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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Upperville holiday homes

Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (26 reviews)
"We had a wonderful time and the amenities were perfect!"
United States
Douglas S.
The price is £166
includes taxes & fees
4 Jun - 5 Jun
Mountain View Bungalow in Front Royal
Outdoor dining

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, (5 reviews)
The price is £205
includes taxes & fees
9 Jun - 10 Jun
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Terrace/patio

Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.8 out of 10, Exceptional, (11 reviews)
"We had a great stay "
United States
Lauren O.
The price is £297
includes taxes & fees
4 Jun - 5 Jun
Huckleberry Hills | Hot Tub & Fire Pit & Dogs
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 £247
includes taxes & fees
11 Jun - 12 Jun
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Fridge, microwave, oven, stovetop

super cosy cottage with high speed internet!

super cosy cottage with high speed internet!
Middleburg
9.4 out of 10, Exceptional, (14 reviews)
"Lovely setting in horse country with nice amenities "
United States
Christopher v.
The price is £242
includes taxes & fees
8 Jun - 9 Jun
super cosy cottage with high speed internet!
Property grounds

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 £315
includes taxes & fees
9 Jun - 10 Jun
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
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 £246
includes taxes & fees
8 Jun - 9 Jun
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Living area

Still Meadow Farm

Still Meadow Farm
Purcellville
10.0 out of 10, Exceptional, (2 reviews)
"Still Meadow is a beautiful place to stay, super clean, We would definitely recommend. Host was responsive and accommodating."
United States
Jodie J.
The price is £981
includes taxes & fees
14 Jun - 15 Jun
Still Meadow 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 £272
includes taxes & fees
9 Jun - 10 Jun
Bluemont home just minutes to wineries, breweries, hiking and more!
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, (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 £428
includes taxes & fees
21 Jun - 22 Jun
Terra Alta - Incredible River Views and Hot Tub!
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, (14 reviews)
"Beautiful scenery! Beautiful home! Wonderful hosts!"
United States
Brian S.
The price is £271
includes taxes & fees
10 Jun - 11 Jun
Stone Cabin on Valley View: Fire Pit + Hot Tub
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, (12 reviews)
"Great location in a great town!"
United States
Gigi D.
The price is £388
includes taxes & fees
4 Jun - 5 Jun
Quaint Royal Cottage @ Historic Leesburg
Outdoor dining

Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge

Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge
Shannondale
10.0 out of 10, Exceptional, (3 reviews)
"My family and ai had an amazing stay at Deb and Alex’s rental in WV! It was easy to check-in, very clean, and had convenient amenities! Would definitely consider staying with them again!"
United States
Anonymous traveller
The price is £402
includes taxes & fees
9 Jun - 10 Jun
Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge
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, (27 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is £333
includes taxes & fees
17 Jun - 18 Jun
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Smart TV, fireplace, DVD player, books

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.
The price is £302
includes taxes & fees
15 Jun - 16 Jun
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Property grounds

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (43 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is £229
includes taxes & fees
14 Jun - 15 Jun
Newly renovated Farm cottage with Mountain views
3 bedrooms, desk, iron/ironing board, travel cot

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, (12 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 £301
includes taxes & fees
4 Jun - 5 Jun
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Property grounds

The Blue Jay | New House in the Woods w/ Hot Tub

The Blue Jay | New House in the Woods w/ Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (2 reviews)
"Great place. Very well stocked house everything you need Great response from host. Very nice place. Road is a little rough as explained in listing "
United States
Brett D.
The price is £269
includes taxes & fees
17 Jun - 18 Jun
The Blue Jay | New House in the Woods w/ Hot Tub
Exterior

Buckskin Manor - Historic, Pool, 66 Acre Vineyard

Buckskin Manor - Historic, Pool, 66 Acre Vineyard
Purcellville
9.0 out of 10, Wonderful, (23 reviews)
"Beautiful home on absolutely magnificent propertyTastefully decorated with lovely pieces of furniture and whimsical touchesLots of different areas for eating, reading and relaxingThe pool was fantasticGreat choice for a memorable family vacation! "
United States
Chana T.
The price is £813
includes taxes & fees
10 Jun - 11 Jun
Buckskin Manor - Historic, Pool, 66 Acre Vineyard
Interior

A peaceful, forest retreat with stunning views near historic Harpers Ferry.

A peaceful, forest retreat with stunning views near historic Harpers Ferry.
Harpers Ferry
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay!! Very happy with the accommodations "
United States
Amanda E.
The price is £294
includes taxes & fees
8 Jun - 9 Jun
A peaceful, forest retreat with stunning views near historic Harpers Ferry.
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

4/10 Poor
"Wireless spotty, tv didn’t work well"
Bonnie 1-night trip
Posted 1 hour ago
Comfort Inn & Suites Winchester

Find out more about Upperville

Upperville Holiday Homes information

Number of reviews
366
Accommodation
238 Holiday Homes
Lowest Price
£166
Highest Price
£981