Upperville Holiday Rentals

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Holiday Rentals in Upperville

18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (47)
"What a peaceful place and wonderful views."
The price is AU$620
includes taxes & fees
26 Oct - 27 Oct
18th Century Stone Cottage minutes from historic Middleburg
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
10.0 out of 10, Exceptional, (75)
"Wonderful view from the sunroom. Peaceful and rejuvenating stay in this welcoming home. "
The price is AU$437
includes taxes & fees
14 Oct - 15 Oct
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
Beautifully Restored Log Cabin in Bluemont, VA
10.0 out of 10, Exceptional, (39)
"We had a blast here. Great cabin and great location!"
Beautifully Restored Log Cabin in Bluemont, VA
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
9.2 out of 10, Wonderful, (12)
"Four family members stayed for a four day weekend. The place was spotless when we arrived and all amenities are as described. The location is perfect for visiting Harpers Ferry, Shepherdstown, and Antietam. We had wonderful time."
The price is AU$794
includes taxes & fees
14 Oct - 15 Oct
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
10.0 out of 10, Exceptional, (47)
"Beautiful area"
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
9.4 out of 10, Exceptional, (26)
"The house was very clean upon arrival. We enjoyed spending time in the hot tub and playing pool on a kid’s pool table. It was close the Harper’s Ferry. We also saw deer very close both days we were there, and we loved this!!"
The price is AU$600
includes taxes & fees
14 Oct - 15 Oct
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
10.0 out of 10, Exceptional, (95)
"Very nice relaxing getaway, quite how do you spell quiet and serene location. "
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
9.2 out of 10, Wonderful, (61)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
The price is AU$418
includes taxes & fees
28 Oct - 29 Oct
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
Breathtaking View with an Indoor Pool
9.8 out of 10, Exceptional, (259)
"Great Property"
Breathtaking View with an Indoor Pool
The Apple Mountain House
9.8 out of 10, Exceptional, (6)
"Amazing place to relax."
The price is AU$792
includes taxes & fees
20 Oct - 21 Oct
The Apple Mountain House
Wild And Wonderful Silos
9.6 out of 10, Exceptional, (7)
"Heated mattress was the best. Thank you! "
The price is AU$467
includes taxes & fees
15 Oct - 16 Oct
Wild And Wonderful Silos
Gruner Bungalow at Otium Cellars
9.8 out of 10, Exceptional, (102)
"Place exceeded expectations and the host was very accommodating very clean and stocked was able enjoy the stay on wonderful property "
Gruner Bungalow at Otium Cellars
Apple Mountain Retreat
10.0 out of 10, Exceptional, (19)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is AU$362
includes taxes & fees
14 Oct - 15 Oct
Apple Mountain Retreat
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
10.0 out of 10, Exceptional, (16)
"The house is well maintained and furnished, and the outdoor space is lovely. We had a great weekend in Leesburg and would come again. "
The price is AU$580
includes taxes & fees
19 Oct - 20 Oct
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Historical cottage in the town of Paris
9.8 out of 10, Exceptional, (48)
"we enjoy our stay everytime"
Historical cottage in the town of Paris
Lakefront Log Cabin w/ Dreamy Waterfront Patio!
2.0 star property
9.8 out of 10, Exceptional, (7)
"Beautiful property. Nice views of the lake."
The price is AU$532
includes taxes & fees
30 Oct - 31 Oct
Lakefront Log Cabin w/ Dreamy Waterfront Patio!
Escape to Shenandoah River, Hot Tub after a Hike!
10.0 out of 10, Exceptional, (50)
"Very nice updated home in a beautiful peaceful setting. I would highly recomend it!"
The price is AU$581
includes taxes & fees
14 Oct - 15 Oct
Escape to Shenandoah River, Hot Tub after a Hike!
Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!
9.6 out of 10, Exceptional, (8)
"House was perfect for our needs! Clean, well equipped, nicely decorated, quiet. Hot tub was super clean and very relaxing! Close to Harper’s Ferry. Host was quick to respond and checked in on us by text. "
The price is AU$516
includes taxes & fees
14 Oct - 15 Oct
Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!
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. "
The price is AU$681
includes taxes & fees
20 Oct - 21 Oct
The Oculus - Huge Cabin with a Hot Tub!
Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.
7.6 out of 10, Good, (26)
"Easy check in. House is located in a cluster of homes. Photos are misleading. Cleanliness was sub par. Linens and towels from previous guests were laying on top of the washer. Wasn’t sure if the linens and towels that we did have were even clean and fresh. Home smelled of alcohol and cigarettes. Good location."
Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upperville holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Upperville holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upperville holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upperville holiday rentals we have selected for you start as low as AU$362 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Upperville rentals

At Expedia, we put the best Upperville holiday 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 holiday.

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 holiday rental in Upperville?

Yes, there are holiday rentals close to the most popular sights in Upperville, or you can select a more secluded option if you're looking for a relaxing stay. Upperville is known for its restaurants.

What are some of the best holiday rentals that Upperville has to offer?

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex: This holiday home rental outside of Upperville is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a private garden and 1 hot tub.

How many holiday rentals are there in Upperville?

Choose from 5 Expedia holiday rentals in Upperville for a memorable holiday.

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 wider area.

What are holiday rentals like in Upperville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Upperville. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for families.