Upperville Vacation Rentals

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Vacation Rentals in Upperville

Smart TV, DVD player, books, video library
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
10.0 out of 10, Exceptional, (28)
"This little cabin was great!! Comfortable beds. Very clean. Brigid the host was so responsive. Instructions were very clear. She even answered our questions about recommendations for a goos hiking trail! Highly recommend! I hope we will be back."
The price is CA $199
CA $451 total
includes taxes & fees
May 28 - May 29
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Interior
Escape to Shenandoah River, Hot Tub after a Hike!
10.0 out of 10, Exceptional, (38)
"Super clean. Super easy check in & check out. Quiet and beautiful setting. The windows bring the outdoors in. Fabulous to watch the electric storm through those big beautiful windows from the comfort of the couch."
The price is CA $224
CA $538 total
includes taxes & fees
Jun 5 - Jun 6
Escape to Shenandoah River, Hot Tub after a Hike!
Fridge, microwave, oven, stovetop
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (227)
"Fantastic spot to spend a few days. Incredible house, fantastic amenities, and a beautiful location."
Breathtaking views with an indoor private pool, come escape with us
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Terrace/patio
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
9.2 out of 10, Wonderful, (211)
"It was fun to play parcheesi again!"
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
Exterior
18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (16)
"We had a nice stay in a lovely rural location with nice outdoor terrace and quiet street for a long walk. Communication with the host was simple and straight forward."
The price is CA $370
CA $535 total
includes taxes & fees
Jun 9 - Jun 10
18th Century Stone Cottage minutes from historic Middleburg
Exterior
New Wine Horse Country 10 Acre Lux Retreat amid historic sites. Stunning Views!
9.8 out of 10, Exceptional, (7)
"Great location, beautifully appointed - wish we’d had more time to enjoy the property."
The price is CA $409
CA $710 total
includes taxes & fees
May 26 - May 27
New Wine Horse Country 10 Acre Lux Retreat amid historic sites. Stunning Views!
Fridge, microwave, stovetop, dishwasher
Charming Home with Yard Near Shenandoah River!
9.6 out of 10, Exceptional, (7)
"The hosts received a notice that we had lost heat at the house. We actually did not, but they were out the next morning to check the furnace and brought two space heaters we did not have to use. Really enjoyed our stay."
Charming Home with Yard Near Shenandoah River!
Property grounds
The Oculus - Huge Cabin with a Hot Tub!
10.0 out of 10, Exceptional, (11)
"This property is so wonderful. Great location. Wonderfully comfortable beds! And very clean! We look forward to coming back!"
The Oculus - Huge Cabin with a Hot Tub!
Property grounds
Family Gathering Space with a PRIVATE TRAIL WALK TO WINE!
10.0 out of 10, Exceptional, (36)
"We visited for a friends weekend and loved our stay. The bedrooms and communal areas were comfortable and great for a party of 7. The hot tub and outdoor fireplace were a hit. The property was peaceful. We didn’t walk to winery bc it was raining but we did drive (a minute) there and that was a lovely winery trip. The host was proactive asking if we needed anything before and during our stay. She was helpful w recommendation for restaurants and kind to offer any help while we were there (which...
Family Gathering Space with a PRIVATE TRAIL WALK TO WINE!
Private kitchen
The Pond Cabin: Hot Tub & Stocked Pond
10.0 out of 10, Exceptional, (21)
"It was wonderful! Nice wineries in area and a nice house to be together in. The scenery and yard is beautiful"
The price is CA $409
CA $763 total
includes taxes & fees
May 27 - May 28
The Pond Cabin: Hot Tub & Stocked Pond
Property grounds
Rustic Log Cabin with Private Dock on the Lake!
9.6 out of 10, Exceptional, (9)
"The location tucked away on the lake with a dock and kayaks and gravity lounge chairs, fireplace, large dock and gas grill were fabulous."
Rustic Log Cabin with Private Dock on the Lake!
Smart TV, fireplace, table tennis, books
Hot Tub, Poker Table, River Access & Kayaks and Wineries
10.0 out of 10, Exceptional, (5)
"It was great. Nice property, awesome location. Very private"
The price is CA $220
CA $578 total
includes taxes & fees
Jun 5 - Jun 6
Hot Tub, Poker Table, River Access & Kayaks and Wineries
Property grounds
Terra Alta - Incredible River Views and Hot Tub!
9.8 out of 10, Exceptional, (44)
"Stayed here for work. Had 5 guys at the house. Plenty of room and great deck to hang out on."
Terra Alta - Incredible River Views and Hot Tub!
Fridge, microwave, oven, stovetop
Cozy home near Casino, Breweries, Historical attractions, National Park & more
10.0 out of 10, Exceptional, (12)
"The home is beautiful! The owners did an amazing job to make us feel welcomed and at home. They provided us we unexpected amenities like coffee creamer, bottle water and even a bottle of wine. We greatly appreciated the free Netflix especially since ti rained during part of our stay. The location is ideal for our weekend adventures."
Cozy home near Casino, Breweries, Historical attractions, National Park & more
Smart TV, table tennis, books, offices
Gruner Bungalow at Otium Cellars
9.8 out of 10, Exceptional, (83)
"This was a beautiful home for a 30 something Bachelorette Weekend. The proximity to the tasting room was convenient and the grounds were beautiful. Our groups had an excellent time and hope to be back!"
Gruner Bungalow at Otium Cellars
Exterior
Dome Of Your Dreams!
8.4 out of 10, Very good, (42)
"We chose the Dome for our week long stay due to it's proximity to the state parks in northern Virginia, AND we'd choose to stay her again. We visited several new establishments, breweries, distilleries, and restaurants that have popped up or have missed since moving to central Virginia. We were out of the house everyday and then most nights came back and turned in for the evening. We couldn't zone out in front of the TV on the main living area because there isn't one. There is one downstairs...
Dome Of Your Dreams!
Property grounds
Wolf Den - Airy Cabin w/ Incredible Valley Views!
10.0 out of 10, Exceptional, (7)
"Cozy cabin with beautiful views! House was nicely furnished with everything needed for a pleasant stay. House looks exactly like the pics! Owners were very responsive and check in was so easy! House is at the top of a mountain so be prepared!"
Wolf Den - Airy Cabin w/ Incredible Valley Views!
Property grounds
Historic and Updated Farmhouse Built in 1808
10.0 out of 10, Exceptional, (113)
"Neat little home built in the 1800’s. Home was neat and clean with everything we needed for our stay in the Leesburg area. A bit out of town, but it was only 15 minutes from our daughter’s house."
Historic and Updated Farmhouse Built in 1808
Dining
Harpers Ferry Cabin - Walk to Private Lake!
9.6 out of 10, Exceptional, (8)
"Super clean and exactly as advertised! So quiet and peaceful. No skimping on toilet paper - the nice stuff is provided! That gives you the idea of quality there."
Harpers Ferry Cabin - Walk to Private Lake!
Property grounds
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
10.0 out of 10, Exceptional, (21)
"Thank you Asad and Erika, my fiance and I had an amazing few days on top of the beautiful mountains. The house was beautiful, very clean, fully stocked, and I enjoyed the adorable Bear theme through out the home, so many details! So inviting, warm and even had a beautiful piano. There was various games and activities in the home, not to mention about 15 minutes from downtown! Great location! We enjoyed the amazing views, and the peace! We even hired an amazing local photographer Joe Stein...
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Don't see what you're looking for?
See all available properties in Upperville
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.

