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Holiday Homes in Upperville

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Upperville holiday homes

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 NZ$576
includes taxes & fees
30 June - 1 July
Leesburg Hideaway- King Bed + Private Backyard
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 NZ$738
includes taxes & fees
19 July - 20 July
Bluemont home just minutes to wineries, breweries, hiking and more!
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, (5 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 NZ$724
includes taxes & fees
1 July - 2 July
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
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, (28 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is NZ$721
includes taxes & fees
30 June - 1 July
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (31 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 NZ$387
includes taxes & fees
1 July - 2 July
Mountain View Bungalow in Front Royal
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 NZ$578
includes taxes & fees
12 July - 13 July
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
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 NZ$566
includes taxes & fees
7 July - 8 July
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
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 NZ$541
includes taxes & fees
5 July - 6 July
Mountain home w/ hot tub & sunroom
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 NZ$690
includes taxes & fees
30 June - 1 July
Stone Cabin on Valley View: Fire Pit + Hot Tub
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 NZ$772
includes taxes & fees
16 July - 17 July
Terra Alta - Incredible River Views and Hot Tub!
Property grounds

Breathtaking Dome with Spectacular Interior and Exterior in Leesburg, Virginia

Breathtaking Dome with Spectacular Interior and Exterior in Leesburg, Virginia
Leesburg
The price is NZ$569
includes taxes & fees
7 July - 8 July
Breathtaking Dome with Spectacular Interior and Exterior in Leesburg, Virginia
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 NZ$2,035
includes taxes & fees
1 July - 2 July
Buckskin Manor - Historic, Pool, 66 Acre Vineyard
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 NZ$1,039
includes taxes & fees
7 July - 8 July
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
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 NZ$466
includes taxes & fees
7 July - 8 July
Secluded stonehouse in Marshall with walking trails and creek. Pet-friendly!
Fridge, microwave, oven, stovetop

Greek Spa • Private Acreage • Stonefire pizza oven

Greek Spa • Private Acreage • Stonefire pizza oven
Front Royal
2.0 out of 10, (1 review)
"All of the amenities were very dirty. Hot tub and pizza oven look like they are never cleaned and there was a load of dirty dishes in the dishwasher when we arrived. The house interior was fine and comfortable and self check in was easy. However the heavy advertising around the amenities are a bait and switch."
United States
Ben T.
The price is NZ$581
includes taxes & fees
30 June - 1 July
Greek Spa • Private Acreage • Stonefire pizza oven
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, (8 reviews)
"Welcoming host, great place!"
United States
Amanda M.
The price is NZ$773
includes taxes & fees
14 July - 15 July
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
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, (20 reviews)
"Beautiful home and surroundings. Peaceful. Spacious. Lovely. "
United States
Debra D.
The price is NZ$1,106
includes taxes & fees
30 June - 1 July
Spacious Modern Home on Middleburg Horse Farm
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
9.8 out of 10, Exceptional, (6 reviews)
The price is NZ$456
includes taxes & fees
14 July - 15 July
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Fridge, microwave, oven, stovetop

Bend of Brothers’ | Riverfront Cottage Shenandoah

Bend of Brothers’ | Riverfront Cottage Shenandoah
Front Royal
The price is NZ$711
includes taxes & fees
30 June - 1 July
Bend of Brothers’ | Riverfront Cottage Shenandoah
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, (11 reviews)
"Great place to stay!! Very happy with the accommodations "
United States
Amanda E.
The price is NZ$740
includes taxes & fees
7 July - 8 July
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

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent
"Very clean and comfortable hotel. Bathroom was very small, room a good size. A/C was comfortable. Reception pleasant"
Amy 1-night trip
Posted 1 hour ago
Microtel Inn & Suites by Wyndham Winchester

Find out more about Upperville

Upperville Holiday Homes information

Number of reviews
367
Accommodation
241 Holiday Homes
Lowest Price
NZ$387
Highest Price
NZ$2,035