Upperville, VA Vacation Homes from AED 781

Upperville Vacation Homes
Virginia
United States of America
Expedia.ae

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Our top choices for Upperville vacation homes

A two-story house with a porch, surrounded by trees and grass.

A dining area with a wooden table, white chairs, a chandelier, and large windows with views of greenery.

A living room with a sofa, TV, fireplace, and large windows.

An American flag hanging from a porch, surrounded by greenery and trees.

1. 1910 Farmhouse on 6 Acres • VA Wine Country

1910 Farmhouse on 6 Acres • VA Wine Country

Marshall

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"If we managed to do everything, sing, dance, play, we loved the comfortable place for us"

Erick U.

The price is AED 588

AED 588

AED 1,304 total

includes taxes & fees

1 Dec - 2 Dec

1910 Farmhouse on 6 Acres • VA Wine Country

A modern kitchen with a central island, wooden chairs, stainless steel appliances, and pendant lighting.

A circular fire pit with six Adirondack chairs arranged around it on a grassy lawn.

A compact kitchen with white cabinets, a black refrigerator, and a dining area with a round table and chairs.

A kitchen with white cabinets, a microwave, a coffee maker, a sink, and a window.

2. Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6

Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6

Front Royal

The price is AED 544

AED 544

AED 1,495 total

includes taxes & fees

4 Nov - 5 Nov

Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6

A spacious kitchen with modern appliances, a dining area with a large table and chairs, and a view through a glass door.

A living room with a fireplace, a beige armchair, and a black ottoman.

A modern living room with a dining area, large windows, and a sofa with a red cushion.

A covered porch with stone flooring, two chairs, a rug, and a glass door with a black frame.

3. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm

Middleburg

10.0 out of 10, Exceptional, (22 reviews)

10/10

Exceptional

(22 reviews)

"Perfect for a mother and daughter get away. Peaceful and quiet. Short distance to Middleburg. Looking forward to staying here again. Already planning another trip with the whole family at Thanksgiving!"

Denise B.

The price is AED 1,190

AED 1,190

AED 2,148 total

includes taxes & fees

1 Dec - 2 Dec

Spacious Modern Home on Middleburg Horse Farm

A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

Loft area perfect for family game night or hangout space.

A covered porch with white chairs and a table, large windows offering a view of greenery.

Open floor plan perfect for spending time with family and friends.

4. Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom

Front Royal

9.0 out of 10, Wonderful, (32 reviews)

9.0/10

Wonderful

(32 reviews)

"The cottage was amazing!! The hot tub was great and check in was super easy :) Internet and phone service were very good, and the cottage was stocked with all the kitchen utensils and linens we could have needed!"

Mollie S.

The price is AED 629

AED 629

AED 1,170 total

includes taxes & fees

3 Nov - 4 Nov

Mountain home w/ hot tub & sunroom

A kitchen with a large island, wooden cabinets, a microwave, a coffee maker, and a window above the sink.

A rural property with a dirt road, wooden fences, and leafless trees.

A modern kitchen with a round wooden table, wooden chairs, a built-in cabinet with glass doors, a window, and a woven wall hanging.

A two-story house with a balcony, a garage, and a fenced yard.

5. super cosy cottage with high speed internet!

super cosy cottage with high speed internet!

Middleburg

9.6 out of 10, Exceptional, (19 reviews)

9.6/10

Exceptional

(19 reviews)

"The area was surrounded by horses, Horse farms all around, which was lovely. Very quite and peaceful. Enjoyed my time there."

Lynette

The price is AED 606

AED 606

AED 1,089 total

includes taxes & fees

1 Dec - 2 Dec

super cosy cottage with high speed internet!

Local wineries, breweries, and small-town charm in Front Royal

A modern kitchen with green cabinets, a central island, and a dining area with a table and chairs.

A deck with a hot tub, wooden chairs, and a table.

6. Mountain Views w/Hot Tub, 95” TV & Trail Access

Mountain Views w/Hot Tub, 95” TV & Trail Access

Shenandoah Farms

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"Just as described."

Matt F.

The price is AED 926

AED 926

AED 1,737 total

includes taxes & fees

3 Nov - 4 Nov

Mountain Views w/Hot Tub, 95” TV & Trail Access

7. Hunters Retreat with High Speed Internet

Hunters Retreat with High Speed Internet

Middleburg

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"We had the best fall weekend and the property is amazing "

Kelly T.

