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

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Upperville cottages

A stone house with a chimney, surrounded by a well-maintained lawn and trees.

1. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (66 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
The price is €349
includes taxes & fees
30 Sept - 1 Oct
18th Century Stone Cottage minutes from historic Middleburg
A modern building with large windows, a deck, and a stone wall.

2. Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!
Harpers Ferry
9.8 out of 10, Exceptional, (28 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
The price is €303
includes taxes & fees
24 Sept - 25 Sept
Woodsy Retreat with a Hot Tub and Seasonal Views!
A hot tub on an outdoor deck with a view of trees and hills.

3. Mountain View Cottage | Hot Tub & Game Room

Mountain View Cottage | Hot Tub & Game Room
Front Royal
9.8 out of 10, Exceptional, (17 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is €670
includes taxes & fees
7 Oct - 8 Oct
Mountain View Cottage | Hot Tub & Game Room
A covered deck with a table and chairs, overlooking a river and autumn foliage.

4. Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (28 reviews)
"With bedrooms and sitting rooms on 3 floors, our 3-generation family enjoyed having space to gather together as well as space for time apart. The decks allowed for additional places to enjoy the beautiful surroundings. Lake access was great for swimming and kayaking."
United States
Lindy K.
The price is €454
includes taxes & fees
7 Oct - 8 Oct
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
A covered outdoor area with a fire pit, seating, and a view of the landscape.

5. Mountain View Cottage with Hot Tub and River Views

Mountain View Cottage with Hot Tub and River Views
Front Royal
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay and certainly return. Our group was 2 couples and 2 children.Everyone had enough space to be comfortable. The view is beautiful so we enjoyed our time at the house. While in the area, we visited Skyline Caverns and the Shenandoah River. I did have a challenging time getting Door Dash to the house. After 30 minutes of seeing the driver in the neighborhood we got in the car to track down the driver. Her cell service was poor so we were unable to communicate. If I ordered...
United States
MaryBeth C.
The price is €615
includes taxes & fees
29 Sept - 30 Sept
Mountain View Cottage with Hot Tub and River Views
A covered outdoor area with a fire pit, seating, and a view of the landscape.

6. Mountaintop Cottage | Private Hot Tub

Mountaintop Cottage | Private Hot Tub
Front Royal
9.8 out of 10, Exceptional, (27 reviews)
"Excellent location and amazing reviews. Would definitely plan to arrive while it’s light out for the first time as the road does get a little rough at the top but we did all make it in 2WD vehicles"
United States
Sara Z.
The price is €607
includes taxes & fees
27 Sept - 28 Sept
Mountaintop Cottage | Private Hot Tub
A hot tub under a wooden pergola with a grassy yard and trees in the background.

7. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
9.6 out of 10, Exceptional, (39 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
The price is €678
includes taxes & fees
22 Oct - 23 Oct
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
A hot tub with a view of a forested landscape during sunset.

8. Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (27 reviews)
"The property was so nice with a beautiful view. We had a great time! Highly recommend this property."
United States
Anonymous traveller
The price is €380
includes taxes & fees
12 Oct - 13 Oct
Cottage w/ Hot Tub and 100-Mile Valley Views!
A covered outdoor area with a hot tub, wooden benches, and a view of a snowy landscape with trees and a fence.

9. The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
10.0 out of 10, Exceptional, (26 reviews)
"Very relaxing stay! Clean hot tub!! "
United States
Mara H.
The price is €354
includes taxes & fees
24 Sept - 25 Sept
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

10. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (16 reviews)
"Unique and adorable little place on the river. Perfectly clean and comfortable. We would definitely book again!"
United States
Hailey
The price is €375
includes taxes & fees
24 Sept - 25 Sept
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A single-story house with a porch, a stone pathway leading to the entrance, and a clear sky.

11. Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Front Royal
9.6 out of 10, Exceptional, (17 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is €201
includes taxes & fees
29 Sept - 30 Sept
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
A stone house with a white picket fence, a front porch, and potted plants.

12. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
3.0 star property
Leesburg's Old and Historic District
The price is €593
includes taxes & fees
22 Oct - 23 Oct
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
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

10/10 Excellent
"Been there at least once a year for past dozen years. Great location. My only complaint was the lightening was dim at the pool during my last visit bur that's a minor issue."
John 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Winchester

Find out more about Upperville

Upperville Cottages information

Number of reviews
238
Accommodation
99 Cottages
Lowest Price
€201
Highest Price
€678

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