Upperville Vacation Homes

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

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Our top choices for Upperville holiday homes

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

1. Mountain Escape: Hottub + Fireplace + WiFi +PetsOK

Front Royal

HK$3,028 total

includes taxes & fees

29 Sept - 30 Sept

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

2. 1910 Farmhouse on 6 Acres • VA Wine Country

Marshall

Erick U.

HK$2,970 total

includes taxes & fees

7 Oct - 8 Oct

3. DC Wine Country Farmhouse | 5 Peaceful Acres

Loudoun County

Michele B.

HK$3,403 total

includes taxes & fees

28 Sept - 29 Sept

A deck with outdoor seating and a lake view.

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

Harpers Ferry

Liz P.

HK$1,747 total

includes taxes & fees

28 Sept - 29 Sept

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.

HK$4,435 total

includes taxes & fees

5 Oct - 6 Oct

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.

HK$3,051 total

includes taxes & fees

30 Sept - 1 Oct

A single-story brick building with a front porch, a picnic table, and a barbecue grill.

7. Shenandoah River House | 3BR - Private Dock - Pets

Front Royal

HK$3,080 total

includes taxes & fees

28 Sept - 29 Sept

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

8. Mountain View Bungalow in Front Royal

Front Royal

HEMANT S.

HK$1,728 total

includes taxes & fees

5 Oct - 6 Oct

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.

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

Harpers Ferry

Erin C.

HK$2,599 total

includes taxes & fees

28 Sept - 29 Sept

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

10. Leesburg Hideaway- King Bed + Private Backyard

Leesburg

Avis V.

HK$2,300 total

includes taxes & fees

27 Sept - 28 Sept

A bedroom with a sloped ceiling, a ceiling fan, a bed with multiple pillows, a bedside table, and a window with a view of greenery.

11. A-Frame Soak and Cedar near Skyline Drive and Wineries

Front Royal

HK$3,049 total

includes taxes & fees

14 Oct - 15 Oct

A garden with a wooden swing set and a circular seating area.

12. Newly renovated Farm cottage with Mountain views

Strasburg

Marsha N.

HK$2,284 total

includes taxes & fees

27 Sept - 28 Sept

A modern kitchen with a large island, white cabinets, and a dining area with a bench and chairs.

13. Riverview Retreat - Pool, Hot Tub, and Mtn Views!

Harpers Ferry

James A.

HK$3,091 total

includes taxes & fees

30 Sept - 1 Oct

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

14. Golfers' Paradise: 3 Courses Nearby + Pool Table

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.

HK$4,818 total

includes taxes & fees

14 Oct - 15 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.

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

Harpers Ferry

Brian S.

HK$2,964 total

includes taxes & fees

6 Oct - 7 Oct

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

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

Shannondale

Anonymous traveller

HK$3,841 total

includes taxes & fees

29 Sept - 30 Sept

A sign for Antietam National Battlefield, part of the National Park Service, with a stone wall and flowers in the foreground.

17. Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

Harpers Ferry

Melissa H.

HK$2,733 total

includes taxes & fees

8 Oct - 9 Oct

A bedroom with a large bed, a bench, a chair, a nightstand, and a wall with decorative plates.

18. Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

Harpers Ferry

Trisha P.

HK$3,085 total

includes taxes & fees

28 Sept - 29 Sept

A bar area with wooden beams, hanging light fixtures, and a bar counter with stools.

19. Main Street USA -- Walk to Everything

Purcellville

melissa b.

HK$5,832 total

includes taxes & fees

4 Oct - 5 Oct

A covered porch with a table and chairs, a number 64 on the wall, and a small garden area.

20. Farmhouse Retreat Sleeps 6, Yard for Tents, Near River + C&O Canal

Harpers Ferry

Gwenaelle M.

HK$2,486 total

includes taxes & fees

27 Oct - 28 Oct

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Top Upperville Hotel Reviews

TRU By Hilton Winchester

10/10 Excellent

"Overnight stay on a road trip. Wonderful front desk staff, friendly & professional. Room was in excellent condition. Very comfy bed, clean bathroom with great towels, delicious breakfast buffet with plenty of options. Definitely on the list to stay again!"

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"Good bed, nice size room, desk clerk was very helpful in getting us on the non-highway side of the property (which was then very quiet). Breakfast OK, lots of restaurants around the property and a movie theatre. Good location for Winchester"

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