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Our top choices for Upperville vacation homes

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (34 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 496
AED 1,119 total
includes taxes & fees
6 May - 7 May
Leesburg Hideaway- King Bed + Private Backyard

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 658
AED 1,284 total
includes taxes & fees
11 May - 12 May
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)
"Host was helpful and everything was wonderful."
United States
Karen
The price is AED 538
AED 1,467 total
includes taxes & fees
6 May - 7 May
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (24 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 809 total
includes taxes & fees
6 May - 7 May
Mountain View Bungalow in Front Royal

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 642
AED 1,440 total
includes taxes & fees
12 May - 13 May
Stone Cabin on Valley View: Fire Pit + Hot Tub

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 1,204 total
includes taxes & fees
6 May - 7 May
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

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 1,278 total
includes taxes & fees
10 May - 11 May
Cameron Charmer pristine downtown apt with double master suites

Cozy cottage w/hot tub & lake access

Cozy cottage w/hot tub & lake access
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
10 May - 11 May
Cozy cottage w/hot tub & lake access

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Harpers Ferry
9.6 out of 10, Exceptional, (4 reviews)
"House was beautiful and fully equipped for our stay. The host was very communicative and we really enjoyed our time here. If in the area again would definitely stay here. "
United States
Maeve K.
The price is AED 367
AED 1,501 total
includes taxes & fees
7 May - 8 May
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

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 401
AED 1,255 total
includes taxes & fees
19 May - 20 May
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

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.
The price is AED 367
AED 1,500 total
includes taxes & fees
18 May - 19 May
Terra Alta - Incredible River Views and Hot Tub!

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, (30 reviews)
"Everything was great "
United States
James A.
The price is AED 1,759
AED 2,123 total
includes taxes & fees
6 May - 7 May
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

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 AED 1,065
AED 2,094 total
includes taxes & fees
6 May - 7 May
The Cottage on Royal - Historic Leesburg Home

Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
The price is AED 808
AED 1,705 total
includes taxes & fees
11 May - 12 May
Bluemont home just minutes to wineries, breweries, hiking and more!

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 529
AED 1,126 total
includes taxes & fees
11 May - 12 May
Newly renovated Farm cottage with Mountain views

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.
The price is AED 541
AED 1,470 total
includes taxes & fees
6 May - 7 May
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

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)
"Great location and very comfortable house. Beautiful place to stay, we loved sitting on the porch in the morning with coffee"
United States
Fern
The price is AED 870
AED 1,626 total
includes taxes & fees
11 May - 12 May
Cottage on King | Charming Historic Leesburg Home

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (106 reviews)
"The house was beyond expectations."
United States
Eddie J.
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (19 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 856
AED 1,939 total
includes taxes & fees
18 May - 19 May
Spacious Modern Home on Middleburg Horse Farm

A peaceful, forest retreat with stunning views near historic Harpers Ferry.

A peaceful, forest retreat with stunning views near historic Harpers Ferry.
Harpers Ferry
9.8 out of 10, Exceptional, (7 reviews)
"Great place to stay!! Very happy with the accommodations "
United States
Amanda E.
The price is AED 661
AED 1,407 total
includes taxes & fees
6 May - 7 May
A peaceful, forest retreat with stunning views near historic Harpers Ferry.
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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