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Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Upperville Vacation Homes

Cottage on King | Charming Historic Leesburg Home
Relax in this inviting outdoor seating area with sofas, armchairs, and a central table featuring a fire feature.

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 CA $182
CA $420 total
includes taxes & fees
Aug 11 - Aug 12
Cottage on King | Charming Historic Leesburg Home
Modern Country House on the Shenandoah River
Escape to a serene lakeside haven surrounded by nature, featuring a charming gazebo and tree stumps.

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (36)
"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
Modern kitchen with stove, refrigerator, and sink, featuring a central island with ample workspace.

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

9.8 out of 10, Exceptional, (98)
"Our stay was great and really enjoyed the house. We had so much space to have our own time and then still be able to come together for meals and hanging in the hot tub. We now want to come back in the winter and go to the sledding hill right in front of the house! "
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, (2)
"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 CA $137
CA $454 total
includes taxes & fees
Aug 25 - Aug 26
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
A unique mountaintop getaway overlooking Willow Croft Winery.
Relax by the fire pit in the lodge's outdoor patio area, surrounded by comfortable seating and dining tables.

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 CA $433
CA $831 total
includes taxes & fees
Aug 12 - Aug 13
A unique mountaintop getaway overlooking Willow Croft Winery.
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Relax in a cozy forest setting with two Adirondack chairs surrounding a warm fire pit.

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

8.4 out of 10, Very good, (5)
"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 CA $297
CA $683 total
includes taxes & fees
Aug 12 - Aug 13
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 CA $206
CA $328 total
includes taxes & fees
Aug 25 - Aug 26
Mountain View Bungalow in Front Royal
Breathtaking View with an Indoor Pool
Relax on the wrap-around veranda or patio, surrounded by lush greenery.

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (256)
"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 CA $234
CA $611 total
includes taxes & fees
Aug 14 - Aug 15
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Relax in style with a hot tub and lounge chairs on the deck, surrounded by lush greenery and twinkling lights.

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 CA $212
CA $513 total
includes taxes & fees
Aug 11 - Aug 12
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Rural Home, Hot Tub, Campfire, Hardwood Floors
Enjoy a classic suburban feel in this two-story brick home with a spacious backyard and open garage.

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!
Relax in this spacious living room with a high ceiling and large windows, featuring a comfortable sofa set and a television on a stand.

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!
Kitchen features a window, dishwasher, oven, microwave, and a decorative vase with flowers.

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!
Relax in a serene hot tub on a raised deck with breathtaking views of the surrounding forest.

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 CA $138
CA $560 total
includes taxes & fees
Aug 21 - Aug 22
Terra Alta - Incredible River Views and Hot Tub!
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Enjoy cooking in this well-equipped kitchen with a refrigerator, stainless steel range, and microwave.

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
Enjoy a warm evening by the fire in this outdoor space.

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

9.8 out of 10, Exceptional, (57)
"WE HAD A NICE WEEKEND AT THE HOUSE .THE KITCHEN UTENSILS HAS SEEN BETTER DAYS. FYI THE HOUSE IS RIGHT N3XT TL A BUSY ROAD.WE ENJOYED THE HOTTUB AND TV COUCH AREA. THE QINERY NEXT DOOR WAS REALLY NICE"
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Relax in an outdoor space surrounded by lush greenery and a wooden fence.

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!"
The price is CA $175
CA $570 total
includes taxes & fees
Aug 13 - Aug 14
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Where Charming Local History Meets Modern Comfort ~ Historic Fauquier County, VA
Guest house surrounded by lush greenery and flowering trees, offering a patio with outdoor seating and barbecue grill.

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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"I’ve stayed here before with my two dogs, this time without…..Rooms are very spacious and clean, Staff at desk always friendly and helpful. Breakfast good with friendly staff….Convenient off/on from Highway."
Laura 1-night trip
Posted 1 day ago
Comfort Inn & Suites Winchester