Holiday Homes in Upperville

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Our top choices for Upperville holiday homes

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (34 reviews)
"Adorable, comfy, private & well appointed. Well cleared of snow for our arrival after a difficult snow/ice storm. Comfortable mattress was a bonus. We enjoyed our stay! "
United States
Amy M.
The price is NZ$539
includes taxes & fees
20 May - 21 May
Leesburg Hideaway- King Bed + Private Backyard

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 NZ$587
includes taxes & fees
19 May - 20 May
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

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

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (107 reviews)
"The house was beyond expectations."
United States
Eddie J.
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

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 NZ$603
includes taxes & fees
17 May - 18 May
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, (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 NZ$366
includes taxes & fees
26 May - 27 May
Mountain View Bungalow in Front Royal

Cozy cabin w/hot tub & fire pit, lake access

Cozy cabin w/hot tub & fire pit, 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 NZ$539
includes taxes & fees
1 June - 2 June
Cozy cabin w/hot tub & fire pit, lake access

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 NZ$489
includes taxes & fees
1 June - 2 June
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

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 NZ$511
includes taxes & fees
18 May - 19 May
Newly renovated Farm cottage with Mountain views

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 NZ$716
includes taxes & fees
27 May - 28 May
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

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 NZ$961
includes taxes & fees
31 May - 1 June
Terra Alta - Incredible River Views and Hot Tub!

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 NZ$580
includes taxes & fees
17 May - 18 May
Cameron Charmer pristine downtown apt with double master suites

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 NZ$885
includes taxes & fees
18 May - 19 May
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 NZ$639
includes taxes & fees
2 June - 3 June
Bluemont home just minutes to wineries, breweries, hiking and more!

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

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is NZ$551
includes taxes & fees
20 May - 21 May
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

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 NZ$1,119
includes taxes & fees
27 May - 28 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

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
9.6 out of 10, Exceptional, (4 reviews)
"A wonderfully equipped home in a lovely location. Everything you could ever need was on hand. "
United States
alison m.
The price is NZ$487
includes taxes & fees
20 May - 21 May
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

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, (108 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 NZ$943
includes taxes & fees
8 June - 9 June
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

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 NZ$741
includes taxes & fees
18 May - 19 May
Retreat in Historic Downtown Leesburg - Walkable to Everything!

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 NZ$705
includes taxes & fees
17 May - 18 May
Cottage on King | Charming Historic Leesburg Home

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 NZ$688
includes taxes & fees
18 May - 19 May
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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Top Upperville Hotel Reviews

Find out more about Upperville

Upperville Holiday Homes information

Number of reviews
566
Accommodation
241 Holiday Homes
Lowest Price
NZ$366
Highest Price
NZ$1,119