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

Upperville Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Upperville vacation rentals

Property grounds

1. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.0 out of 10, Wonderful, (10 reviews)
"Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. "
United States
Haley M.
The price is ￥21,508
￥43,590 total
includes taxes & fees
Aug 19 - Aug 20
Lunar Loft, with mountain views
Terrace/patio

2. Peaceful mountain cabin in charming Berryville VA - next to river and brewery

Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Berryville
10.0 out of 10, Exceptional, (1 review)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveler
The price is ￥11,949
￥39,013 total
includes taxes & fees
Aug 23 - Aug 24
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Exterior

3. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (64 reviews)
"Loved out stay! "
United States
Emilee
The price is ￥43,813
￥63,594 total
includes taxes & fees
Aug 26 - Aug 27
18th Century Stone Cottage minutes from historic Middleburg
Property grounds

4. 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, (42 reviews)
"Beautiful, relaxing and quiet cabin, exceeded expectations."
United States
Johnathan B.
The price is ￥30,271
￥37,079 total
includes taxes & fees
Aug 19 - Aug 20
Blue Mountain Cabin, secluded, perfect for couples, near main road
Exterior

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

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
The price is ￥23,101
￥68,886 total
includes taxes & fees
Aug 23 - Aug 24
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Outdoor dining

6. "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 ￥34,572
￥42,395 total
includes taxes & fees
Aug 19 - Aug 20
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Exterior

7. 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 ￥28,536
￥62,426 total
includes taxes & fees
Aug 20 - Aug 21
1910 Farmhouse on 6 Acres • VA Wine Country
TV, fireplace, offices

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)
"Absolutely perfect spot for a leaf-peeping getaway. Clean, charming, romantic! Close to antiques, vineyards and Shenandoah!"
United States
Paul B.
The price is ￥33,159
￥74,030 total
includes taxes & fees
Aug 20 - Aug 21
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Terrace/patio

9. Mountain View Cottage | Hot Tub & Game Room

Mountain View Cottage | Hot Tub & Game Room
Front Royal
9.6 out of 10, Exceptional, (15 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is ￥30,430
￥85,053 total
includes taxes & fees
Sep 1 - Sep 2
Mountain View Cottage | Hot Tub & Game Room
Outdoor dining

10. Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!

Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!
Front Royal
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful time staying there during our time at upperville. The quiet nights in the hot tub were just what we needed! Matthew was a wonderful host and so helpful ! We hope to come back again "
United States
grace g.
The price is ￥28,696
￥88,448 total
includes taxes & fees
Aug 19 - Aug 20
Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!
Indoor spa tub

11. 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)
"Beautiful, quiet place to stay. Beds are very comfortable. Every room was very clean. "
United States
Alex H.
The price is ￥25,029
￥75,787 total
includes taxes & fees
Aug 24 - Aug 25
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Exterior

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

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
10.0 out of 10, Exceptional, (7 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
The price is ￥22,159
￥43,080 total
includes taxes & fees
Sep 9 - Sep 10
Cozy A frame cabin in quaint Front Royal. Dog friendly
Outdoor dining

13. Shenandoah Twilight | Hot Tub & Golden Hour Mountain Views

Shenandoah Twilight | Hot Tub & Golden Hour Mountain Views
Front Royal
9.0 out of 10, Wonderful, (2 reviews)
"Shenandoah Twilight is a beautiful spot tgats beautifully appointed. I really enjoyed my time there. "
United States
Wilson (Wally) W.
The price is ￥22,319
￥60,314 total
includes taxes & fees
Aug 24 - Aug 25
Shenandoah Twilight | Hot Tub & Golden Hour Mountain Views
Desk, iron/ironing board, WiFi (free), bed sheets

14. 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
9.8 out of 10, Exceptional, (28 reviews)
"Easy to get in and out, and the property was clean and tidy!"
United States
Cameron H.
The price is ￥23,898
￥43,590 total
includes taxes & fees
Aug 20 - Aug 21
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Exterior

15. 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, (17 reviews)
"We loved this house and will definitely use it again. That said, the bathroom "
United States
Margaret S.
The price is ￥25,507
￥70,336 total
includes taxes & fees
Aug 31 - Sep 1
Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6
Coffee/tea maker, fridge, microwave, oven

16. 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 ￥36,029
￥83,236 total
includes taxes & fees
Aug 24 - Aug 25
Spacious Modern Home on Middleburg Horse Farm
TV, offices

17. 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 ￥26,229
￥49,291 total
includes taxes & fees
Sep 15 - Sep 16
Mountain home w/ hot tub & sunroom
Property grounds

18. Mountain Cabin Retreat | Hot Tub & Foosball |

Mountain Cabin Retreat | Hot Tub & Foosball |
Front Royal
8.8 out of 10, Excellent, (10 reviews)
"Great property. Location is perfect with amazing view. Great house and amenities. "
United States
Michael M.
The price is ￥27,881
￥81,715 total
includes taxes & fees
Aug 19 - Aug 20
Mountain Cabin Retreat | Hot Tub & Foosball |
Interior

19. Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
10.0 out of 10, Exceptional, (34 reviews)
"It was a great place to stay and very clean."
United States
Chynna V.
Mountain cabin near national park & wineries
Interior

20. 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 ￥20,565
￥51,531 total
includes taxes & fees
Aug 31 - Sep 1
Bluemont home just minutes to wineries, breweries, hiking and more!
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

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"This is a great stop and a beautiful place. Highly recommended and will stay there again when in the area."
Timothy 1-night trip
Posted 8 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

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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Look no further and take a look at our great range of rental properties in Upperville!

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 6 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 Dinosaur Land, 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.