Hunters Retreat with High Speed Internet

A deck with a table set for two, featuring a bottle of champagne, glasses, and a candle.

A modern living room with a sectional sofa, a coffee table, and a TV displaying a Netflix interface.

A living room with a TV displaying Netflix content, a remote control, a candle, and a stack of books on a coffee table.

A dining table with white chairs, a vase with green foliage, and a lit candle.

8. Cozy 3BR Retreat | Perfect for Families & Groups

Cozy 3BR Retreat | Perfect for Families & Groups

Apple Mountain Lake

The price is AED 726

AED 726

AED 1,287 total

includes taxes & fees

3 Nov - 4 Nov

Cozy 3BR Retreat | Perfect for Families & Groups

A hot tub in a forested area with a rocky ground and trees.

A modern kitchen with white cabinets, a stainless steel refrigerator, and an oven.

A modern kitchen with white cabinets, stainless steel appliances, and a window with a view.

A bedroom with a bed, a ceiling fan, two windows, a nightstand, a lamp, and a painting.

9. The Blue Jay | New House in the Woods w/ Hot Tub

The Blue Jay | New House in the Woods w/ Hot Tub

Harpers Ferry

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Great place. Very well stocked house everything you need Great response from host. Very nice place. Road is a little rough as explained in listing "

Brett D.

The price is AED 367

AED 367

AED 1,472 total

includes taxes & fees

1 Nov - 2 Nov

The Blue Jay | New House in the Woods w/ Hot Tub

A deck with outdoor seating and a lake view.

A garden with a stone pathway, surrounded by various plants and trees.

A beach with two empty lounge chairs facing a calm lake, surrounded by a chain-link fence and a dock in the background.

A spacious hallway with a wooden floor, a stone wall, and a dining area with a table and chairs.

10. Mountain Lake Retreat Harpers Ferry:Hot Tub, Firepit, Fenced Yard, Beach, Winery

Mountain Lake Retreat Harpers Ferry:Hot Tub, Firepit, Fenced Yard, Beach, Winery

Harpers Ferry

9.8 out of 10, Exceptional, (16 reviews)

9.8/10

Exceptional

(16 reviews)

"We had a lovely stay and it was so nice for our dog as well. The Mountain Lake Cub had a doggy beach day on Saturday morning and it was a super fun experience. The host was friendly and responsive!"

Dawn S.

The price is AED 238

AED 238

AED 1,099 total

includes taxes & fees

5 Nov - 6 Nov

Mountain Lake Retreat Harpers Ferry:Hot Tub, Firepit, Fenced Yard, Beach, Winery

A lakeside property with a dock, a wooden deck, and a house surrounded by dense greenery.

A spacious living room with a large window, a fireplace, and a bookshelf.

A lakeside view with a wooden dock, two chairs, and a house in the background.

A modern kitchen with white cabinetry, a central island with stools, a ceiling fan, and a view to the outdoors.

11. Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6

Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6

Front Royal

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"The gravel road to get to the properly is an adventure. The owner described it perfectly."

Denise A.

The price is AED 508

AED 508

AED 1,513 total

includes taxes & fees

2 Nov - 3 Nov

Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6

A rustic interior with a wooden dining table, chairs, and a fireplace.

A rustic log cabin interior with a wooden door, a lamp, a small round table, and two people seated on a sofa.

A man pouring a drink into a woman's glass in a rustic room with stone walls and wooden beams.

A rustic interior with exposed wooden beams, a stone fireplace, and a wooden dining area.

12. Historic 6BR • EventsandConcierge! • Pool • Wineries

Historic 6BR • EventsandConcierge! • Pool • Wineries

Hume

The price is AED 1,358

AED 1,358

AED 4,548 total

includes taxes & fees

1 Nov - 2 Nov

Historic 6BR • EventsandConcierge! • Pool • Wineries

A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

A bed with white bedding, a wooden headboard, and two wall-mounted lamps.

A modern kitchen with wooden cabinets, a stone fireplace, and a bar area with stools.

A living room with a flat-screen TV mounted on a white wall, wooden flooring, and a staircase with wooden railings.

13. Pool Table, Fireplace & Deck near Shenandoah Park

Pool Table, Fireplace & Deck near Shenandoah Park

Front Royal

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Great location. Very quiet neighborhood good for walking"

tom c.

