Upperville Holiday Homes from €195: Search Top House Rentals

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

10 Nov - 11 Nov

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

2. super cosy cottage with high speed internet!

Middleburg

Lynette

includes taxes & fees

15 Nov - 16 Nov

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

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

Front Royal

includes taxes & fees

4 Nov - 5 Nov

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

4. Mountain home w/ hot tub & sunroom

Front Royal

Mollie S.

includes taxes & fees

3 Nov - 4 Nov

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

2 Dec - 3 Dec

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

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

Shenandoah Farms

Matt F.

includes taxes & fees

15 Nov - 16 Nov

7. Hunters Retreat with High Speed Internet

Middleburg

Kelly T.

includes taxes & fees

8 Nov - 9 Nov

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

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

Harpers Ferry

Brett D.

includes taxes & fees

5 Nov - 6 Nov

A rustic cabin with a fire pit in the yard, surrounded by trees and a wooden fence.

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

Harpers Ferry

Dawn S.

includes taxes & fees

5 Nov - 6 Nov

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

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

Apple Mountain Lake

includes taxes & fees

3 Nov - 4 Nov

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

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

Front Royal

Denise A.

includes taxes & fees

3 Nov - 4 Nov

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

12. Pool Table, Fireplace & Deck near Shenandoah Park

Front Royal

tom c.

includes taxes & fees

3 Nov - 4 Nov

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

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

Hume

includes taxes & fees

3 Nov - 4 Nov

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

14. Mountain View Bungalow in Front Royal

Front Royal

HEMANT S.

includes taxes & fees

8 Nov - 9 Nov

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.

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

Harpers Ferry

Amanda M.

includes taxes & fees

3 Nov - 4 Nov

16. Still Meadow Farm

Purcellville

Jodie J.

includes taxes & fees

9 Nov - 10 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.

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

Shannondale

Anonymous traveller

includes taxes & fees

9 Nov - 10 Nov

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

18. Leesburg Hideaway- King Bed + Private Backyard

Leesburg

Avis V.

includes taxes & fees

11 Nov - 12 Nov

An outdoor dining area with a wooden deck, a table set for four, and a view of the surrounding greenery.

19. NEW! Greek Spa - Frisbee Golf - Stonefire Pizza

Front Royal

includes taxes & fees

3 Nov - 4 Nov

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

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

Harpers Ferry

Brian S.

includes taxes & fees

3 Nov - 4 Nov

View all properties

Find holiday rentals that suit your style

Apartments

Cabins

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

Sign in

Sign up, it's free

Top Upperville Hotel Reviews

Red Roof Inn Leesburg, VA

8/10 Good

"Room was clean, staff at front desk were polite. Hotel needs some renovations it’s very outdated, but all in all was a good stay, I would stay again if needed."

Find out more about Upperville

Upperville Holiday Homes information

Number of reviews	227
Accommodation	249 Holiday Homes
Lowest Price	€195
Highest Price	€1,124

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. super cosy cottage with high speed internet!