Holiday Homes in Upperville

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Check prices for these dates

Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct

Featured Holiday Homes in Upperville

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, (8)
"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."
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 AU$373
includes taxes & fees
5 Sept - 6 Sept
Mountain View Bungalow in Front Royal
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 AU$427
includes taxes & fees
1 Sept - 2 Sept
Cottage on King | Charming Historic Leesburg Home
Terra Alta - Incredible River Views and Hot Tub!
Exterior

Terra Alta - Incredible River Views and Hot Tub!

9.6 out of 10, Exceptional, (58)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
The price is AU$631
includes taxes & fees
1 Sept - 2 Sept
Terra Alta - Incredible River Views and Hot Tub!
Modern Country House on the Shenandoah River
Property grounds

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (39)
"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
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Fridge, microwave, oven, stovetop

YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

10.0 out of 10, Exceptional, (103)
"We stay at Yellowwood every year. It is on a quiet lane in the most picturesque part of Virginia (if not the country)!Also, Middleburg is just a short drive (or walk) away.We love Yellowwood!"
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
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 perfect 3 bed/3.5 bath new build cabin for a get away with friends or family. We have nothing negative to say about this property. Our stay was Amazing."
The price is AU$931
includes taxes & fees
2 Sept - 3 Sept
A unique mountaintop getaway overlooking Willow Croft Winery.
Breathtaking View with an Indoor Pool
Outdoor dining

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (258)
"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
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!
Where Charming Local History Meets Modern Comfort ~ Historic Fauquier County, VA
Outdoor dining

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

9.8 out of 10, Exceptional, (69)
"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
Spacious home steps from Main St and Shenandoah NP with firepit & large backyard
Fridge, microwave, oven, stovetop

Spacious home steps from Main St and Shenandoah NP with firepit & large backyard

10.0 out of 10, Exceptional, (14)
"We needed a place to stay for our golf foursome. Thisfour bedroom property met all of our needs."
The price is AU$598
includes taxes & fees
26 Aug - 27 Aug
Spacious home steps from Main St and Shenandoah NP with firepit & large backyard
Welcome to the Ladybug Retreat!
Microwave, oven, stovetop, dishwasher

Welcome to the Ladybug Retreat!

10.0 out of 10, Exceptional, (1)
"This home is lovely and the host has thought of everything. We will definitely stay here again. "
The price is AU$630
includes taxes & fees
8 Sept - 9 Sept
Welcome to the Ladybug Retreat!
Mulberry Manor House<br> Spacious, Private & Peaceful Retreat -
Exterior

Mulberry Manor House<br> Spacious, Private & Peaceful Retreat -

10.0 out of 10, Exceptional, (22)
"Clean, spacious, very well-equipped. We enjoyed our stay very much."
Mulberry Manor House<br> Spacious, Private & Peaceful Retreat -
Secluded 4 bedroom log style home with screened porches, deck and fishing pond.
Smart TV, printers

Secluded 4 bedroom log style home with screened porches, deck and fishing pond.

2.0 star property
10.0 out of 10, Exceptional, (2)
"Super relaxing stay…..many thanks!"
Secluded 4 bedroom log style home with screened porches, deck and fishing pond.
The Apple Mountain House
Interior

The Apple Mountain House

9.4 out of 10, Exceptional, (3)
"Amazing place to relax."
The price is AU$595
includes taxes & fees
27 Aug - 28 Aug
The Apple Mountain House
The Nest at Chester Gap
Terrace/patio

The Nest at Chester Gap

10.0 out of 10, Exceptional, (100)
"Very enjoyable; peaceful, isolated--excellent place to relax; good hiking nearby "
The Nest at Chester Gap
Grand 9BR Provenance Manor Ideal for Weddings & Gatherings
Private kitchen

Grand 9BR Provenance Manor Ideal for Weddings & Gatherings

The price is AU$2,829
includes taxes & fees
3 Sept - 4 Sept
Grand 9BR Provenance Manor Ideal for Weddings & Gatherings
Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA
Fridge, microwave, oven, stovetop

Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA

The price is AU$880
includes taxes & fees
8 Sept - 9 Sept
Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
Terrace/patio

Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!

9.8 out of 10, Exceptional, (23)
"Great stay for two young families. Lovely home and great location. Would recommend for a group trip to the area."
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
Hot tub, Campfire ring and great location!
Interior

Hot tub, Campfire ring and great location!

9.4 out of 10, Exceptional, (120)
"We had an amazing time in WV. The home was comfortable and met all of our needs. It was quiet and relaxing, but close to the major attractions for the action."
Hot tub, Campfire ring and great location!
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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"Country Inn and Suites is just what we needed after a long day of driving. Check in was easy, the front desk was kind and helpful while the room was cool and comfortable. I will say that the property needs some updating. Waffle machine is broken, walls need paint in the hallways and rooms. We slept well and left rested. Thank you "
Lisabeth 1-night trip
Posted 1 day ago
Country Inn & Suites by Radisson, Winchester, VA