Other types of properties in Upperville you may be interested in

Exterior
La Quinta Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (1344)
"We enjoyed our stay at la quinta. It is clean and pet friendly."
The price is CA $145
CA $158 total
includes taxes & fees
May 26 - May 27
La Quinta Inn & Suites by Wyndham Winchester
Free daily buffet breakfast
Clarion Hotel & Conference Center Leesburg
2.5 star property
6.8 out of 10, (869)
"Excelente experiencia "
The price is CA $149
CA $171 total
includes taxes & fees
Jun 9 - Jun 10
Clarion Hotel & Conference Center Leesburg
Lobby
Microtel Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (776)
"Its was a really nice hotel the people were friendly 🙂 very clean and a reasonable price i would stay there again without a doubt thank you"
The price is CA $115
CA $125 total
includes taxes & fees
Jun 2 - Jun 3
Microtel Inn & Suites by Wyndham Winchester
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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?

Breathtaking views with an indoor private pool, come escape with us: This vacation home rental outside of Upperville is located in the mountains and has an indoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Upperville?

Choose from 5 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 Virginia River Trips, or get outside and enjoy nature at Sky Meadows State Park. Naked Mountain Winery & Vineyards and Bluemont Vineyard 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.

Recent reviews of Upperville properties
Expedia verified reviews