Upperville Holiday Homes from £170: Search Holiday Homes in Upperville

A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Upperville holiday homes

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

1. 1910 Farmhouse on 6 Acres • VA Wine Country

Marshall

Erick U.

includes taxes & fees

17 Nov - 18 Nov

A spacious living room with a wooden coffee table, two leather sofas, a hanging light fixture, and a view of the adjacent kitchen.

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

Front Royal

includes taxes & fees

26 Oct - 27 Oct

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

3. Mountain home w/ hot tub & sunroom

Front Royal

Mollie S.

includes taxes & fees

3 Nov - 4 Nov

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

4. super cosy cottage with high speed internet!

Middleburg

Lynette

includes taxes & fees

29 Oct - 30 Oct

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

5. Spacious Modern Home on Middleburg Horse Farm

Middleburg

Denise B.

includes taxes & fees

26 Oct - 27 Oct

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

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

Shenandoah Farms

"We were looking for a comfortable home base to explore Front Royal and Skyline Plaza, and this was perfect! A modernized home with enough amenities that we were tempted every day to just stay “home!” The kids loved the reading nook and cozy sitting areas, and the fire pit and clean, working hot tub were big pluses as well. Kitchen was roomy, with great appliances and plenty of counter space. Beds were comfortable. Bathrooms were nice and modern. Lots of closet space, too. When we left, the kids...

Joshua J.

includes taxes & fees

28 Oct - 29 Oct

A fire feature with a glass enclosure, a wicker sofa with cushions, and a wooden deck with string lights.

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

Apple Mountain Lake

includes taxes & fees

26 Oct - 27 Oct

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

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

Front Royal

includes taxes & fees

28 Oct - 29 Oct

A deck with outdoor seating and a lake view.

9. Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Harpers Ferry

Dawn S.

includes taxes & fees

26 Oct - 27 Oct

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

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

Hume

includes taxes & fees

26 Oct - 27 Oct

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

11. Pool Table, Fireplace & Deck near Shenandoah Park

Front Royal

"Home was clean and looked like it had recently been remodeled/updated. The host was very responsive and when the oven wasn't working properly, they went to Lowes and purchased a new one immediately! Made our short trip much easier not having to eat out or find a last minute option for our kids/babysitter on Friday evening. We were only in town from Thursday-Sunday, and it was perfect for the 5 of us. The pool table was a fun addition for the kids. The only minor complaint I have is that I wish I...

Crystal H.

includes taxes & fees

28 Oct - 29 Oct

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

12. Mountain View Bungalow in Front Royal

Front Royal

HEMANT S.

includes taxes & fees

29 Oct - 30 Oct

A dining area with a wooden ceiling, a kitchen with blue cabinets, and a tiled floor.

13. Main Street USA -- Walk to Everything

Purcellville

melissa b.

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.

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

Harpers Ferry

Erin C.

includes taxes & fees

2 Nov - 3 Nov

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

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

Shannondale

Anonymous traveller

includes taxes & fees

25 Oct - 26 Oct

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

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

Harpers Ferry

Brian S.

includes taxes & fees

27 Oct - 28 Oct

17. Still Meadow Farm

Purcellville

Jodie J.

includes taxes & fees

2 Nov - 3 Nov

A living room with a blue sofa, wooden beams, a TV, and a kitchen in the background.

18. Greek Spa - Frisbee Golf - Stone fire Pizza Oven

Front Royal

includes taxes & fees

16 Nov - 17 Nov

A large, multi-story lodge with a prominent balcony, situated by a lake with a stone pathway leading to the entrance.

19. LUX Lakefront King Suites w/Dock, HotTub, Kayaks

Shannondale

Tom V.

includes taxes & fees

17 Nov - 18 Nov

A modern living room with a stone fireplace, white walls, and a high ceiling.

20. Chalet in Harpers Ferry

Harpers Ferry

Courtney C.

includes taxes & fees

27 Oct - 28 Oct

View all properties

Find holiday rentals that suit your style

Cabins

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Upperville Hotel Reviews

Comfort Inn & Suites Winchester

8/10 Good

"It was a nice hotel."

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"rooms are clean, spacious, and serviced everyday. Good breakfast on offer and the Bar is good too. Greal location and good parking. Staff very helpful and knowledgeable about the area. Shenandoah mountains are wonderful. Lots of wineries and farmers market near by"

Spark by Hilton Winchester

10/10 Excellent

"What a pleasure staying a night in such a new, sparkling clean hotel! Location was fantastic with lots of stores and restaurants and the Highway very close! Our room was extremely clean and comfy! The front desk clerk on the night of Oct 18 was fantastic and friendly! Breakfast was just Continental, but better than nothing!"

Salamander Resort And Spa

10/10 Excellent

"The Salamander resort is breathtaking! Spectacular property. The staff was always willing to answer questions or to help in any way possible. Our room was clean and very comfortable. I was so happy to see that it is pet friendly. My only complaint was that guests left their dogs in their rooms while they were out. I heard a few dogs that were clearly distressed at being left alone. As a dog owner, it really upset me. The guests should be required to not leave their pets alone."

Find out more about Upperville

Upperville Holiday Homes information

Number of reviews	189
Accommodation	253 Holiday Homes
Lowest Price	£170
Highest Price	£1,149

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Upperville on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Upperville holiday homes

1. 1910 Farmhouse on 6 Acres • VA Wine Country

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

3. Mountain home w/ hot tub & sunroom

4. super cosy cottage with high speed internet!

5. Spacious Modern Home on Middleburg Horse Farm

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

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

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

9. Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

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

11. Pool Table, Fireplace & Deck near Shenandoah Park

12. Mountain View Bungalow in Front Royal

13. Main Street USA -- Walk to Everything

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

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

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

17. Still Meadow Farm

18. Greek Spa - Frisbee Golf - Stone fire Pizza Oven

19. LUX Lakefront King Suites w/Dock, HotTub, Kayaks

20. Chalet in Harpers Ferry

Find holiday rentals that suit your style

Top Upperville Hotel Reviews

Comfort Inn & Suites Winchester

Country Inn & Suites by Radisson, Winchester, VA

Clarion Inn Harpers Ferry - Charles Town

The George Washington Hotel, A Wyndham Grand Hotel

Microtel Inn & Suites by Wyndham Winchester

Red Roof Inn Leesburg, VA

Travelodge by Wyndham Winchester

Spark by Hilton Winchester

Salamander Resort And Spa

Find out more about Upperville

Upperville Holiday Homes information

Explore a world of travel with Expedia