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Upperville Holiday Rentals

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Our top choices for Upperville holiday rentals

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 NZ$498
includes taxes & fees
9 Nov - 10 Nov
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

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.
The price is NZ$456
includes taxes & fees
9 Nov - 10 Nov
Lunar Loft, with mountain views

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.
The price is NZ$747
includes taxes & fees
9 Nov - 10 Nov
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

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 NZ$704
includes taxes & fees
15 Nov - 16 Nov
18th Century Stone Cottage minutes from historic Middleburg

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.
The price is NZ$635
includes taxes & fees
1 Dec - 2 Dec
1910 Farmhouse on 6 Acres • VA Wine Country

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.
The price is NZ$575
includes taxes & fees
10 Nov - 11 Nov
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

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.
The price is NZ$457
includes taxes & fees
11 Nov - 12 Nov
Cozy A frame cabin in quaint Front Royal. Dog friendly

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.
The price is NZ$630
includes taxes & fees
15 Nov - 16 Nov
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

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.
The price is NZ$456
includes taxes & fees
8 Nov - 9 Nov
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

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 NZ$627
includes taxes & fees
9 Nov - 10 Nov
Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries

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.
Mountain home w/ hot tub & sunroom

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.
The price is NZ$831
includes taxes & fees
1 Dec - 2 Dec
Mountain Cabin Retreat | Hot Tub & Foosball |

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.
The price is NZ$428
includes taxes & fees
8 Nov - 9 Nov
Blue Mountain Cabin, secluded, perfect for couples, near main road

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.
The price is NZ$1,030
includes taxes & fees
1 Dec - 2 Dec
Spacious Modern Home on Middleburg Horse Farm

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 NZ$763
includes taxes & fees
9 Nov - 10 Nov
The Foxwood Cabin | Hot Tub, Screened Porch, Grill

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
The price is NZ$523
includes taxes & fees
1 Dec - 2 Dec
super cosy cottage with high speed internet!

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 NZ$677
includes taxes & fees
8 Nov - 9 Nov
Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive

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.
The price is NZ$785
includes taxes & fees
17 Nov - 18 Nov
Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6

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.
The price is NZ$382
includes taxes & fees
30 Nov - 1 Dec
Your Peaceful Getaway in the Blue Ridge.

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 NZ$974
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

Find out more about Upperville

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Upperville holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Upperville. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Upperville. Seeing all the best attractions is bound to make you fall in love with Upperville. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Upperville short-term rentals, that won’t be hard to do.

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.