Upperville Vacation Rentals

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Browse Select Upperville Vacation Homes

Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia
Outdoor pool
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia
10.0 out of 10, Exceptional, (48)
"Little Oatlands was the perfect place for our outdoor wedding and we’re very happy we chose it. If you are planning to do the same, and have family stay in the guest house for the weekend, read the contract *carefully*. We skimmed it and failed to realize that you’ll need to take all trash bags to the dumpster by the barn and strip all of the bed sheets and put them downstairs, etc…"
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia
Trailside Retreat in breathtaking Western Loudoun
Property grounds
Trailside Retreat in breathtaking Western Loudoun
10.0 out of 10, Exceptional, (22)
"We had such a lovely time in Virginia. This property was so clean and well appointed. We also enjoyed the location right next to the W&OD trail."
Trailside Retreat in breathtaking Western Loudoun
Historic gem in the heart of downtown Hamilton! Trees and a private stream
Private kitchen
Historic gem in the heart of downtown Hamilton! Trees and a private stream
Historic gem in the heart of downtown Hamilton! Trees and a private stream
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Breathtaking views with an indoor private pool, come escape with us
Exterior
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (229)
"Loved the view, the pool, brewery and the 3 floors of spaces to sleep worked perfect for our group."
Breathtaking views with an indoor private pool, come escape with us
Big Sunny Family House
Fridge, microwave, oven, stovetop
Big Sunny Family House
10.0 out of 10, Exceptional, (12)
"Proximity to RMA campus worked perfectly for our extended family attending graduation ceremonies and celebrations."
Big Sunny Family House
Chic Front Royal Retreat Near Shenandoah River!
Fridge, microwave, stovetop, dishwasher
Chic Front Royal Retreat Near Shenandoah River!
10.0 out of 10, Exceptional, (5)
"The location was minutes from Skyline Drive and we were close to tons of hiking. Front and back yard were both fenced and great for my niece and my dogs. House was super clean and had everything we needed. Only suggestion is a bigger couch or more seating in the living room. It was a little tight trying to relax at night in front of the TV."
Chic Front Royal Retreat Near Shenandoah River!
Cozy home near Casino, Breweries, Historical attractions, National Park & more
Fridge, microwave, oven, stovetop
Cozy home near Casino, Breweries, Historical attractions, National Park & more
10.0 out of 10, Exceptional, (13)
"We were in town for the comedy show at the casino. House was within walking distance however not a walk you would want to take wearing heels. Very quiet neighborhood with plenty of restaurants close by. The house was very clean and comfortable beds. Had a really great time!! Thank you!!!"
The price is CA $185
CA $395 total
includes taxes & fees
Jul 2 - Jul 3
Cozy home near Casino, Breweries, Historical attractions, National Park & more
Hot Tub, Poker Table, River Access & Kayaks and Wineries
Smart TV, fireplace, table tennis, books
Hot Tub, Poker Table, River Access & Kayaks and Wineries
9.8 out of 10, Exceptional, (7)
"Everything was fine."
The price is CA $233
CA $593 total
includes taxes & fees
Jul 2 - Jul 3
Hot Tub, Poker Table, River Access & Kayaks and Wineries
Morrisonville Manor w/ Fire Pit & Hot Tub!
Fridge, microwave, stovetop, dishwasher
Morrisonville Manor w/ Fire Pit & Hot Tub!
10.0 out of 10, Exceptional, (27)
"There were 9 adults and 1 baby in our group and the property worked out great for us. The owners had great communication and everything about the home came as advertised. Plenty of room, very clean, and some nice extra touches. We recommend and would stay here again."
Morrisonville Manor w/ Fire Pit & Hot Tub!
Bull Run Estate: Luxury Retreat w/ Scenic Views by RedAwning
Smart TV, fireplace
Bull Run Estate: Luxury Retreat w/ Scenic Views by RedAwning
10.0 out of 10, Exceptional, (1)
"Great for lots of family and friends so everyone is together and not hotel room or hotel lobby hopping"
Bull Run Estate: Luxury Retreat w/ Scenic Views by RedAwning
Sunny Front Royal Vacation Rental w/ Hot Tub!
Property grounds
Sunny Front Royal Vacation Rental w/ Hot Tub!
9.8 out of 10, Exceptional, (6)
"The house was newly renovated, clean, well stocked and spacious. My husband and I spent a long weekend hiking and enjoying the change of the season."
Sunny Front Royal Vacation Rental w/ Hot Tub!
Modern Townhome within walking distance of Old Town Winchester and attractions
Fridge, microwave, oven, stovetop
Modern Townhome within walking distance of Old Town Winchester and attractions
10.0 out of 10, Exceptional, (4)
"John was super helpful and the place was lovely."
Modern Townhome within walking distance of Old Town Winchester and attractions
Harpers Ferry Cottage: Hot Tub, WiFi, Dog-Friendly
