price is ￥22,726
￥44,256 total
includes taxes & fees
Nov 1 - Nov 2
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, (8 reviews)
"Great little hideout! We loved this little place, accurately described and the communication was superb!"
United States
P H.
The price is ￥21,942
￥60,852 total
includes taxes & fees
Nov 16 - Nov 17
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.

8. 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 studio has potential but is not worth the price paid. Towels were old, mattress was soft, cobwebs were noticeable. Location is great."
United States
Kathleen
The price is ￥23,510
￥42,346 total
includes taxes & fees
Nov 2 - Nov 3
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
A wooden deck with outdoor furniture, including a table with a book and a cup, and a bench with patterned cushions.

9. 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, (1 review)
"This beautifully new cabin in the mountains was the perfect getaway location! So serene and beautiful! The front porch and back deck areas were the perfect setting to catch up with family! We will definitely be booking again. Rex and Meredith communicated with us perfectly before and during our stay. The indoors were just as beautiful as the outside with gorgeous bathrooms and unbelievably comfortable beds! Even our pooch loved the getaway!"
United States
Laura B.
The price is ￥29,442
￥58,578 total
includes taxes & fees
Nov 2 - Nov 3
Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries
A kitchen with a large island, wooden cabinets, a microwave, a coffee maker, and a window above the sink.

10. 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 ￥25,860
￥48,777 total
includes taxes & fees
Oct 29 - Oct 30
super cosy cottage with high speed internet!
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

11. 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, (45 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 ￥32,913
￥41,317 total
includes taxes & fees
Oct 29 - Oct 30
Blue Mountain Cabin, secluded, perfect for couples, near main road
A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

12. 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.
The price is ￥25,205
￥47,663 total
includes taxes & fees
Nov 3 - Nov 4
Mountain home w/ hot tub & sunroom
A spacious kitchen with modern appliances, a dining area with a large table and chairs, and a view through a glass door.

13. 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.
The price is ￥49,683
￥94,696 total
includes taxes & fees
Oct 26 - Oct 27
Spacious Modern Home on Middleburg Horse Farm
A covered outdoor deck with a fire pit, seating, and a view of the landscape.

14. 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.
The price is ￥35,970
￥81,610 total
includes taxes & fees
Nov 3 - Nov 4
Mountain Cabin Retreat | Hot Tub & Foosball |
A living room with a fireplace, a television mounted above it, and a large window with a view of trees.

15. NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
9.4 out of 10, Exceptional, (3 reviews)
"We were staying at the schoolhouse to go hiking and ride bikes. They house has been tastefully decorated. I enjoyed the quite community and the listening to the tree frogs at night. Front Royal has a few things you can enjoy such as the movie theatre, bakery and state park. I would highly recommend this propery."
United States
Suzanne J.
The price is ￥22,256
￥59,103 total
includes taxes & fees
Nov 8 - Nov 9
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
A wooden deck with a hot tub, steps, and a view of a forest.

16. 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 Foxwood Cabin | Hot Tub, Screened Porch, Grill
A hot tub with a view of a forest and a sunset.

17. 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 ￥21,315
￥56,184 total
includes taxes & fees
Nov 9 - Nov 10
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A wooden deck with outdoor furniture and a fire pit, surrounded by trees and a railing.

18. 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 ￥27,114
￥65,347 total
includes taxes & fees
Nov 9 - Nov 10
Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive
A deck with a hot tub, wooden chairs, and a table.

19. 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 ￥37,590
￥69,312 total
includes taxes & fees
Oct 28 - Oct 29
Mountain Views w/Hot Tub, 95” TV & Trail Access
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 ￥43,163
￥92,652 total
includes taxes & fees
Oct 28 - Oct 29
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Super clean, very quiet and excellent breakfast. Highly recommend."
Gayle Ellen 1-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Winchester

Find out more about Upperville

Search for holiday rentals in Upperville on Expedia! You can easily find your home rentals, villas, holiday apartments in Upperville using one of the methods below:

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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.