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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

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

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

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

9.8 out of 10, Exceptional, (28)
"We had a great time visiting with family and getting our much needed rest and relaxation at your beautiful house. Thanks!"
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Property grounds

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
Property grounds

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
Terrace/patio

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
Terrace/patio

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 SAR 698
SAR 1,268 total
includes taxes & fees
31 Mar - 1 Apr
Cottage on King | Charming Historic Leesburg Home
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, (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
Smart TV, fireplace, video games, foosball

The Lodge at Bear Rock

The Lodge at Bear Rock
Charles Town Home w/ Private Pool & Hot Tub
Pool

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (41)
"Our families decided to rent the property for a getaway close to the DMV. It was easy to check in, get around Charles Town and enjoy the property. Even with an unexpected 6" of snow, we still found time to appreciate everything the property had to offer."
Charles Town Home w/ Private Pool & Hot Tub
Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery
Terrace/patio

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
Children's area

Balcony & Pool Access: Modern Gainesville Home

Balcony & Pool Access: Modern Gainesville Home
Big Sunny Family House
Fridge, microwave, oven, stovetop

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!
Fridge, microwave, stovetop, dishwasher

Chic Front Royal Retreat Near Shenandoah River!

9.4 out of 10, Exceptional, (13)
"Fit all our needs. Enjoyed the area. "
Chic Front Royal Retreat Near Shenandoah River!
Indulge in Elegance: 7 BR Manor with Events in Historic Waterford
6 bedrooms, desk, iron/ironing board, WiFi

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
Property grounds

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!
Fridge, microwave, stovetop, dishwasher

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
TV, fireplace, books, stereo

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 SAR 553
SAR 1,070 total
includes taxes & fees
1 Apr - 2 Apr
Harpers Ferry Cottage: Hot Tub, WiFi, Dog-Friendly
Mountain Getaway - 7 beds (2 King) - Large Common Area
Terrace/patio

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
Terrace/patio

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

9.8 out of 10, Exceptional, (24)
"We loved the home’s decor. Well supplied with basics, plus complimentary snacks and a bottle of wine! Would have appreciated the heat being turned on before our arrival on what was a freezing cold day. Hosts very responsive whenever we reached out. If you don’t love very firm, very thick bed pillows, suggest you bring your own. Overall, we enjoyed our stay at the Wilt House."
The price is SAR 525
SAR 1,117 total
includes taxes & fees
30 Mar - 31 Mar
Cozy home near Casino, Breweries, Historical attractions, National Park & more
Shenandoah River-hiking, fishing, wineries, breweries & more
Exterior

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

9.6 out of 10, Exceptional, (24)
"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
Outdoor spa tub

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. "
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

Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
Smart TV, DVD player, books, video library

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

10.0 out of 10, Exceptional, (59)
"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 SAR 581
SAR 1,274 total
includes taxes & fees
31 Mar - 1 Apr
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

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.
Hot Tub, Game Room, River Access, Fire Pit & Grill
Interior

Hot Tub, Game Room, River Access, Fire Pit & Grill

9.6 out of 10, Exceptional, (22)
"This was a perfect place for our group. Bedroom for everyone, up and down tvs for movie and sports watching, table for gaming, and hrs in the hot tub. Dining table was big enough for everyone to eat together, and the kitchen had what we needed to manage all our meals"
The price is SAR 837
SAR 1,472 total
includes taxes & fees
1 Apr - 2 Apr
Hot Tub, Game Room, River Access, Fire Pit & Grill
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.