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)
"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 AU$424
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 AU$418
includes taxes & fees
4 May - 5 May
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

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 AU$458
includes taxes & fees
5 May - 6 May
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, (24 reviews)
"We enjoyed our stayed so much! This location is perfect. This property is so clean. "
United States
Nicole Z.
The price is AU$308
includes taxes & fees
7 May - 8 May
Mountain View Bungalow in Front Royal

Cozy cottage w/hot tub & lake, pet-friendly

Cozy cottage w/hot tub & lake, pet-friendly
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 AU$473
includes taxes & fees
4 May - 5 May
Cozy cottage w/hot tub & lake, pet-friendly

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 AU$549
includes taxes & fees
4 May - 5 May
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 AU$524
includes taxes & fees
4 May - 5 May
Stone Cabin on Valley View: Fire Pit + Hot Tub

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 AU$422
includes taxes & fees
5 May - 6 May
Newly renovated Farm cottage with Mountain views

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 AU$668
includes taxes & fees
5 May - 6 May
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)
"Lovely home and great view. Host communication was fabulous. The welcome snacks, wine, and toiletries were very sweet. "
United States
Kathryn B.
The price is AU$542
includes taxes & fees
5 May - 6 May
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

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

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is AU$458
includes taxes & fees
4 May - 5 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 AU$484
includes taxes & fees
4 May - 5 May
Cameron Charmer pristine downtown apt with double master suites

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 AU$560
includes taxes & fees
11 May - 12 May
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.6 out of 10, Exceptional, (10 reviews)
"The house was a great location for what we were lookin for, the kids loved the hot Tub and being able to explore"
United States
Bryan S.
The price is AU$556
includes taxes & fees
6 May - 7 May
Huckleberry Hills | Hot Tub & Fire Pit & Dogs

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 AU$602
includes taxes & fees
5 May - 6 May
Cottage on King | Charming Historic Leesburg Home

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 AU$808
includes taxes & fees
5 May - 6 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 AU$713
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 AU$532
includes taxes & fees
1 June - 2 June
Bluemont home just minutes to wineries, breweries, hiking and more!

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

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (105 reviews)
"The house was beyond expectations."
United States
Eddie J.
The price is AU$727
includes taxes & fees
15 May - 16 May
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

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, (19 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 AU$671
includes taxes & fees
4 May - 5 May
Retreat in Historic Downtown Leesburg - Walkable to Everything!
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
421
Accommodation
232 Holiday Homes
Lowest Price
AU$308
Highest Price
AU$808