The price is AED 659

AED 659

AED 1,649 total

includes taxes & fees

2 Nov - 3 Nov

Pool Table, Fireplace & Deck near Shenandoah Park

A wooden deck with white railings and a covered porch area.

A single-story house with a covered porch, white railings, and a chimney.

A bedroom with a bed, a dresser, a window, and a mirror.

14. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal

Front Royal

10.0 out of 10, Exceptional, (47 reviews)

10/10

Exceptional

(47 reviews)

"Perfect place- would stay here again."

HEMANT S.

The price is AED 496

AED 496

AED 781 total

includes taxes & fees

1 Nov - 2 Nov

Mountain View Bungalow in Front Royal

A hot tub under a wooden pergola with a view of autumn trees.

A dining area with a long table set for a meal, a hanging light fixture, and a sofa in the background.

A living room with a fireplace, a sofa, a chair, a coffee table, and a TV mounted on the wall.

A two-story cabin with a balcony, surrounded by trees with autumn foliage.

15. Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Harpers Ferry

9.8 out of 10, Exceptional, (16 reviews)

9.8/10

Exceptional

(16 reviews)

"We had a great stay "

Lauren O.

The price is AED 367

AED 367

AED 1,472 total

includes taxes & fees

18 Nov - 19 Nov

Huckleberry Hills | Hot Tub & Fire Pit & Dogs

A spacious living room with a green sofa set, a coffee table, and a fireplace. There is a kitchen in the background with a large window overlooking a deck.

A modern kitchen with white cabinets, stainless steel appliances, and a view of the outdoors.

A modern living room with two leather chairs, a small table, a rug, and a large window with a view of trees.

A large, modern house with a balcony, surrounded by a forest and rocky terrain.

16. Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Harpers Ferry

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

"Welcoming host, great place!"

Amanda M.

The price is AED 313

AED 313

AED 1,087 total

includes taxes & fees

3 Nov - 4 Nov

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

17. Still Meadow Farm

Still Meadow Farm

Purcellville

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Still Meadow is a beautiful place to stay, super clean, We would definitely recommend. Host was responsive and accommodating."

Jodie J.

The price is AED 2,700

AED 2,700

AED 4,646 total

includes taxes & fees

9 Nov - 10 Nov

Still Meadow Farm

A cozy dining area with a table and chairs, a view of a balcony with a railing, and a warm interior with wooden walls.

A wooden cabin interior with a checkered floor, a chandelier, and a framed picture on the wall.

A kitchen with wooden walls, a window with a view of trees, a sink, and a stove.

A log cabin interior with a fireplace, a green sofa, and a large window overlooking a body of water.

18. Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge

Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge

Shannondale

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"My family and ai had an amazing stay at Deb and Alex’s rental in WV! It was easy to check-in, very clean, and had convenient amenities! Would definitely consider staying with them again!"

Anonymous traveler

The price is AED 913

AED 913

AED 1,770 total

includes taxes & fees

1 Dec - 2 Dec

Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge

A spacious dining area with a wooden table and chairs, large windows with a view of trees, and a stone wall in the background.

An aerial view of a house with a large deck, surrounded by trees and a dry landscape.

A dining area with a wooden table, green chairs, and a white cabinet with glass doors.

A stone-walled room with a fireplace, a sofa, and a wooden floor.

19. Stone Cabin on Valley View: Fire Pit + Hot Tub

Stone Cabin on Valley View: Fire Pit + Hot Tub

Harpers Ferry

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"Beautiful scenery! Beautiful home! Wonderful hosts!"

Brian S.

The price is AED 667

AED 667

AED 1,412 total

includes taxes & fees

3 Nov - 4 Nov

Stone Cabin on Valley View: Fire Pit + Hot Tub

A modern living room with a sofa, yellow chairs, a dining table, and a TV mounted on the wall.

A bedroom with a wooden bed, white bedding, a ceiling fan, bedside lamps, a small stool, and a window with blinds.

A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a patterned rug.

A small, single-story house with a front porch, a small garden, and a tree.

20. Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard

Leesburg

10.0 out of 10, Exceptional, (39 reviews)

10/10

Exceptional

(39 reviews)

"Clean sweet place to stay and relax. Couldn't have been nicer."

Avis V.

The price is AED 532

AED 532

AED 1,174 total

includes taxes & fees

11 Nov - 12 Nov

Leesburg Hideaway- King Bed + Private Backyard

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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