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Compare 249 Vacation Homes in Upperville with updated reviews, rates, and availability.

Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

9.8 out of 10, Exceptional, (29)
"Easy to book and communicate with PM. Greatly appreciate being pet friendly as we travel with our aging mini doxie. You are in the woods, so there are bugs folks. Plenty of bedrooms to choose from on two levels for those who want to channel their inner Goldilocks. Kitchen is stocked so that it is easy to cook meals and for the coffee/tea drinkers you don’t have to leave the floor you are on for another cup if you don’t want to. Plenty of parking as well if you are traveling as a group. Trail and...
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

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

9.6 out of 10, Exceptional, (91)
"Great family stay! Highly recommend "
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (31)
"This was a perfect long weekend stay for two families (4 adults, 4 kids). Comfortable, spacious, and well-equipped house on a beautiful property. Very responsive and helpful host. Would give 6 stars if I could. We hope to be back soon!"
Modern Country House on the Shenandoah River

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

9.8 out of 10, Exceptional, (47)
"With grandparents and 2 families with children, not only was the house perfect but the fenced yard was huge and spectacular. We didn’t use the hot tub, but there was plenty of good space for adults, too. We gathered for a family wedding, but the space enabled us to spend a few wonderful relaxing days with family we rarely see. Communication with Leora was prompt and accommodating. 5 stars all around! Thank you!"
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

Cottage on King | Charming Historic Leesburg Home

9.4 out of 10, Exceptional, (49)
"Location is great for walking to old town Leesburg. Very busy streets though, keep that in mind. Neighbors and owner were nice and not a problem. Parking can be tight for a larger vehicle. But a Yukon fits. Weather was freezing while we were there (nothing anyone can do about that) so we were stuck inside for our stay). Would be a good stop to base out of to explore historic downtown Leesburg. "
The price is AED 860
AED 1,474 total
includes taxes & fees
13 Apr - 14 Apr
Cottage on King | Charming Historic Leesburg Home

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

9.8 out of 10, Exceptional, (93)
"What a perfect home for our Thanksgiving celebration! There were so many rooms in which to spread out, the beds were comfortable, and the location was central to necessities. We had a great stay!"
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

The Lodge at Bear Rock

The Lodge at Bear Rock

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (43)
"This is our third year staying in this house and we love it. The company accommodates our requests and is quick to respond if we need anything. The house itself is laid out perfectly for what we need with lots of rooms for both kids and adults. "
Charles Town Home w/ Private Pool & Hot Tub

Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery

9.8 out of 10, Exceptional, (47)
"We had a wonderful stay at this house! The rooms were cozy and comfortable, perfect for relaxing after a day of activities. While the kitchen is a bit outdated, it still had everything we needed for preparing meals. The location was fantastic - close to everything we wanted to explore. My friends and family had a great time and we're definitely planning to return in the future. Highly Highly recommend "
Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery

Balcony & Pool Access: Modern Gainesville Home

Balcony & Pool Access: Modern Gainesville Home

Big Sunny Family House

10.0 out of 10, Exceptional, (28)
"The house was a beautiful, old farmhouse house. There were notes all around, giving clear guidance on where things were located. It was very clean and beautifully decorated. My favorite part was the large dining room table that allowed everyone to sit down and eat together. I would definitely stay there again."
Big Sunny Family House

Chic Front Royal Retreat Near Shenandoah River!

9.6 out of 10, Exceptional, (15)
"We had a wonderful stay at this property! The house was very clean, and the listing was completely accurate, which we really appreciated. Street parking was easy, making arrival and departure hassle-free. The home is perfect for a couple or even two couples, with a comfortable layout and plenty of space.One of the highlights was the great front and backyard, which our dog absolutely loved! It was a perfect setup for a pet-friendly getaway.The only minor issue was that the stairs felt slightly...
Chic Front Royal Retreat Near Shenandoah River!

Indulge in Elegance: 7 BR Manor with Events in Historic Waterford

Indulge in Elegance: 7 BR Manor with Events in Historic Waterford

Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

10.0 out of 10, Exceptional, (54)
"The property is quite lovely, surrounded by the rolling hills of western Virginia. The house was perfect, a lot of space to spread out if needed. We spent our evenings on the screened in back porch. The pool and gardens were an added bonus. Every evening the neighbor cows would graze along the fence line- just a lovely get away from the City! "
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

Modern Mountain Retreat w/ Deck + Hot Tub!

10.0 out of 10, Exceptional, (66)
"The owner communicated well and was very responsive. The fireplace stove was great and we used the hot tub every day. Kitchen was well stocked. We cooked almost every meal and had everything we needed. The office space is a nice, private, comfortable space, as well. "
Modern Mountain Retreat w/ Deck + Hot Tub!

Harpers Ferry Cottage: Hot Tub, WiFi, Dog-Friendly

9.0 out of 10, Wonderful, (6)
"We arrived in 13 degree weather from "
The price is AED 541
AED 1,052 total
includes taxes & fees
9 Apr - 10 Apr
Harpers Ferry Cottage: Hot Tub, WiFi, Dog-Friendly

Mountain Getaway - 7 beds (2 King) - Large Common Area

10.0 out of 10, Exceptional, (10)
"This place was everything and more. We had quite a large group coming in for a weekend trip, and this place was able to fit all of us. The pictures do not do it justice because this place was beautiful, clean, and spacious. Would love to come back one day!"
Mountain Getaway - 7 beds (2 King) - Large Common Area

Cozy home near Casino, Breweries, Historical attractions, National Park & more

9.8 out of 10, Exceptional, (25)
"My wife and I had a wonderful stay at the Wilt House! Charles Town was a great visit and we plan to go back soon!"
The price is AED 514
AED 1,093 total
includes taxes & fees
7 Apr - 8 Apr
Cozy home near Casino, Breweries, Historical attractions, National Park & more

Shenandoah River-hiking, fishing, wineries, breweries & more

9.6 out of 10, Exceptional, (25)
"Had a great time loved the house and location "
Shenandoah River-hiking, fishing, wineries, breweries & more

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV

9.6 out of 10, Exceptional, (11)
"The house was very clean and well maintained. It is the perfect place to stay for a trip to Harpers Ferry and is a short drive to Charles Town, Shepherdstown and the Antietam Battlefield. "
The price is AED 731
AED 1,836 total
includes taxes & fees
15 Apr - 16 Apr
Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
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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Other property types in Upperville

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (83)
"Loved it "
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

Cozy Mountain Cabin w/ Steam Shower! Great for Couples.

10.0 out of 10, Exceptional, (60)
"The cabin was beautiful! Brigid has the cabin well stocked. She was very welcoming. Our family with kids and a dog felt very comfortable and even pampered!"
The price is AED 588
AED 1,280 total
includes taxes & fees
6 May - 7 May
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (38)
"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities. "
The price is AED 1,010
AED 1,446 total
includes taxes & fees
10 Apr - 11 Apr
18th Century Stone Cottage minutes from historic Middleburg
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.