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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Upperville vacation homes

Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (17 reviews)
"We enjoyed our stayed so much! This location is perfect. This property is so clean. "
United States
Nicole Z.
The price is AED 496
AED 797 total
includes taxes & fees
13 Apr - 14 Apr
Mountain View Bungalow in Front Royal
TV, offices

Shenandoah mountain cottage w/hot tub & fire pit

Shenandoah 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 AED 628
AED 1,154 total
includes taxes & fees
14 Apr - 15 Apr
Shenandoah mountain cottage w/hot tub & fire pit
Outdoor dining

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, (24 reviews)
"The house was very nice and the hosts were communicative and provided everything we needed."
United States
Jackie C.
The price is AED 672
AED 1,637 total
includes taxes & fees
12 Apr - 13 Apr
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Property grounds

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 AED 658
AED 1,284 total
includes taxes & fees
14 Apr - 15 Apr
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Interior

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 AED 687
AED 1,496 total
includes taxes & fees
13 Apr - 14 Apr
Stone Cabin on Valley View: Fire Pit + Hot Tub
Smart TV, fireplace

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 AED 448
AED 1,285 total
includes taxes & fees
5 May - 6 May
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Exterior

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 AED 929
AED 1,950 total
includes taxes & fees
12 Apr - 13 Apr
Cozy Cottage - 6 Mins To River, Hiking & Trails - Work From Home Paradise
Property grounds

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 AED 588
AED 1,187 total
includes taxes & fees
14 Apr - 15 Apr
Newly renovated Farm cottage with Mountain views
Property grounds

Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!
Charles Town
9.6 out of 10, Exceptional, (67 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 AED 367
AED 1,464 total
includes taxes & fees
16 Apr - 17 Apr
Terra Alta - Incredible River Views and Hot Tub!
Fridge, oven, stovetop, dishwasher

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

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is AED 591
AED 1,193 total
includes taxes & fees
16 Apr - 17 Apr
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Fridge, microwave, oven, dishwasher

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 AED 367
AED 1,509 total
includes taxes & fees
20 Apr - 21 Apr
Riverview Retreat - Pool, Hot Tub, and Mtn Views!
Terrace/patio

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 AED 453
AED 1,387 total
includes taxes & fees
14 Apr - 15 Apr
The Apple Mountain House
Fridge, microwave, oven, stovetop

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 AED 818
AED 1,777 total
includes taxes & fees
9 Apr - 10 Apr
Quaint Royal Cottage @ Historic Leesburg
Property grounds

A unique mountaintop getaway overlooking Willow Croft Winery.

A unique mountaintop getaway overlooking Willow Croft Winery.
Leesburg
10.0 out of 10, Exceptional, (116 reviews)
"Wonderful home with outstanding hosts! Will hope to stay here every time we visit Leesburg!"
United States
Ethan R.
The price is AED 1,157
AED 2,198 total
includes taxes & fees
15 Apr - 16 Apr
A unique mountaintop getaway overlooking Willow Croft Winery.
TV, fireplace, table tennis, stereo

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 AED 1,980
AED 2,390 total
includes taxes & fees
15 Apr - 16 Apr
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
Terrace/patio

Harpers Ferry Mountain Escape w/ Patio & Fireplace

Harpers Ferry Mountain Escape w/ Patio & Fireplace
Harpers Ferry
10.0 out of 10, Exceptional, (7 reviews)
"Very welcoming host, with clear instructions. Lovely home with a beautiful back patio. Easy to find and close to so many places "
United States
Alex C.
The price is AED 550
AED 1,385 total
includes taxes & fees
13 Apr - 14 Apr
Harpers Ferry Mountain Escape w/ Patio & Fireplace
Exterior

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 AED 727
AED 1,274 total
includes taxes & fees
26 Apr - 27 Apr
Cameron Charmer pristine downtown apt with double master suites
Fridge, microwave, oven, stovetop

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 AED 826
AED 1,888 total
includes taxes & fees
19 Apr - 20 Apr
Spacious Modern Home on Middleburg Horse Farm
Interior

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

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
The price is AED 808
AED 1,709 total
includes taxes & fees
5 May - 6 May
Bluemont home just minutes to wineries, breweries, hiking and more!
Interior

The Rollason River Retreat - Four Bedroom Home with Game Room and Boat Access

The Rollason River Retreat - Four Bedroom Home with Game Room and Boat Access
Front Royal
The Rollason River Retreat - Four Bedroom Home with Game Room and Boat Access
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Clean motel and comfortable room."
Janet 1-night trip
Posted 2 hours ago
Comfort Inn & Suites Winchester

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