TV, fireplace, books, stereo
Harpers Ferry Cottage: Hot Tub, WiFi, Dog-Friendly
6.0 out of 10, (1)
"Location was good. But the house needs some updates and a good cleaning. The tub is clogged. The sofa had odor. Too much clutter for dog friendly house. However, we did appreciate our stay."
The price is CA $141
CA $394 total
includes taxes & fees
Jul 8 - Jul 9
Harpers Ferry Cottage: Hot Tub, WiFi, Dog-Friendly
Old Post Office in Historic Town
Property grounds
Old Post Office in Historic Town
Old Post Office in Historic Town
Terra Alta - Incredible River Views and Hot Tub!
Property grounds
Terra Alta - Incredible River Views and Hot Tub!
9.8 out of 10, Exceptional, (44)
"Stayed here for work. Had 5 guys at the house. Plenty of room and great deck to hang out on."
The price is CA $234
CA $652 total
includes taxes & fees
Jun 25 - Jun 26
Terra Alta - Incredible River Views and Hot Tub!
Gruner Bungalow at Otium Cellars
Smart TV, table tennis, books, offices
Gruner Bungalow at Otium Cellars
9.8 out of 10, Exceptional, (83)
"This was a beautiful home for a 30 something Bachelorette Weekend. The proximity to the tasting room was convenient and the grounds were beautiful. Our groups had an excellent time and hope to be back!"
Gruner Bungalow at Otium Cellars
Modern Country House on the Shenandoah River
Property grounds
Modern Country House on the Shenandoah River
9.8 out of 10, Exceptional, (22)
"Highly recommend we had a blast. House is very well outfitted and for our 3 couples we each had our own bathroom which is a glorious thing. Beautiful views, three firepits and the lake made the outdoor space just what we needed. The climb back up to the house from the lake is no joke not for the elderly but our group of fifty something’s did ok and it was worth it. I’d recommend and may even see about going back for Harper’s Ferry. Well done Songyee and Jeff we appreciate you."
Modern Country House on the Shenandoah River
Historic and Updated Farmhouse Built in 1808
Property grounds
Historic and Updated Farmhouse Built in 1808
10.0 out of 10, Exceptional, (114)
"We had a great stay! Thank you!"
Historic and Updated Farmhouse Built in 1808
Luxury KING Suites, Lakefront w/ Dock, HotTub, Watercraft
TV, fireplace, stereo
Luxury KING Suites, Lakefront w/ Dock, HotTub, Watercraft
10.0 out of 10, Exceptional, (1)
"We stayed at Loving Gallery & Studio last weekend with a group of 15 for our Mothers 90th Birthday The home is just beautiful and well laid out for large groups. There are 6 beautiful bedrooms plus sofa beds and all the possible amenities! Lots of wood for stoves, fireplaces & firepit, bathroom amenities, bottled water in each room, well stocked kitchen with spices and everything you could possibly need for cooking in your home away from home. There are also several beautiful outdoor spaces to...
The price is CA $2,532
CA $3,391 total
includes taxes & fees
Jul 11 - Jul 12
Luxury KING Suites, Lakefront w/ Dock, HotTub, Watercraft
Family Gathering Space with a PRIVATE TRAIL WALK TO WINE!
Property grounds
Family Gathering Space with a PRIVATE TRAIL WALK TO WINE!
10.0 out of 10, Exceptional, (40)
"We had a wonderful time and everything was just as described"
Family Gathering Space with a PRIVATE TRAIL WALK TO WINE!
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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.

Other property types in Upperville

Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Smart TV, DVD player, books, video library
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
10.0 out of 10, Exceptional, (31)
"Very clean. Crisp, clean linens. Gorgeous views and surroundings. Extremely responsive. Highly recommend!!"
The price is CA $198
CA $452 total
includes taxes & fees
Jul 10 - Jul 11
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Breathtaking views with an indoor private pool, come escape with us
Exterior
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (229)
"Loved the view, the pool, brewery and the 3 floors of spaces to sleep worked perfect for our group."
Breathtaking views with an indoor private pool, come escape with us
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
Property grounds
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
9.6 out of 10, Exceptional, (10)
"We enjoyed the cabin very much. We hiked during the day and was very relaxing coming back to the hot tub and a fire. Thank you for a great stay!!"
The price is CA $215
CA $559 total
includes taxes & fees
Jun 23 - Jun 24
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
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.

Upperville Vacation Homes information

Number of reviews
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 Vacation Homes
Lowest Price
Highest Price

Recent Reviews in Upperville
Expedia verified reviews

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

5/5 Excellent
"Awesomeness at it's best!!!"
A verified traveller stayed at Microtel Inn & Suites by Wyndham Winchester
Posted 21 hours ago
Microtel Inn & Suites by Wyndham Winchester