Upperville Vacation Rentals

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Vacation Rentals in Upperville

Lakefront Log Cabin w/ Dreamy Waterfront Patio!
2.0 star property
9.6 out of 10, Exceptional, (10)
"Exactly what we expected from the listing. Nice, clean, well appointed cabin on the lake with comfortable beds. Easy check-in and check-out procedures and good communication with management. "
United States
Kimberly J.
Lakefront Log Cabin w/ Dreamy Waterfront Patio!
Aslan's How - Cabin with Valley Views & Hot Tub!
2.0 star property
9.8 out of 10, Exceptional, (8)
"This very clean, well-kept cabin was a wonderful throw-back to grandma's cabin where you would want the whole family to spend a weekend. There were only two of us, but if you have a group you won't be disappointed! The views from the deck and hot tub at sunset were spectacular. Text communication from the property management was excellent."
United States
Joan R.
Aslan's How - Cabin with Valley Views & Hot Tub!
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
10.0 out of 10, Exceptional, (79)
"Absolutely delightful!"
United States
John M.
$104 nightly
The price is $280
Nov 10 - Nov 11
Total with taxes and fees
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
10.0 out of 10, Exceptional, (15)
"My boyfriend and our friends stayed here for a quick weekend trip for a wedding. The house was very cozy with an absolutely BEAUTIFUL view. We wish we could’ve stayed longer!"
United States
Kiersten M.
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Lake View Retreat - Cottage Near a Peaceful Lake!
9.6 out of 10, Exceptional, (21)
"Was really able to relax and enjoy during our brief stay. Would come again."
United States
Emily B.
Lake View Retreat - Cottage Near a Peaceful Lake!
Peaceful Lakefront Cottage with Mountain Views!
9.8 out of 10, Exceptional, (29)
"Really enjoyed stay home was great "
United States
zachary b.
Peaceful Lakefront Cottage with Mountain Views!
Cozy w Fire Pit, Deck, Screened Porch & WiFi
10.0 out of 10, Exceptional, (1)
"Our family had a cozy weekend at the cabin. Tony was super helpful and a great host. Thank you for sharing your lovely property with us!"
United States
Katrina S.
Cozy w Fire Pit, Deck, Screened Porch & WiFi
Secluded Cabin a Stone's Throw From the A.T.!
10.0 out of 10, Exceptional, (33)
"We were charmed by the house and pleased with all the amenities. We would definitely stay there again. "
United States
Jennifer T.
Secluded Cabin a Stone's Throw From the A.T.!
Rocky Ridge - Cabin w/ Hot Tub & Heavenly Views!
10.0 out of 10, Exceptional, (16)
"House located top on hill has a great scenic view. Property was nice,clean and spacious. "
United States
Sonjaay P.
Rocky Ridge - Cabin w/ Hot Tub & Heavenly Views!
Rebels Rest - Cabin with Enchanting Sunset Views!
9.8 out of 10, Exceptional, (31)
"Absolutely perfect setting to catch up with old friends. Great hosts."
United States
Sam H.
Rebels Rest - Cabin with Enchanting Sunset Views!
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
10.0 out of 10, Exceptional, (23)
"Loved this house for relaxing, enjoying nature and reconnecting with friends!"
United States
Ellen P.
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
9.4 out of 10, Exceptional, (27)
"We had a great stay and the house was perfect for a quick getaway weekend for our family. Close to wineries and explored Harper’s Ferry. Communication with the host Tony was great. We would stay here again!"
United States
Samantha W.
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
The River House
10.0 out of 10, Exceptional, (9)
"Excellent experience. Super clean house. Excellent location right on the river! Would definitely rent again!!"
United States
Casey W.
The River House
Blue Ridge Getaway - Sunset Views, A.T. Access
10.0 out of 10, Exceptional, (60)
"The house and property were very nice. Everything was as described. We enjoyed our stay."
United States
Sara S.
Blue Ridge Getaway - Sunset Views, A.T. Access
'thomson Farm' Classic Home < 10 Mi to Vineyards!
3.0 star property
'thomson Farm' Classic Home < 10 Mi to Vineyards!
Private apartment on a beautiful private farm!
8.8 out of 10, Excellent, (6)
"This little farm condo was absolutely perfect for our overnight stay. In fact, I wish we had the opportunity to stay longer. It was lovely to wake up and see chickens and other animals as well as hear the dogs barking. The view of the mountains was also lovely! We will definitely think of staying here again next time we visit our friends!"
United States
Matthew S.
Private apartment on a beautiful private farm!
Wild Hare Cottage
10.0 out of 10, Exceptional, (10)
"Perfect spot to relax for a long weekend. Easy drive to Middleburg, VA, wineries, breweries, and hiking. Would stay again. "
United States
Jennifer K.
Wild Hare Cottage
Lakefront House w/ Modern Comforts!
9.0 out of 10, Wonderful, (4)
"The house was very clean. The view of the lake and mountains was beautiful. The back deck with ping pong table was great. Nice that toiletries were provided. The property manager was responsive. The master bathroom should have a blind on the window. It was uncomfortable showering with a glass shower door and a window 2 feet from the shower, and the street not far from the house. Also, water poured out of the shower underneath the glass door. Would have liked to have some info printed out about...
United States
Cindy
Lakefront House w/ Modern Comforts!
Pretty Little Apt by the Train II
2.0 star property
9.6 out of 10, Exceptional, (5)
"Great time. Love this city"
United States
Barbara B.
Pretty Little Apt by the Train II
The Oculus - Huge Cabin with a Hot Tub!
9.6 out of 10, Exceptional, (24)
"The place was big and very roomy and comfortable. Very clean .. very nice. "
United States
Matthew S.
The Oculus - Huge Cabin with a 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

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 $280 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.

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?

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!: This vacation home rental outside of Upperville offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind.

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 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.