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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Upperville vacation 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

Mountain Escape: Hottub + Fireplace + WiFi +PetsOK
Front Royal
The price is ￥22,019
￥60,718 total
includes taxes & fees
Sep 29 - Sep 30
Mountain Escape: Hottub + Fireplace + WiFi +PetsOK
A two-story house with a porch, surrounded by trees and grass.

2. 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)
"If we managed to do everything, sing, dance, play, we loved the comfortable place for us"
United States
Erick U.
The price is ￥29,726
￥59,559 total
includes taxes & fees
Oct 7 - Oct 8
1910 Farmhouse on 6 Acres • VA Wine Country

3. DC Wine Country Farmhouse | 5 Peaceful Acres

DC Wine Country Farmhouse | 5 Peaceful Acres
Loudoun County
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay. House is beautiful and clean and owner was highly responsive. "
United States
Michele B.
The price is ￥35,388
￥68,238 total
includes taxes & fees
Sep 29 - Sep 30
DC Wine Country Farmhouse | 5 Peaceful Acres
A deck with outdoor seating and a lake view.

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

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
10.0 out of 10, Exceptional, (11 reviews)
"Had a wonderful stay here. Shaun was an excellent host with easy communication. Peaceful location with a lake! Convenient to Harper’s Ferry. "
United States
Liz P.
The price is ￥23,592
￥57,061 total
includes taxes & fees
Oct 26 - Oct 27
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
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

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (21 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!"
United States
Denise B.
The price is ￥47,970
￥87,141 total
includes taxes & fees
Oct 5 - Oct 6
Spacious Modern Home on Middleburg Horse Farm

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

Mountain Views w/Hot Tub, 95” TV & Trail Access
Shenandoah Farms
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Joshua J.
The price is ￥31,645
￥52,337 total
includes taxes & fees
Sep 29 - Sep 30
Mountain Views w/Hot Tub, 95” TV & Trail Access
A single-story brick building with a front porch, a picnic table, and a barbecue grill.

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

Shenandoah River House | 3BR - Private Dock - Pets
Front Royal
The price is ￥22,019
￥61,759 total
includes taxes & fees
Sep 29 - Sep 30
Shenandoah River House | 3BR - Private Dock - Pets
A wooden deck with white railings and a covered porch area.

8. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (43 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is ￥21,233
￥34,136 total
includes taxes & fees
Sep 29 - Sep 30
Mountain View Bungalow in Front Royal
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!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! So peaceful and beautiful property. Andrea is a great host!"
United States
Erin C.
The price is ￥22,762
￥57,011 total
includes taxes & fees
Oct 12 - Oct 13
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
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 Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (38 reviews)
"Clean sweet place to stay and relax. Couldn't have been nicer."
United States
Avis V.
The price is ￥22,648
￥47,750 total
includes taxes & fees
Oct 7 - Oct 8
Leesburg Hideaway- King Bed + Private Backyard
A skateboard with the word 'Ringo' on it, mounted on a blue wall.

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

A-Frame Soak and Cedar near Skyline Drive and Wineries
Front Royal
The price is ￥31,418
￥58,827 total
includes taxes & fees
Oct 14 - Oct 15
A-Frame Soak and Cedar near Skyline Drive and Wineries
A garden with a wooden swing set and a circular seating area.

12. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (51 reviews)
"We enjoyed our stay here. The property was lovely and the house was nicely stocked and decorated. We will definitely stay again when in the area!"
United States
Marsha N.
The price is ￥22,648
￥45,798 total
includes taxes & fees
Oct 5 - Oct 6
Newly renovated Farm cottage with Mountain views
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!

Riverview Retreat - Pool, Hot Tub, and Mtn Views!
Harpers Ferry
10.0 out of 10, Exceptional, (6 reviews)
"Had a fantastic time and everything was great! Highly recommend this spot for a vacation if you’re headed for Harper’s ferry."
United States
James A.
The price is ￥15,728
￥61,975 total
includes taxes & fees
Sep 30 - Oct 1
Riverview Retreat - Pool, Hot Tub, and Mtn Views!
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

Golfers' Paradise: 3 Courses Nearby + Pool Table
Front Royal
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Crystal H.
The price is ￥40,421
￥91,252 total
includes taxes & fees
Oct 12 - Oct 13
Golfers' Paradise: 3 Courses Nearby + Pool Table
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

Stone Cabin on Valley View: Fire Pit + Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful scenery! Beautiful home! Wonderful hosts!"
United States
Brian S.
The price is ￥28,546
￥59,448 total
includes taxes & fees
Oct 6 - Oct 7
Stone Cabin on Valley View: Fire Pit + Hot Tub
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

Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge
Shannondale
10.0 out of 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!"
United States
Anonymous traveler
The price is ￥37,197
￥72,535 total
includes taxes & fees
Sep 29 - Sep 30
Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge
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

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Harpers Ferry
7.4 out of 10, Good, (28 reviews)
"The inside was well done and clean. Even though the neighbors are close, they were quiet. My husband and I were able to relax in a comfortable setting."
United States
Melissa H.
The price is ￥21,516
￥50,333 total
includes taxes & fees
Oct 26 - Oct 27
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
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

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Harpers Ferry
10.0 out of 10, Exceptional, (20 reviews)
"Overall good property- close location to all attractions"
United States
Trisha P.
The price is ￥25,165
￥61,862 total
includes taxes & fees
Sep 29 - Sep 30
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
A bar area with wooden beams, hanging light fixtures, and a bar counter with stools.

19. Main Street USA -- Walk to Everything

Main Street USA -- Walk to Everything
Purcellville
9.8 out of 10, Exceptional, (11 reviews)
"The property was great! Very clean and walkable to town. We had a wonderful time and Joe was great to work with! We would absolutely love to stay here again!"
United States
melissa b.
The price is ￥74,551
￥116,966 total
includes taxes & fees
Oct 4 - Oct 5
Main Street USA -- Walk to Everything
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

Farmhouse Retreat Sleeps 6, Yard for Tents, Near River + C&O Canal
Harpers Ferry
7.2 out of 10, Good, (17 reviews)
"We had a great stay. Good location, close to Leesburg, Frederick, and Harper's Ferry center.The house was as described."
United States
Gwenaelle M.
The price is ￥21,091
￥47,215 total
includes taxes & fees
Oct 13 - Oct 14
Farmhouse Retreat Sleeps 6, Yard for Tents, Near River + C&O Canal
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

8/10 Good
"The parking lot has no control. Everyone parked how ever they want to park. The some of the trailers parked and blocked 6 parking space"
Suat Serol and Ruya Mahdum 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Winchester

Find out more about Upperville

Upperville Vacation Homes information

Number of reviews
222
Accommodation
249 Vacation Homes
Lowest Price
￥34,136
Highest Price
￥116,966