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 wooden cabin with a porch, a bench, and a table.

1. 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, (4 reviews)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveller
The price is CA $107
CA $348 total
includes taxes & fees
Oct 18 - Oct 19
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
A fenced grassy field with a clear sky and distant hills.

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 CA $192
CA $388 total
includes taxes & fees
Oct 14 - Oct 15
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.

3. "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 $309
CA $378 total
includes taxes & fees
Oct 18 - Oct 19
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
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.
The price is CA $224
CA $642 total
includes taxes & fees
Nov 3 - Nov 4
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, (67 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
The price is CA $392
CA $566 total
includes taxes & fees
Oct 14 - Oct 15
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
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 $207
CA $401 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 CA $187
CA $541 total
includes taxes & fees
Nov 3 - Nov 4
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 CA $279
CA $471 total
includes taxes & fees
Oct 23 - Oct 24
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
A kitchen with a large island, wooden cabinets, a microwave, a coffee maker, and a window above the sink.

9. 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 $214
CA $416 total
includes taxes & fees
Oct 14 - Oct 15
super cosy cottage with high speed internet!
A two-story house with a porch, surrounded by trees and grass.

10. 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 $270
CA $581 total
includes taxes & fees
Oct 14 - Oct 15
1910 Farmhouse on 6 Acres • VA Wine Country
A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

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.
The price is CA $229
CA $432 total
includes taxes & fees
Nov 1 - Nov 2
Mountain home w/ hot tub & sunroom
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

12. 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 $299
CA $376 total
includes taxes & fees
Oct 14 - Oct 15
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.

13. 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)
The price is CA $357
CA $643 total
includes taxes & fees
Nov 10 - Nov 11
Getaway Cabin Retreat in Shenandoah Valley - Hot Tub, Sauna, Cold Plunge
A room with a foosball table, a dining table with chairs, and a sofa in the background.

14. 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 $270
CA $534 total
includes taxes & fees
Oct 22 - Oct 23
Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries
A kitchen with white cabinets, a wooden countertop, a stove, and a sink. There are two wooden stools and a clock on the wall.

15. Your Peaceful Getaway in the Blue Ridge.

Your Peaceful Getaway in the Blue Ridge.
Bluemont
8.0 out of 10, Very good, (5 reviews)
"Great experience booking and staying. Would absolutely book again!"
United States
Blake S.
The price is CA $214
CA $311 total
includes taxes & fees
Oct 19 - Oct 20
Your Peaceful Getaway in the Blue Ridge.
A stainless steel barbecue grill with four burners, positioned against a concrete wall with a wooden staircase in the background.

16. The Juniper Cabin • Cozy Hideaway w/ Hot Tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (24 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
The price is CA $247
CA $564 total
includes taxes & fees
Nov 3 - Nov 4
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
A wooden deck with outdoor furniture and a fire pit, surrounded by trees and a railing.

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
9.0 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 CA $217
CA $561 total
includes taxes & fees
Nov 3 - Nov 4
Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive
A spacious kitchen with modern appliances, a dining area with a large table and chairs, and a view through a glass door.

18. 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 $433
CA $844 total
includes taxes & fees
Oct 19 - Oct 20
Spacious Modern Home on Middleburg Horse Farm
A wooden deck with a hot tub, steps, and a view of a forest.

19. 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 $244
CA $657 total
includes taxes & fees
Nov 4 - Nov 5
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
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.
The price is CA $334
CA $847 total
includes taxes & fees
Nov 3 - Nov 4
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

Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"It’s a good place to attend weddings."
Umamaheshwar 1-night trip
Posted 8 hours ago
Lansdowne Resort and Spa

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 $311 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.