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Upperville Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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
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.
$248 nightly
The price is $266
Oct 4 - Oct 5
Total with taxes and fees
"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
9.2 out of 10, Wonderful, (11 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.
$239 nightly
The price is $272
Oct 5 - Oct 6
Total with taxes and fees
Lunar Loft, with mountain views
A wooden cabin with a porch, a bench, and a table.

3. 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, (3 reviews)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveler
$223 nightly
The price is $246
Oct 7 - Oct 8
Total with taxes and fees
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
A cabin with a deck, a covered outdoor area, and a gravel path leading to the entrance.

4. 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, (1 review)
"Great location. Great quiet atmosphere. Just one little thing - the steps are steep; so just something to be aware of."
United States
David S.
$389 nightly
The price is $429
Oct 27 - Oct 28
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.

5. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (66 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
$369 nightly
The price is $396
Oct 12 - Oct 13
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg
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
10.0 out of 10, Exceptional, (7 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
$254 nightly
The price is $280
Nov 1 - Nov 2
Total with taxes and fees
Cozy A frame cabin in quaint Front Royal. Dog friendly
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.

7. 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
$239 nightly
The price is $272
Oct 12 - Oct 13
Total with taxes and fees
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
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.
$399 nightly
The price is $402
Oct 7 - Oct 8
Total with taxes and fees
1910 Farmhouse on 6 Acres • VA Wine Country
A hot tub on a wooden deck with a view of a forest.

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.
$321 nightly
The price is $354
Oct 4 - Oct 5
Total with taxes and fees
Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

10. 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, (44 reviews)
"Beautiful, relaxing and quiet cabin, exceeded expectations."
United States
Johnathan B.
$214 nightly
The price is $236
Oct 14 - Oct 15
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
A wooden deck with a hot tub, a wooden bench, and a pair of shoes.

11. Getaway Cabin Retreat in Shenandoah Valley - Hot Tub, Sauna, Cold Plunge

Getaway Cabin Retreat in Shenandoah Valley - Hot Tub, Sauna, Cold Plunge
Shenandoah Farms
10.0 out of 10, Exceptional, (1 review)
$413 nightly
The price is $449
Oct 4 - Oct 5
Total with taxes and fees
Getaway Cabin Retreat in Shenandoah Valley - Hot Tub, Sauna, Cold Plunge
A wooden deck with outdoor furniture and a fire pit, surrounded by trees and a railing.

12. 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
9.0 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.
$340 nightly
The price is $375
Oct 5 - Oct 6
Total with taxes and fees
Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive
A wooden deck with a hot tub, steps, and a view of a forest.

13. 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.
$454 nightly
The price is $501
Oct 7 - Oct 8
Total with taxes and fees
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
A spacious living room with a fireplace, a dining area with a bench, and a large sliding glass door leading to an outdoor patio.

14. 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.
$439 nightly
The price is $484
Oct 13 - Oct 14
Total with taxes and fees
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

15. 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.
$287 nightly
The price is $307
Oct 27 - Oct 28
Total with taxes and fees
Mountain home w/ hot tub & sunroom
A dark wooden cabin with a welcoming sign, a front porch with steps, and a grill outside.

16. 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, (18 reviews)
"We loved this house and will definitely use it again. That said, the bathroom "
United States
Margaret S.
$398 nightly
The price is $439
Oct 5 - Oct 6
Total with taxes and fees
Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6
A spacious kitchen with modern appliances, a dining area with a large table and chairs, and a view through a glass door.

17. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (21 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.
$517 nightly
The price is $589
Oct 5 - Oct 6
Total with taxes and fees
Spacious Modern Home on Middleburg Horse Farm
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18. DC Wine Country Farmhouse | 5 Peaceful Acres

DC Wine Country Farmhouse | 5 Peaceful Acres
Loudoun County
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay. House is beautiful and clean and owner was highly responsive. "
United States
Michele B.
$426 nightly
The price is $465
Oct 5 - Oct 6
Total with taxes and fees
DC Wine Country Farmhouse | 5 Peaceful Acres
A cozy living room with a stone fireplace, leather sofas, and a large TV.

19. Delicious Cabin • Wine Country Retreat w/ Hot Tub

Delicious Cabin • Wine Country Retreat w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (18 reviews)
"Property and cabin was very clean and well stocked. Location was great to get to wineries. We saw deer and fox in the back yard, very peaceful."
United States
Edward
$387 nightly
The price is $427
Oct 5 - Oct 6
Total with taxes and fees
Delicious Cabin • Wine Country Retreat w/ Hot Tub
A covered outdoor deck with a fire pit, seating, and a view of the landscape.

20. 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.
$579 nightly
The price is $639
Oct 19 - Oct 20
Total with taxes and fees
Mountain Cabin Retreat | Hot Tub & Foosball |
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

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

8/10 Good
"Well sized clean room with comfortable, hot showers and large fridge. Well, engineered room layout from electrical connections to lighting and HVAC controls but wished fridge had freezer option."
Lisa 1-night trip
Posted 6 hours ago
Microtel Inn & Suites by Wyndham Winchester

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 $218 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.