Upperville Holiday Rentals

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Our top choices for Upperville holiday rentals

'thomson Farm' Classic Home < 10 Mi to Vineyards!

'thomson Farm' Classic Home < 10 Mi to Vineyards!
3.0 star property
Leesburg
The price is NZ$3,113
includes taxes & fees
3 Apr - 4 Apr
'thomson Farm' Classic Home < 10 Mi to Vineyards!

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, (12 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 NZ$660
includes taxes & fees
21 Mar - 22 Mar
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

Quaint Royal Cottage @ Historic Leesburg

Quaint Royal Cottage @ Historic Leesburg
Leesburg's Old and Historic District
10.0 out of 10, Exceptional, (10 reviews)
"Great location in a great town!"
United States
Gigi D.
The price is NZ$911
includes taxes & fees
23 Mar - 24 Mar
Quaint Royal Cottage @ Historic Leesburg

Cottage on King | Charming Historic Leesburg Home

Cottage on King | Charming Historic Leesburg Home
Leesburg's Old and Historic District
9.6 out of 10, Exceptional, (69 reviews)
"the cottage had everything we needed. "
United States
christa S.
The price is NZ$903
includes taxes & fees
22 Mar - 23 Mar
Cottage on King | Charming Historic Leesburg Home

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Front Royal
9.6 out of 10, Exceptional, (17 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is NZ$378
includes taxes & fees
31 Mar - 1 Apr
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

The Foxwood Cabin | Hot Tub, Screened Porch, Grill

The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Front Royal
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful, quiet place to stay. Beds are very comfortable. Every room was very clean. "
United States
Alex H.
The price is NZ$873
includes taxes & fees
9 Apr - 10 Apr
The Foxwood Cabin | Hot Tub, Screened Porch, Grill

Royal Heritage Home @ Historic Leesburg

Royal Heritage Home @ Historic Leesburg
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (40 reviews)
"Great location, would stay again."
United States
Eric D S.
The price is NZ$911
includes taxes & fees
23 Mar - 24 Mar
Royal Heritage Home @ Historic Leesburg

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Harpers Ferry
9.8 out of 10, Exceptional, (107 reviews)
"Booked this property for my entire extended family for a wedding. It was perfect for the 18 of us with plenty of room for everyone to have their own space to relax. The common areas were also big enough for us all to have a conversation. "
United States
Staci H.
The price is NZ$1,317
includes taxes & fees
27 Mar - 28 Mar
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

The Cottage on Royal - Historic Leesburg Home

The Cottage on Royal - Historic Leesburg Home
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (19 reviews)
"Delightful cottage, super convenient, and our host was extremely nice and attentive. "
United States
Mark M.
The price is NZ$868
includes taxes & fees
23 Mar - 24 Mar
The Cottage on Royal - Historic Leesburg Home

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
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 NZ$546
includes taxes & fees
26 Mar - 27 Mar
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Romantic African-Inspired Studio on Alpaca Farm – Under the Stars

Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
The Plains
9.8 out of 10, Exceptional, (9 reviews)
"The entire stay was nothing but exceptional. The host was very informative, knowledgeable, and helped make the stay all it can be and then some."
United States
Joe D.
The price is NZ$845
includes taxes & fees
19 Apr - 20 Apr
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars

Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly

Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly
Harpers Ferry
10.0 out of 10, Exceptional, (6 reviews)
"Very clean, great amenities, comfortable!"
United States
James
The price is NZ$849
includes taxes & fees
24 Mar - 25 Mar
Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly

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)
"Very cozy cabin for two, great for a secluded getaway within range of great places to visit. Had everything we needed."
United States
Tom C.
The price is NZ$395
includes taxes & fees
1 Apr - 2 Apr
Blue Mountain Cabin, secluded, perfect for couples, near main road

A unique mountaintop getaway overlooking Willow Croft Winery.

A unique mountaintop getaway overlooking Willow Croft Winery.
Leesburg
10.0 out of 10, Exceptional, (115 reviews)
"Wonderful home with outstanding hosts! Will hope to stay here every time we visit Leesburg!"
United States
Ethan R.
The price is NZ$1,074
includes taxes & fees
14 Apr - 15 Apr
A unique mountaintop getaway overlooking Willow Croft Winery.

Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street

Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Warrenton
10.0 out of 10, Exceptional, (5 reviews)
"I love staying here! It's cozy and comfortable and in a perfect location. "
United States
Jenny D.
The price is NZ$457
includes taxes & fees
26 Mar - 27 Mar
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (33 reviews)
"Lovely property, really nicely furnished and clean. Brilliant location for lots of places locally and close enough to walk into Leesburg itself to get ice cream!"
United Kingdom
Rachael B.
The price is NZ$531
includes taxes & fees
23 Mar - 24 Mar
Leesburg Hideaway- King Bed + Private Backyard

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (14 reviews)
"Excellent place to stay. Shelly is an excellent host. Nice location "
United States
Lisa H.
The price is NZ$734
includes taxes & fees
24 Mar - 25 Mar
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Shenandoah Twilight | Cozy Cabin w/ hot tub

Shenandoah Twilight | Cozy Cabin w/ hot tub
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 NZ$785
includes taxes & fees
23 Mar - 24 Mar
Shenandoah Twilight | Cozy Cabin w/ hot tub

Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping

Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping
Leesburg
8.8 out of 10, Excellent, (11 reviews)
"We loved the little getaway in the woods that was so conveniently close to Leesburg. It was a wonderful stay!"
United States
Caitlin J.
The price is NZ$507
includes taxes & fees
15 Apr - 16 Apr
Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping
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 favorite 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 depends 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 NZ$374 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 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 Blue Ridge Regional Park, 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.