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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Upperville cottages

Property grounds

1. Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA

Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
Front Royal
The price is AED 772
AED 920 total
includes taxes & fees
9 Aug - 10 Aug
Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
Terrace/patio

2. 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, (24 reviews)
"GREAT stay…loved the location, the hot tub, the amenities, and the host."
United States
Domenic E.
The price is AED 826
AED 1,453 total
includes taxes & fees
17 Aug - 18 Aug
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Exterior

3. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (63 reviews)
"Loved out stay! "
United States
Emilee
The price is AED 1,010
AED 1,446 total
includes taxes & fees
6 Aug - 7 Aug
18th Century Stone Cottage minutes from historic Middleburg
Outdoor spa tub

4. 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, (26 reviews)
"This was a lovely rental in a breathtaking location. My whole family gasped at that view as we came over the hill and down the driveway! Could not have asked for a more picturesque front yard, and the sunsets from the hot tub were epic. The house was very clean, comfortable, and well appointed, with two generously sized bath tubs inside and comfy beds. Great game selection (although some of the contents were mixed into the wrong boxes), and we enjoyed the ping pong table too. Communication...
United States
Lauren P.
The price is AED 404
AED 1,452 total
includes taxes & fees
10 Aug - 11 Aug
Cottage w/ Hot Tub and 100-Mile Valley Views!
Exterior

5. 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, (26 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
The price is AED 367
AED 1,259 total
includes taxes & fees
18 Aug - 19 Aug
Woodsy Retreat with a Hot Tub and Seasonal Views!
Outdoor dining

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

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (26 reviews)
"Great house! The view was amazing. Having extra kayaks was great. If you plan to use the lake, plan for 10 per person per day, that was an added expense for a family of six! "
United States
Amy H.
The price is AED 951
AED 2,452 total
includes taxes & fees
11 Aug - 12 Aug
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Terrace/patio

7. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (39 reviews)
"Excellent property for a relaxing getaway. Very clean. Host very responsive."
United States
Brad C.
The price is AED 687
AED 1,785 total
includes taxes & fees
31 Aug - 1 Sep
Peaceful Lakefront Cottage with Mountain Views!
Outdoor spa tub

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

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
10.0 out of 10, Exceptional, (36 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
The price is AED 1,305
AED 2,639 total
includes taxes & fees
3 Sep - 4 Sep
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Terrace/patio

9. Apple Mountain House | Hot Tub | Game Room

Apple Mountain House | Hot Tub | Game Room
Front Royal
9.6 out of 10, Exceptional, (15 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is AED 724
AED 1,985 total
includes taxes & fees
1 Sep - 2 Sep
Apple Mountain House | Hot Tub | Game Room
Terrace/patio

10. All-Inclusive 4BR | Mountain Views | Hot Tub

All-Inclusive 4BR | Mountain Views | Hot Tub
Front Royal
The price is AED 738
AED 1,989 total
includes taxes & fees
30 Aug - 31 Aug
All-Inclusive 4BR | Mountain Views | Hot Tub
Terrace/patio

11. The VUE | Mountaintop 4BR | Hot Tub & Views

The VUE | Mountaintop 4BR | Hot Tub & Views
Front Royal
10.0 out of 10, Exceptional, (23 reviews)
"Amazing location! Clean and well kept! Wonderful experience!"
United States
Kaylyn K.
The price is AED 1,241
AED 2,402 total
includes taxes & fees
17 Aug - 18 Aug
The VUE | Mountaintop 4BR | Hot Tub & Views
Outdoor spa tub

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

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (15 reviews)
"Unique and adorable little place on the river. Perfectly clean and comfortable. We would definitely book again!"
United States
Hailey
The price is AED 1,074
AED 1,601 total
includes taxes & fees
6 Aug - 7 Aug
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Exterior

13. 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 AED 545
AED 816 total
includes taxes & fees
9 Aug - 10 Aug
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"A convenient stay close to Rt 81 in western Virginia. Clean , comfortable and reasonable in a shopping center with quick access to the highway. Located in a shopping center with a number of food options including an Aldi and an Alamo Draft house movie theatre. The was clean , well appointed and everything worked !"
sharon 1-night trip
Posted less than an hour ago
Comfort Inn & Suites Winchester

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