Holiday Homes in Upperville

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Upperville holiday homes

Lamontagne Farmhouse a Rural Pristine Setting

Lamontagne Farmhouse a Rural Pristine Setting
Bluemont
10.0 out of 10, Exceptional, (12 reviews)
"We loved our stay at this beautiful tranquil farmhouse. Our two Golden’s enjoyed the outdoor space. Hiking close by, a beautiful drive to visit Middleburg is a must. We highly recommend this charming getaway."
United States
AnneMarie M.
The price is AU$337
includes taxes & fees
5 Feb - 6 Feb
Lamontagne Farmhouse a Rural Pristine Setting

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 AU$454
includes taxes & fees
2 Feb - 3 Feb
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, (13 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 AU$318
includes taxes & fees
1 Feb - 2 Feb
Mountain View Bungalow in Front Royal

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.
The price is AU$587
includes taxes & fees
10 Feb - 11 Feb
Riverview Retreat - Pool, Hot Tub, and Mtn Views!

Historic Bluemont Village Home

Historic Bluemont Village Home
Bluemont
10.0 out of 10, Exceptional, (39 reviews)
"This was one of the best VRBO experiences I’ve had! Communication with the host was exceptional, and the home itself was gorgeous. It’s clear they have put a lot of thought into make this house a perfect getaway — it is beautifully decorated and has all the comforts of home. We will definitely stay here again!"
United States
Mary S.
The price is AU$598
includes taxes & fees
3 Feb - 4 Feb
Historic Bluemont Village Home

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
9.4 out of 10, Exceptional, (3 reviews)
"Property was very clean and accurate of listing description. cell phone service was rough however internet in house was never an issue. House is in good shape. Owner was quick to respond once receiving text message. Email is best way to communicate. you do have a lil drive into town if you need something however that was not an issue with us and the location is what we were looking for. Would 100% stay again if in the area"
United States
Kevin W.
The price is AU$553
includes taxes & fees
18 Feb - 19 Feb
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

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 AU$458
includes taxes & fees
3 Mar - 4 Mar
Newly renovated Farm cottage with Mountain views

The Apple Mountain House

The Apple Mountain House
Front Royal
9.6 out of 10, Exceptional, (10 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is AU$500
includes taxes & fees
4 Feb - 5 Feb
The Apple Mountain House

Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!
Charles Town
9.6 out of 10, Exceptional, (66 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 AU$563
includes taxes & fees
16 Feb - 17 Feb
Terra Alta - Incredible River Views and Hot Tub!

NEW! Ferrystone Lodge: Mountain Retreat w/ Patio & Fireplace

NEW! Ferrystone Lodge: Mountain Retreat w/ Patio & Fireplace
Harpers Ferry
10.0 out of 10, Exceptional, (7 reviews)
The price is AU$492
includes taxes & fees
2 Feb - 3 Feb
NEW! Ferrystone Lodge: Mountain Retreat w/ Patio & Fireplace

Cozy Hidden Cabin 7 Mins To Town With Parking

Cozy Hidden Cabin 7 Mins To Town With Parking
Harpers Ferry
10.0 out of 10, Exceptional, (10 reviews)
"The home was clean and beautifully decorated. "
United States
Preeti r.
The price is AU$520
includes taxes & fees
2 Feb - 3 Feb
Cozy Hidden Cabin 7 Mins To Town With Parking

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.
The price is AU$572
includes taxes & fees
4 Feb - 5 Feb
Big Sunny Family House

Welcome to the Ladybug Retreat!

Welcome to the Ladybug Retreat!
Boyce
10.0 out of 10, Exceptional, (1 review)
"This home is lovely and the host has thought of everything. We will definitely stay here again. "
United States
Catherine A.
The price is AU$565
includes taxes & fees
5 Feb - 6 Feb
Welcome to the Ladybug Retreat!

Mountain Retreat w 2 Living Spaces & Scenic Deck

Mountain Retreat w 2 Living Spaces & Scenic Deck
Harpers Ferry
The price is AU$433
includes taxes & fees
2 Feb - 3 Feb
Mountain Retreat w 2 Living Spaces & Scenic Deck

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
Linden
10.0 out of 10, Exceptional, (22 reviews)
"Very nice stay! A peaceful, quiet little place. Cozy beds! We enjoyed our time. "
United States
Katelyn E.
The price is AU$487
includes taxes & fees
23 Feb - 24 Feb
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

New 3 Bedroom 3 Bath Mountain Retreat

New 3 Bedroom 3 Bath Mountain Retreat
Harpers Ferry
10.0 out of 10, Exceptional, (2 reviews)
"Everything in the listing is true to the home. Description is spot on and the pictures are exactly how we found everything. It is truly a Mountain Retreat. Secluded enough to feel like a true isolated getaway, but also close enough to everything as to not have drive forever to get supplies or sightsee. We had a wonderful time and will definitely stay again if we return. "
United States
Drew W.
The price is AU$523
includes taxes & fees
1 Feb - 2 Feb
New 3 Bedroom 3 Bath Mountain Retreat

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (25 reviews)
"A nice relaxing place to stay in the mountains of WV near many things to do. Check-in and check-out instructions were easy to follow. "
United States
L G.
The price is AU$607
includes taxes & fees
2 Feb - 3 Feb
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

LUX Lakefront King Suites w/Dock, HotTub, Kayaks

LUX Lakefront King Suites w/Dock, HotTub, Kayaks
Shannondale
10.0 out of 10, Exceptional, (1 review)
"The entire house was AMAZING!!! The hosts were fantastic. They sent us activities to do in the area, stocked the house with everything we could possibly need, baked us cookies, and left us refreshments. The house was very clean and had plenty of space and things to do even if you don’t want to go anywhere. Every room has a lake view and each bathroom feels as clean as a hotel!"
United States
Rosalie G.
The price is AU$2,030
includes taxes & fees
8 Feb - 9 Feb
LUX Lakefront King Suites w/Dock, HotTub, Kayaks

Retreat in Historic Downtown Leesburg - Walkable to Everything!

Retreat in Historic Downtown Leesburg - Walkable to Everything!
Leesburg's Old and Historic District
10.0 out of 10, Exceptional, (13 reviews)
"House was in a great location. "
United States
kevin m.
The price is AU$665
includes taxes & fees
3 Feb - 4 Feb
Retreat in Historic Downtown Leesburg - Walkable to Everything!

Mountain cottage w/hot tub & fire pit

Mountain cottage w/hot tub & fire pit
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$454
includes taxes & fees
5 Feb - 6 Feb
Mountain cottage w/hot tub & fire pit
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Upperville Hotel Reviews

Find out more about Upperville

Upperville Holiday Homes information

Number of reviews
315
Accommodation
231 Holiday Homes
Lowest Price
AU$318
Highest Price
AU$2,030