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Our top choices for Upperville vacation homes

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 ¥19,413
¥56,149 total
includes taxes & fees
May 21 - May 22
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (25 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 ¥21,474
¥34,879 total
includes taxes & fees
May 27 - May 28
Mountain View Bungalow in Front Royal

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 ¥14,316
¥63,370 total
includes taxes & fees
May 25 - May 26
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

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 ¥26,771
¥52,680 total
includes taxes & fees
Jun 14 - Jun 15
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

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 ¥27,964
¥50,945 total
includes taxes & fees
Jun 1 - Jun 2
Mountain home w/ hot tub & sunroom

Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!
Charles Town
9.6 out of 10, Exceptional, (70 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 ¥38,813
¥96,882 total
includes taxes & fees
Jun 7 - Jun 8
Terra Alta - Incredible River Views and Hot Tub!

super cosy cottage with high speed internet!

super cosy cottage with high speed internet!
Middleburg
9.6 out of 10, Exceptional, (13 reviews)
"Lovely setting in horse country with nice amenities "
United States
Christopher v.
The price is ¥31,814
¥55,854 total
includes taxes & fees
Jun 13 - Jun 14
super cosy cottage with high speed internet!

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, (26 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is ¥41,613
¥83,364 total
includes taxes & fees
May 22 - May 23
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

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

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is ¥25,591
¥52,156 total
includes taxes & fees
May 21 - May 22
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

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 ¥24,497
¥58,853 total
includes taxes & fees
Jun 9 - Jun 10
Stone Cabin on Valley View: Fire Pit + Hot Tub

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 ¥41,040
¥88,495 total
includes taxes & fees
May 26 - May 27
Spacious Modern Home on Middleburg Horse Farm

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

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
The price is ¥21,793
¥57,539 total
includes taxes & fees
May 26 - May 27
Bluemont home just minutes to wineries, breweries, hiking and more!

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, (71 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 ¥31,098
¥61,010 total
includes taxes & fees
May 27 - May 28
Cottage on King | Charming Historic Leesburg Home

Riverview Retreat - Pool, Hot Tub, and Mtn Views!

Riverview Retreat - Pool, Hot Tub, and Mtn Views!
Harpers Ferry
10.0 out of 10, Exceptional, (4 reviews)
"Had a fantastic time and everything was great! Highly recommend this spot for a vacation if you’re headed for Harper’s ferry."
United States
James A.
The price is ¥43,267
¥105,937 total
includes taxes & fees
May 31 - Jun 1
Riverview Retreat - Pool, Hot Tub, and Mtn Views!

Retreat in Historic Downtown Leesburg - Walkable to Everything!

Retreat in Historic Downtown Leesburg - Walkable to Everything!
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (20 reviews)
"Adorable house, amazing location, clean, and a super comfortable couch. We loved it and would definitely stay again!!"
United States
Dawn W.
The price is ¥32,778
¥73,548 total
includes taxes & fees
May 21 - May 22
Retreat in Historic Downtown Leesburg - Walkable to Everything!

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 ¥22,872
¥48,177 total
includes taxes & fees
Jun 1 - Jun 2
Newly renovated Farm cottage with Mountain views

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, (109 reviews)
"Laura was extremely helpful as we sorted out what we needed. Amazing location near Harpers Ferry and tons of fun stuff to do right there within shouting distance of the property."
United States
Steve Y.
The price is ¥23,145
¥84,527 total
includes taxes & fees
May 25 - May 26
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

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 ¥31,496
¥56,050 total
includes taxes & fees
May 21 - May 22
Cameron Charmer pristine downtown apt with double master suites

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, (10 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 ¥24,179
¥64,681 total
includes taxes & fees
May 21 - May 22
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.6 out of 10, Exceptional, (10 reviews)
"We had a great stay "
United States
Lauren O.
The price is ¥15,907
¥64,608 total
includes taxes & fees
May 25 - May 26
Huckleberry Hills | Hot Tub & Fire Pit & Dogs
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

Upperville Vacation Homes information

Number of reviews
375
Accommodation
238 Vacation Homes
Lowest Price
¥34,879
Highest Price
¥105,937