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, (33 reviews)
"Lovely property, really nicely furnished and clean. Brilliant location for lots of places locally and close enough to walk into Leesburg itself to get ice cream!"
United Kingdom
Rachael B.
The price is €265
includes taxes & fees
23 Mar - 24 Mar
Leesburg Hideaway- King Bed + Private Backyard

Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.

Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.
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 €257
includes taxes & fees
23 Mar - 24 Mar
Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.

Shenandoah mountain cottage w/ hot tub & lake

Shenandoah mountain cottage w/ hot tub & lake
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 €273
includes taxes & fees
19 Mar - 20 Mar
Shenandoah mountain cottage w/ hot tub & lake

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is €281
includes taxes & fees
22 Mar - 23 Mar
Newly renovated Farm cottage with Mountain views

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

Riverview Retreat - Pool, Hot Tub, and Mtn Views!
Harpers Ferry
10.0 out of 10, Exceptional, (1 review)
"We had a great time at Riverview Retreat! The house was perfect for our group and offered beautiful views. We especially loved the fireplace and all of the amenities they had available. The hot tub code was missing from the manual so we weren't able to use it on our first night and the spiral staircase was pretty intimidating for the weather we had. Heed the warnings about needing four wheel drive in the winter for the driveway. I was thankful there wasn't snow as it would have been scary to...
United States
Stacy H.
Riverview Retreat - Pool, Hot Tub, and Mtn Views!

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (16 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 €192
includes taxes & fees
22 Mar - 23 Mar
Mountain View Bungalow in Front Royal

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, (22 reviews)
"We had a great stay! The house was clean, nicely decorated and had every amenity we needed! "
United States
Julie H.
The price is €381
includes taxes & fees
19 Mar - 20 Mar
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

Indigo Blue modern open vibe on tree lined street

Indigo Blue modern open vibe on tree lined street
Winchester Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Perfect for our needs for our daughter’s graduation!"
United States
Chris and Michelle P.
The price is €345
includes taxes & fees
22 Mar - 23 Mar
Indigo Blue modern open vibe on tree lined street

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 €336
includes taxes & fees
22 Mar - 23 Mar
The Apple Mountain House

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 €474
includes taxes & fees
19 Mar - 20 Mar
The Cottage on Royal - Historic Leesburg Home

Dog-Friendly Cottage w Playground, Grill & Games

Dog-Friendly Cottage w Playground, Grill & Games
Middletown
9.6 out of 10, Exceptional, (17 reviews)
"Clean cute house, exactly as described. Close to Shenandoah national park and skyline drive. Hosts very communicative "
United States
Corrin D.
The price is €250
includes taxes & fees
22 Mar - 23 Mar
Dog-Friendly Cottage w Playground, Grill & Games

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)
"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"
United States
Vinod B.
The price is €287
includes taxes & fees
25 Mar - 26 Mar
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

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

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is €289
includes taxes & fees
22 Mar - 23 Mar
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Cozy Cottage - 6 Mins To River, Hiking & Trails - Work From Home Paradise

Cozy Cottage - 6 Mins To River, Hiking & Trails - Work From Home Paradise
Harpers Ferry
10.0 out of 10, Exceptional, (10 reviews)
"The home was clean and beautifully decorated. "
United States
Preeti r.
The price is €379
includes taxes & fees
19 Mar - 20 Mar
Cozy Cottage - 6 Mins To River, Hiking & Trails - Work From Home Paradise

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 €348
includes taxes & fees
19 Mar - 20 Mar
Stone Cabin on Valley View: Fire Pit + Hot Tub

Spring Haven Escape w/ Patio & Fireplace

Spring Haven Escape w/ Patio & Fireplace
Harpers Ferry
10.0 out of 10, Exceptional, (7 reviews)
"The house was perfect. Every detail was thought through and it was even decorated beautifully for Christmas. We were very comfortable and all amenities were available as advertised. Host were extremely responsive and thoughtful Appreciated the recommendations as well. Highly recommend and look forward to our next day there."
United States
Gina B.
The price is €333
includes taxes & fees
19 Mar - 20 Mar
Spring Haven Escape w/ Patio & Fireplace

Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (17 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 €434
includes taxes & fees
26 Mar - 27 Mar
Spacious Modern Home on Middleburg Horse Farm

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)
"Our family stayed for Thanksgiving week while visiting other family in The Plains. This spot for us all perfectly. Kyle was super nice and responsive . Everything was easy & pleasant. Loved being surrounded by woods. "
United States
Nina M.
The price is €543
includes taxes & fees
23 Mar - 24 Mar
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

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, (69 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 €411
includes taxes & fees
22 Mar - 23 Mar
Cottage on King | Charming Historic Leesburg Home

Big Sunny Family House

Big Sunny Family House
Front Royal
10.0 out of 10, Exceptional, (42 reviews)
"Wonderful house and town! Loved every minute of our trip! "
United States
MaryAnn G.
Big Sunny Family House
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
344
Accommodation
231 Holiday Homes
Lowest Price
€192
Highest Price
€543