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Holiday Homes in Upperville

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Check prices for these dates

In two weeks
3 July - 5 July
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Upperville holiday homes

Fridge, microwave, oven, stovetop

Greek Spa • Private Acreage • Stonefire pizza oven

Greek Spa • Private Acreage • Stonefire pizza oven
Front Royal
The price is AU$463
includes taxes & fees
23 June - 24 June
Greek Spa • Private Acreage • Stonefire pizza oven
Smart TV, books, computer monitors

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (35 reviews)
"Adorable, comfy, private & well appointed. Well cleared of snow for our arrival after a difficult snow/ice storm. Comfortable mattress was a bonus. We enjoyed our stay! "
United States
Amy M.
The price is AU$528
includes taxes & fees
22 June - 23 June
Leesburg Hideaway- King Bed + Private Backyard
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, (3 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 AU$519
includes taxes & fees
21 June - 22 June
The Blue Jay | New House in the Woods w/ Hot Tub
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 AU$495
includes taxes & fees
23 June - 24 June
Bluemont home just minutes to wineries, breweries, hiking and more!
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 AU$467
includes taxes & fees
18 June - 19 June
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
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 AU$596
includes taxes & fees
24 June - 25 June
Huckleberry Hills | Hot Tub & Fire Pit & Dogs
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, (71 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$633
includes taxes & fees
1 July - 2 July
Terra Alta - Incredible River Views and 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 AU$503
includes taxes & fees
24 June - 25 June
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
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 AU$501
includes taxes & fees
20 June - 21 June
super cosy cottage with high speed internet!
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (27 reviews)
"We had a great stay! The house is cozy and just perfect for a private get away. The hosts were very communicative and wonderful, we will be back! "
United States
Virginia A.
The price is AU$317
includes taxes & fees
25 June - 26 June
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 AU$487
includes taxes & fees
28 June - 29 June
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
TV, offices

Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
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$455
includes taxes & fees
21 June - 22 June
Mountain home w/ hot tub & sunroom
Terrace/patio

Harpers Ferry: Charming Home w/ Patio & Fireplace

Harpers Ferry: Charming Home w/ Patio & Fireplace
Harpers Ferry
10.0 out of 10, Exceptional, (8 reviews)
"Great location and amenities, super clean and the smores were a nice bonus "
United States
William S.
The price is AU$645
includes taxes & fees
29 June - 30 June
Harpers Ferry: Charming Home w/ Patio & Fireplace
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)
The price is AU$647
includes taxes & fees
14 July - 15 July
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Property grounds

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (45 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is AU$432
includes taxes & fees
24 June - 25 June
Newly renovated Farm cottage with Mountain views
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, (13 reviews)
"Beautiful scenery! Beautiful home! Wonderful hosts!"
United States
Brian S.
The price is AU$538
includes taxes & fees
23 June - 24 June
Stone Cabin on Valley View: Fire Pit + Hot Tub
Interior

Secluded stonehouse in Marshall with walking trails and creek. Pet-friendly!

Secluded stonehouse in Marshall with walking trails and creek. Pet-friendly!
Marshall
10.0 out of 10, Exceptional, (3 reviews)
"My two pups and I enjoyed a wonderful two night stay at the cottage! Great location with walking trails on-site, and plenty of restaurants within a 15-20min drive. The porch was perfect for an evening glass of wine and a book. I'd be happy to come back again."
United States
Shannon S.
The price is AU$342
includes taxes & fees
6 July - 7 July
Secluded stonehouse in Marshall with walking trails and creek. Pet-friendly!
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
7.4 out of 10, Good, (28 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$459
includes taxes & fees
22 June - 23 June
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Fridge, microwave, oven, stovetop

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Harpers Ferry
9.8 out of 10, Exceptional, (112 reviews)
"The house was as advertised and served as a great location for our retreat! We had a freak plumbing emergency, and the host fixed it within literally an hour. "
United States
Connie V.
The price is AU$861
includes taxes & fees
7 July - 8 July
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Exterior

Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.6 out of 10, Exceptional, (8 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is AU$492
includes taxes & fees
29 June - 30 June
Cameron Charmer pristine downtown apt with double master suites
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

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"Excellent stay. The rooms were very clean, delicious breakfast and friendly staff"
Chantelle 1-night trip
Posted 3 hours ago
TRU By Hilton Winchester

Find out more about Upperville

Upperville Holiday Homes information

Number of reviews
366
Accommodation
238 Holiday Homes
Lowest Price
AU$317
Highest Price
AU$861