Holiday Homes in Upperville

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Upperville

Cottage on King | Charming Historic Leesburg Home
Terrace/patio

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (54)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is NZ$476
includes taxes & fees
9 Sept - 10 Sept
Cottage on King | Charming Historic Leesburg Home
Modern Country House on the Shenandoah River
Property grounds

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (37)
"The views are beautiful and the house was the perfect size for a group of 7 friends. We had a great time!"
Modern Country House on the Shenandoah River
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (98)
"This home was absolutely fantastic! Very clean, very close to all things. We had a fantastic time."
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Exterior

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

10.0 out of 10, Exceptional, (3)
"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"
The price is NZ$568
includes taxes & fees
8 Sept - 9 Sept
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
A unique mountaintop getaway overlooking Willow Croft Winery.
Terrace/patio

A unique mountaintop getaway overlooking Willow Croft Winery.

10.0 out of 10, Exceptional, (103)
"The house was beautiful, fully stocked, close to home and vineyards. It surpassed our expectations! Can’t wait to again. "
The price is NZ$1,019
includes taxes & fees
19 Aug - 20 Aug
A unique mountaintop getaway overlooking Willow Croft Winery.
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Property grounds

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

8.8 out of 10, Excellent, (6)
"Four family members stayed for a four day weekend. The place was spotless when we arrived and all amenities are as described. The location is perfect for visiting Harpers Ferry, Shepherdstown, and Antietam. We had wonderful time."
The price is NZ$861
includes taxes & fees
17 Aug - 18 Aug
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Mountain View Bungalow in Front Royal
Fridge, microwave, oven, stovetop

Mountain View Bungalow in Front Royal

"Excelente propiedad "
The price is NZ$391
includes taxes & fees
8 Sept - 9 Sept
Mountain View Bungalow in Front Royal
Breathtaking View with an Indoor Pool
Outdoor dining

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (257)
"We really enjoyed our stay at Bear Chase Manor! Amazing property, great pool, in a beautiful area. We are already discussing possible future visits! "
Breathtaking View with an Indoor Pool
Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing
Outdoor dining

Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing

10.0 out of 10, Exceptional, (2)
"Easy check-in, excellent communication. Home was very clean with quality furnishings and bedding. Lots of thoughtful touches and extras. Located along Shenandoah River makes it picturesque."
Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Terrace/patio

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

10.0 out of 10, Exceptional, (13)
"We appreciate everything from the discrete location,hot tub and many accommodations. What a PERFECT home to stay away from home while we explored the trails and history of the surrounding area. Great eats and trails only minutes away! "
The price is NZ$728
includes taxes & fees
17 Aug - 18 Aug
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Terrace/patio

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

10.0 out of 10, Exceptional, (15)
"The house is well maintained and furnished, and the outdoor space is lovely. We had a great weekend in Leesburg and would come again. "
The price is NZ$630
includes taxes & fees
18 Aug - 19 Aug
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Rural Home, Hot Tub, Campfire, Hardwood Floors
Exterior

Rural Home, Hot Tub, Campfire, Hardwood Floors

9.4 out of 10, Exceptional, (76)
"This was a perfect location for our stay. "
Rural Home, Hot Tub, Campfire, Hardwood Floors
Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area
Property grounds

Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area

9.8 out of 10, Exceptional, (58)
"Beautiful property and grounds. Setting was quiet and peaceful. Would stay again."
Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area
Linden Family Home w/ Yard < 5 Mi to Wineries!
TV, books

Linden Family Home w/ Yard < 5 Mi to Wineries!

2.0 star property
8.6 out of 10, Excellent, (12)
"Great place to stay on a nice mountain my family and dogs loved itMike was great and answered any questions we had will definitely book again in the future"
Linden Family Home w/ Yard < 5 Mi to Wineries!
Modern Mountain Retreat w/ Deck + Hot Tub!
Fridge, microwave, stovetop, dishwasher

Modern Mountain Retreat w/ Deck + Hot Tub!

9.8 out of 10, Exceptional, (74)
"Very comfortable and spacious place with all the comforts of home. We wanted to get away and just relax for a few days and this was perfect!"
Modern Mountain Retreat w/ Deck + Hot Tub!
Terra Alta - Incredible River Views and Hot Tub!
Outdoor spa tub

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (57)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
The price is NZ$679
includes taxes & fees
28 Aug - 29 Aug
Terra Alta - Incredible River Views and Hot Tub!
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Fridge, microwave, oven, stovetop

Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly

10.0 out of 10, Exceptional, (45)
"The home is super clean and well maintained! "
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Terrace/patio

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

9.8 out of 10, Exceptional, (57)
"This is a great place for a large group or family. Lots of beds. Large table for dining. Great backyard for running"
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Property grounds

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

9.6 out of 10, Exceptional, (95)
"Great find for a girls trip…house is close to lots of different activities and very easy to get to. Perfect place to a weekend getaway!"
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Where Charming Local History Meets Modern Comfort ~ Historic Fauquier County, VA
Outdoor dining

Where Charming Local History Meets Modern Comfort ~ Historic Fauquier County, VA

10.0 out of 10, Exceptional, (68)
"Communication with the host was excellent and an early check in was incredibly helpful - the house served its purpose exactly as expected - hosting friends for the weekend with easy access to the countryside of VA."
Where Charming Local History Meets Modern Comfort ~ Historic Fauquier County, VA
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Great place to stay . Clean , spacious and allow pets to stay . "
Melissa 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Winchester