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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Upperville vacation rentals

A stone house with a chimney, surrounded by a well-maintained lawn and trees.

1. 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 CA $389
CA $564 total
includes taxes & fees
Oct 18 - Oct 19
18th Century Stone Cottage minutes from historic Middleburg
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 CA $307
CA $376 total
includes taxes & fees
Oct 18 - Oct 19
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
A fenced grassy field with a clear sky and distant hills.

3. 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 CA $191
CA $387 total
includes taxes & fees
Oct 20 - Oct 21
Lunar Loft, with mountain views
A spacious kitchen with modern appliances, a dining area with a large table and chairs, and a view through a glass door.

4. 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 CA $423
CA $827 total
includes taxes & fees
Oct 19 - Oct 20
Spacious Modern Home on Middleburg Horse Farm
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, (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.
The price is CA $238
CA $657 total
includes taxes & fees
Oct 27 - Oct 28
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
A two-story house with a porch, surrounded by trees and grass.

6. 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 CA $246
CA $552 total
includes taxes & fees
Nov 16 - Nov 17
1910 Farmhouse on 6 Acres • VA Wine Country
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 CA $198
CA $554 total
includes taxes & fees
Oct 20 - Oct 21
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

8. 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 CA $297
CA $374 total
includes taxes & fees
Oct 18 - Oct 19
Blue Mountain Cabin, secluded, perfect for couples, near main road
A dark wooden cabin with a welcoming sign, a front porch with steps, and a grill outside.

9. 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 CA $524
CA $986 total
includes taxes & fees
Oct 25 - Oct 26
Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6
A room with a foosball table, a dining table with chairs, and a sofa in the background.

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, (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 CA $267
CA $528 total
includes taxes & fees
Oct 22 - Oct 23
Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries
A covered outdoor area with a fire pit, seating, and a view of the landscape.

11. Mountaintop Cottage | Private Hot Tub

Mountaintop Cottage | Private Hot Tub
Front Royal
9.8 out of 10, Exceptional, (27 reviews)
"Excellent location and amazing reviews. Would definitely plan to arrive while it’s light out for the first time as the road does get a little rough at the top but we did all make it in 2WD vehicles"
United States
Sara Z.
The price is CA $526
CA $986 total
includes taxes & fees
Nov 8 - Nov 9
Mountaintop Cottage | Private Hot Tub
A two-story house with a balcony, a hot tub, and a circular wooden structure.

12. 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 CA $387
CA $912 total
includes taxes & fees
Oct 27 - Oct 28
Luxury Mountain Retreat w/ Valley Views, 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.

13. 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 CA $212
CA $387 total
includes taxes & fees
Oct 18 - Oct 19
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
A two-story house with a balcony, string lights, and a swing.

14. 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 CA $205
CA $401 total
includes taxes & fees
Nov 2 - Nov 3
Cozy A frame cabin in quaint Front Royal. Dog friendly
A hot tub on an outdoor deck with a view of trees and hills.

15. Mountain View Cottage | Hot Tub & Game Room

Mountain View Cottage | Hot Tub & Game Room
Front Royal
9.8 out of 10, Exceptional, (17 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is CA $440
CA $977 total
includes taxes & fees
Nov 3 - Nov 4
Mountain View Cottage | Hot Tub & Game Room
A covered outdoor deck with a fire pit, seating, and a view of the landscape.

16. 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 CA $332
CA $842 total
includes taxes & fees
Nov 3 - Nov 4
Mountain Cabin Retreat | Hot Tub & Foosball |
Local wineries, breweries, and small-town charm in Front Royal

17. Mountain Views w/Hot Tub, 95” TV & Trail Access

Mountain Views w/Hot Tub, 95” TV & Trail Access
Shenandoah Farms
10.0 out of 10, Exceptional, (1 review)
"We were looking for a comfortable home base to explore Front Royal and Skyline Plaza, and this was perfect! A modernized home with enough amenities that we were tempted every day to just stay “home!” The kids loved the reading nook and cozy sitting areas, and the fire pit and clean, working hot tub were big pluses as well. Kitchen was roomy, with great appliances and plenty of counter space. Beds were comfortable. Bathrooms were nice and modern. Lots of closet space, too. When we left, the kids...
United States
Joshua J.
The price is CA $367
CA $666 total
includes taxes & fees
Oct 26 - Oct 27
Mountain Views w/Hot Tub, 95” TV & Trail Access
A kitchen with a large island, wooden cabinets, a microwave, a coffee maker, and a window above the sink.

18. 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 CA $233
CA $443 total
includes taxes & fees
Oct 18 - Oct 19
super cosy cottage with high speed internet!
A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

19. 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 CA $227
CA $433 total
includes taxes & fees
Nov 3 - Nov 4
Mountain home w/ hot tub & sunroom
A wooden deck with a hot tub, steps, and a view of a forest.

20. 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 CA $255
CA $669 total
includes taxes & fees
Nov 4 - Nov 5
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
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
"clean, nice, left before breakfast was ready so I can't speak on it, parking lot well lite"
Amy 1-night trip
Posted 13 hours ago
La Quinta 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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upperville vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upperville vacation rentals we have selected for you start as low as CA $307 per night. Entering your travel dates in the search wizard 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.