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Our top choices for Upperville vacation homes

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Harpers Ferry
7.6 out of 10, Good, (27 reviews)
"The inside was well done and clean. Even though the neighbors are close, they were quiet. My husband and I were able to relax in a comfortable setting."
United States
Melissa H.
The price is AED 519
AED 1,105 total
includes taxes & fees
22 Apr - 23 Apr
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Harpers Ferry
10.0 out of 10, Exceptional, (25 reviews)
"The house was very nice and the hosts were communicative and provided everything we needed."
United States
Jackie C.
The price is AED 672
AED 1,637 total
includes taxes & fees
22 Apr - 23 Apr
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

Stone Cabin on Valley View: Fire Pit + Hot Tub

Stone Cabin on Valley View: Fire Pit + Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful scenery! Beautiful home! Wonderful hosts!"
United States
Brian S.
The price is AED 606
AED 1,396 total
includes taxes & fees
27 Apr - 28 Apr
Stone Cabin on Valley View: Fire Pit + Hot Tub

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (21 reviews)
"We enjoyed our stayed so much! This location is perfect. This property is so clean. "
United States
Nicole Z.
The price is AED 496
AED 814 total
includes taxes & fees
22 Apr - 23 Apr
Mountain View Bungalow in Front Royal

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is AED 591
AED 1,200 total
includes taxes & fees
22 Apr - 23 Apr
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (40 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is AED 588
AED 1,191 total
includes taxes & fees
26 Apr - 27 Apr
Newly renovated Farm cottage with Mountain views

The Apple Mountain House

The Apple Mountain House
Front Royal
9.8 out of 10, Exceptional, (11 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is AED 766
AED 1,776 total
includes taxes & fees
12 May - 13 May
The Apple Mountain House

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, (70 reviews)
"the cottage had everything we needed. "
United States
christa S.
The price is AED 888
AED 1,630 total
includes taxes & fees
22 Apr - 23 Apr
Cottage on King | Charming Historic Leesburg Home

A unique mountaintop getaway overlooking Willow Croft Winery.

A unique mountaintop getaway overlooking Willow Croft Winery.
Leesburg
10.0 out of 10, Exceptional, (116 reviews)
"Wonderful home with outstanding hosts! Will hope to stay here every time we visit Leesburg!"
United States
Ethan R.
The price is AED 1,818
AED 3,057 total
includes taxes & fees
29 Apr - 30 Apr
A unique mountaintop getaway overlooking Willow Croft Winery.

Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.4 out of 10, Exceptional, (6 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is AED 727
AED 1,240 total
includes taxes & fees
26 Apr - 27 Apr
Cameron Charmer pristine downtown apt with double master suites

Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!
Charles Town
9.6 out of 10, Exceptional, (69 reviews)
"Nice quiet view, able to sit on deck for hours and talk. Close to restaurants, and stores. Had a great stay."
United States
Paul M.
Terra Alta - Incredible River Views and Hot Tub!

Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
Front Royal
9.0 out of 10, Wonderful, (31 reviews)
"The house itself was clean, the beds are comfortable, and it is in a nice, quiet, and private location. The property manager was very pleasant and responsed to any questions or concerns quickly. "
United States
Elissa S.
The price is AED 703
AED 1,247 total
includes taxes & fees
26 Apr - 27 Apr
Mountain home w/ hot tub & sunroom

Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (18 reviews)
"We loved the huge kitchen and family room, and the location in Virginia horse country was amazing!"
United States
STAN P.
The price is AED 804
AED 1,876 total
includes taxes & fees
22 Apr - 23 Apr
Spacious Modern Home on Middleburg Horse Farm

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (7 reviews)
"Welcoming host, great place!"
United States
Amanda M.
The price is AED 562
AED 1,443 total
includes taxes & fees
28 Apr - 29 Apr
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

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 AED 803
AED 1,768 total
includes taxes & fees
23 Apr - 24 Apr
Quaint Royal Cottage @ Historic Leesburg

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
Linden
10.0 out of 10, Exceptional, (26 reviews)
"Very nice stay! A peaceful, quiet little place. Cozy beds! We enjoyed our time. "
United States
Katelyn E.
The price is AED 695
AED 1,443 total
includes taxes & fees
5 May - 6 May
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

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 AED 716
AED 1,424 total
includes taxes & fees
20 May - 21 May
Leesburg Hideaway- King Bed + Private Backyard

Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country

Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country
Marshall
9.8 out of 10, Exceptional, (29 reviews)
"Everything was great "
United States
James A.
The price is AED 1,906
AED 2,300 total
includes taxes & fees
22 Apr - 23 Apr
Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country

Harpers Ferry Mountain Escape w/ Patio & Fireplace

Harpers Ferry Mountain Escape w/ Patio & Fireplace
Harpers Ferry
10.0 out of 10, Exceptional, (7 reviews)
"Great location and amenities, super clean and the smores were a nice bonus "
United States
William S.
The price is AED 692
AED 1,559 total
includes taxes & fees
22 Apr - 23 Apr
Harpers Ferry Mountain Escape w/ Patio & Fireplace

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Harpers Ferry
10.0 out of 10, Exceptional, (9 reviews)
"Perfect place to spend a few nights with our two dogs. Very clean, great amenities, and beautifully decorated. Highly recommend!! "
United States
Megan L.
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
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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