Upperville Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Upperville vacation rentals

Property grounds

Cabin in Front Royal

Blue Mountain Cabin, secluded, perfect for couples, near main road
10.0 out of 10, Exceptional, (30 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 ￥29,650
￥36,318 total
includes taxes & fees
Mar 2 - Mar 3
Blue Mountain Cabin, secluded, perfect for couples, near main road

Chalet in Harpers Ferry

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
9.2 out of 10, Wonderful, (31 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 ￥25,804
￥46,696 total
includes taxes & fees
Mar 9 - Mar 10
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Dining

Cabin in Harpers Ferry

Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
10.0 out of 10, Exceptional, (84 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
The price is ￥22,471
￥52,252 total
includes taxes & fees
Mar 2 - Mar 3
Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
Outdoor dining

Cabin in Harpers Ferry

Cozy cabin w/private hot tub & game room
9.0 out of 10, Wonderful, (64 reviews)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
United States
Chelsey-Ann
The price is ￥23,532
￥48,291 total
includes taxes & fees
Mar 4 - Mar 5
Cozy cabin w/private hot tub & game room
Smart TV, fireplace, foosball, books

Cabin in Harpers Ferry

Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly
10.0 out of 10, Exceptional, (5 reviews)
"Very clean, great amenities, comfortable!"
United States
James
The price is ￥23,876
￥77,950 total
includes taxes & fees
Mar 3 - Mar 4
Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly
Dining

Cabin in Harpers Ferry

Log Cabin w/ Hot Tub & Waterfront Patio!
9.6 out of 10, Exceptional, (18 reviews)
"Everything was great! We had a lovely stay."
United States
Beth D.
The price is ￥15,605
￥55,554 total
includes taxes & fees
Mar 2 - Mar 3
Log Cabin w/ Hot Tub & Waterfront Patio!
Terrace/patio

Cottage in Front Royal

"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
10.0 out of 10, Exceptional, (5 reviews)
"My family and I had a wonderful stay! The property and surrounding views are beautiful. The house was very clean and the host was very responsive when I had a question or two to ask. I highly recommend staying here!"
United States
Jay L.
The price is ￥22,449
￥62,974 total
includes taxes & fees
Mar 8 - Mar 9
"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
Outdoor spa tub

Cabin in Linden

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
9.4 out of 10, Exceptional, (13 reviews)
"Fun location near tons of wineries, bowling, trails, and mountain living. Place is really nice with a grill, solo stove, kfantastic kitchen"
United States
Bret L.
The price is ￥19,101
￥53,426 total
includes taxes & fees
Mar 9 - Mar 10
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Terrace/patio

Cabin in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
10.0 out of 10, Exceptional, (2 reviews)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is ￥20,365
￥25,554 total
includes taxes & fees
Mar 23 - Mar 24
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Interior

Cottage in Hamilton

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
9.8 out of 10, Exceptional, (11 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 ￥35,111
￥61,198 total
includes taxes & fees
Mar 2 - Mar 3
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Exterior

Cabin in Front Royal

The Far View Retreat | Hot Tub + Scenic Views
10.0 out of 10, Exceptional, (15 reviews)
"The cabin was spacious and well equipped. The rooms were clean and comfy. The hot tub was clean and refreshing after a long hiking day. Lovd the covered deck for watching sunrises and the deer. I heard a coyote howl early one morning."
United States
Gina H.
The price is ￥28,089
￥71,775 total
includes taxes & fees
Mar 4 - Mar 5
The Far View Retreat | Hot Tub + Scenic Views
Exterior

Cottage in Middleburg

18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (56 reviews)
"Loved out stay! "
United States
Emilee
The price is ￥42,914
￥61,453 total
includes taxes & fees
Mar 2 - Mar 3
18th Century Stone Cottage minutes from historic Middleburg
Terrace/patio

Vacation Home in Front Royal

Mountain View Bungalow in Front Royal
10.0 out of 10, Exceptional, (13 reviews)
"Super cute, super clean and super comfortable!! Close and convenient to Shenandoah NP. Would definitely stay again!"
United States
Brian B.
The price is ￥21,067
￥34,043 total
includes taxes & fees
Mar 2 - Mar 3
Mountain View Bungalow in Front Royal
Outdoor dining

Cabin in Linden

Skyland Hideaway | Mountain Cabin w/ Hot Tub
10.0 out of 10, Exceptional, (15 reviews)
"As described. Enjoyed the cleanliness, hot tub, coziness of the cabin. Host was available if needed. "
United States
Roger M.
The price is ￥25,748
￥66,956 total
includes taxes & fees
Mar 15 - Mar 16
Skyland Hideaway | Mountain Cabin w/ Hot Tub
Interior

Cottage in Leesburg's Old and Historic District

Royal Heritage Home @ Historic Leesburg
9.8 out of 10, Exceptional, (39 reviews)
"Great location, would stay again."
United States
Eric D S.
The price is ￥38,405
￥80,236 total
includes taxes & fees
Mar 5 - Mar 6
Royal Heritage Home @ Historic Leesburg
Property grounds

Chalet in Harpers Ferry

Cozy w/Fire Pit, Grill, Screened Porch & WiFi
10.0 out of 10, Exceptional, (3 reviews)
"The host was very communicative and the place was very clean. "
United States
Christopher M.
The price is ￥24,931
￥47,808 total
includes taxes & fees
Mar 3 - Mar 4
Cozy w/Fire Pit, Grill, Screened Porch & WiFi
TV

Cottage in Front Royal

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
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 ￥23,173
￥34,513 total
includes taxes & fees
Mar 3 - Mar 4
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Dining

Cabin in Harpers Ferry

Cozy Cabin Hidden Away on a Lake!
9.6 out of 10, Exceptional, (44 reviews)
"The house and setting were perfect. We recommend the cabin."
United States
Pat A.
The price is ￥15,605
￥55,554 total
includes taxes & fees
Mar 2 - Mar 3
Cozy Cabin Hidden Away on a Lake!
Interior

Cabin in Linden

Hidden Gem on Hidden Valley Lane
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 ￥31,210
￥70,828 total
includes taxes & fees
Mar 2 - Mar 3
Hidden Gem on Hidden Valley Lane
Smart TV

Apartment in Amissville

Cozy 1BR Apt Minutes From Skyline Drive!!
9.8 out of 10, Exceptional, (42 reviews)
"Cozy and clean. We enjoy the peace and quiet and a great and safe area and neighborhood. "
United States
Theresa S.
The price is ￥18,960
￥35,576 total
includes taxes & fees
Mar 2 - Mar 3
Cozy 1BR Apt Minutes From Skyline Drive!!
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

Home2 Suites by Hilton Leesburg

Home2 Suites by Hilton Leesburg

10/10 Excellent
"The personnel is extremely helpful and polite. The cleanness and space of the room was great"
EDWING 4-night trip
Posted 1 day ago
Home2 Suites by Hilton Leesburg

Find out more about Upperville

Search for holiday rentals in Upperville on Expedia! You can easily find your home rentals, villas, holiday apartments in Upperville using one of the methods below:

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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 View with an Indoor Pool: 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. You can relax into your vacation with a selection of games and a hot tub.

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 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.