Upperville Holiday Rentals

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Our top choices for Upperville holiday rentals

Cozy cabin w/hot tub & game room

Cozy cabin w/hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (65 reviews)
"Tony always answered my texts immediately and was very easy to work with. The place was just as expected; it was comfortable and all amenities were available. Towels were laid out on the beds and the comforters were cute and cozy. The place is well worn; some appliances, mostly gas stove and microwave and towel hooks were very worn out but still useable. We loved all of the amenities, space and privacy in this cabin. We would stay here again. "
United States
Jenifer D.
The price is AU$442
includes taxes & fees
4 May - 5 May
Cozy cabin w/hot tub & game room

Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.

Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
Harpers Ferry
10.0 out of 10, Exceptional, (86 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
The price is AU$435
includes taxes & fees
21 Apr - 22 Apr
Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.

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, (31 reviews)
"Great stay! The place was clean, comfortable, and exactly as described. Host was responsive and helpful. Would definitely stay again."
United States
Wafaa L.
The price is AU$332
includes taxes & fees
23 Apr - 24 Apr
Blue Mountain Cabin, secluded, perfect for couples, near main road

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.4 out of 10, Exceptional, (13 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
The price is AU$502
includes taxes & fees
5 May - 6 May
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

Log Cabin w/ Hot Tub & Waterfront Patio!

Log Cabin w/ Hot Tub & Waterfront Patio!
Harpers Ferry
9.6 out of 10, Exceptional, (20 reviews)
"House was very clean and the hosts were responsive and very nice! Great place for a quiet weekend getaway. "
United States
Nicole H.
The price is AU$493
includes taxes & fees
20 Apr - 21 Apr
Log Cabin w/ Hot Tub & Waterfront Patio!

Cabin at the Gap | You Won't Believe the View!

Cabin at the Gap | You Won't Believe the View!
Harpers Ferry
The price is AU$475
includes taxes & fees
19 Apr - 20 Apr
Cabin at the Gap | You Won't Believe the View!

Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane
Linden
9.6 out of 10, Exceptional, (27 reviews)
"Great place. Very clean, lots of comfortable rooms. Nice outside area for dogs. "
United States
Lisa W.
The price is AU$625
includes taxes & fees
1 May - 2 May
Hidden Gem on Hidden Valley Lane

Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (4 reviews)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is AU$253
includes taxes & fees
22 Apr - 23 Apr
Luxury tiny home farm stay on historic property with hot tub in Stephens City

Forest chalet w/ hot tub & BBQ grill

Forest chalet w/ hot tub & BBQ grill
Harpers Ferry
9.2 out of 10, Wonderful, (32 reviews)
"Enjoyed the levels, hot tub, porch to get outside with my coffee, pet strolling area marvelous and washer/dryer."
United States
tracey b.
The price is AU$487
includes taxes & fees
21 Apr - 22 Apr
Forest chalet w/ hot tub & BBQ grill

Mountain Cabin • Views • Hot Tub • 5 Beds • Skyline Drive

Mountain Cabin • Views • Hot Tub • 5 Beds • Skyline Drive
Front Royal
10.0 out of 10, Exceptional, (5 reviews)
"Great property. Location is perfect with amazing view. Great house and amenities. "
United States
Michael M.
The price is AU$629
includes taxes & fees
19 Apr - 20 Apr
Mountain Cabin • Views • Hot Tub • 5 Beds • Skyline Drive

Blue Ridge Getaway - Sunset Views, A.T. Access

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (66 reviews)
"Very quiet cabin. Nicely situated between Charles Town and Harper’s Ferry. "
United States
Kelly R.
The price is AU$554
includes taxes & fees
26 Apr - 27 Apr
Blue Ridge Getaway - Sunset Views, A.T. Access

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (33 reviews)
"The host was great in communicating check in and check out instructions! We appreciated being able to park in the driveway and the fenced in back yard was also a nice amenity. Would definitely stay here again!"
United States
Katherine s.
The price is AU$432
includes taxes & fees
21 Apr - 22 Apr
Leesburg Hideaway- King Bed + Private Backyard

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
Harpers Ferry
9.6 out of 10, Exceptional, (45 reviews)
"The house was great, clean, beautiful setting."
United States
Brandon M.
The price is AU$484
includes taxes & fees
6 May - 7 May
Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (20 reviews)
"We enjoyed our stayed so much! This location is perfect. This property is so clean. "
United States
Nicole Z.
The price is AU$309
includes taxes & fees
5 May - 6 May
Mountain View Bungalow in Front Royal

18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (57 reviews)
"Loved out stay! "
United States
Emilee
The price is AU$543
includes taxes & fees
19 Apr - 20 Apr
18th Century Stone Cottage minutes from historic Middleburg

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
10.0 out of 10, Exceptional, (34 reviews)
"A very spacious and well equipped home to get away from it all; but, also convenient to Winchester for a night out. The fenced in areas for dogs were lovely."
United States
David A.
The price is AU$714
includes taxes & fees
22 Apr - 23 Apr
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!
Harpers Ferry
9.8 out of 10, Exceptional, (33 reviews)
"Would come back anytime, very scenic and easy check-in process"
United States
Mark F.
The price is AU$521
includes taxes & fees
20 Apr - 21 Apr
Rebels Rest - Cabin with Enchanting Sunset Views!

Mountain Cabin in the Woods, Near Wineries & More!

Mountain Cabin in the Woods, Near Wineries & More!
Harpers Ferry
8.8 out of 10, Excellent, (29 reviews)
"Nice place. "
United States
Patrick A.
The price is AU$336
includes taxes & fees
20 Apr - 21 Apr
Mountain Cabin in the Woods, Near Wineries & More!

The Juniper Cabin • Cozy Hideaway w/ Hot Tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (22 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
The price is AU$506
includes taxes & fees
5 May - 6 May
The Juniper Cabin • Cozy Hideaway w/ Hot Tub

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.8 out of 10, Exceptional, (16 reviews)
"Absolutely amazing place and stay! I could not possibly be more impressed and I look forward to coming back."
United States
Jasmine M.
The price is AU$542
includes taxes & fees
19 Apr - 20 Apr
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
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$309 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?

Breathtaking View with an Indoor Pool: This holiday home rental outside of Upperville is located in the mountains, and has an indoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Upperville?

Choose from 6 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 Dinosaur Land, or get outside and enjoy nature at Upperville Park. Sky Meadows State Park and RdV Vineyards 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.