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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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, (64 reviews)
"Loved out stay! "
United States
Emilee
The price is CA $382
CA $551 total
includes taxes & fees
Aug 30 - Aug 31
18th Century Stone Cottage minutes from historic Middleburg
A hot tub on an outdoor deck with a view of trees and hills.

2. Mountain View Cottage | Hot Tub & Game Room

Mountain View Cottage | 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 CA $256
CA $725 total
includes taxes & fees
Sep 2 - Sep 3
Mountain View Cottage | Hot Tub & Game Room
A covered outdoor area with a fire pit, seating, and a view of the landscape.

3. Mountain-View Cottage | Hot Tub & River Views

Mountain-View Cottage | Hot Tub & River Views
Front Royal
The price is CA $244
CA $710 total
includes taxes & fees
Aug 30 - Aug 31
Mountain-View Cottage | Hot Tub & River Views

4. 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 CA $291
CA $348 total
includes taxes & fees
Sep 9 - Sep 10
Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
A hot tub with a view of a forested landscape during sunset.

5. 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)
"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 CA $139
CA $530 total
includes taxes & fees
Aug 31 - Sep 1
Cottage w/ Hot Tub and 100-Mile Valley Views!
A modern building with large windows, a deck, and a stone wall.

6. 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 CA $139
CA $477 total
includes taxes & fees
Sep 2 - Sep 3
Woodsy Retreat with a Hot Tub and Seasonal Views!
A hot tub on a deck with a view of a lake and forest.

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 CA $194
CA $642 total
includes taxes & fees
Sep 14 - Sep 15
Peaceful Lakefront Cottage with Mountain Views!
A covered outdoor area with a fire pit, seating, and a view of the landscape.

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

The VUE | Mountaintop 4BR | Hot Tub & Views
Front Royal
10.0 out of 10, Exceptional, (24 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 CA $468
CA $906 total
includes taxes & fees
Aug 30 - Aug 31
The VUE | Mountaintop 4BR | Hot Tub & Views
A hot tub under a wooden pergola with a grassy yard and trees in the background.

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

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
9.8 out of 10, Exceptional, (37 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
The price is CA $399
CA $895 total
includes taxes & fees
Sep 3 - Sep 4
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
A covered deck with a table and chairs, overlooking a river and autumn foliage.

10. 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 CA $297
CA $835 total
includes taxes & fees
Sep 3 - Sep 4
Art Docko - Lakefront Artist Retreat w/ 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 CA $205
CA $308 total
includes taxes & fees
Aug 30 - Aug 31
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

12. Charming Garden Cottage in Historic Warrenton - Walk to Restaurants + Shops

Charming Garden Cottage in Historic Warrenton - Walk to Restaurants + Shops
Warrenton
The price is CA $149
CA $348 total
includes taxes & fees
Sep 5 - Sep 6
Charming Garden Cottage in Historic Warrenton - Walk to Restaurants + Shops
A covered outdoor area with a hot tub, wooden benches, and a view of a snowy landscape with trees and a fence.

13. 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 CA $311
CA $547 total
includes taxes & fees
Aug 30 - Aug 31
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.

14. 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 CA $405
CA $600 total
includes taxes & fees
Aug 30 - Aug 31
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A stone house with a white picket fence, a front porch, and potted plants.

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

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (6 reviews)
"Great location to town of leesburg and can walk to restaurants and shops. Big kitchen and nice outdoor space. "
United States
Corky F.
The price is CA $470
CA $964 total
includes taxes & fees
Sep 3 - Sep 4
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
A stone house with a white picket fence, a front porch, and potted plants.

16. 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 CA $563
CA $939 total
includes taxes & fees
Sep 3 - Sep 4
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
A two-story house with a front porch, a covered entryway, and a small front yard.

17. 'thomson Farm' Classic Home < 10 Mi to Vineyards!

'thomson Farm' Classic Home < 10 Mi to Vineyards!
3.0 star property
Leesburg
The price is CA $1,925
CA $2,968 total
includes taxes & fees
Sep 20 - Sep 21
'thomson Farm' Classic Home < 10 Mi to Vineyards!
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

Hampton Inn Front Royal

Hampton Inn Front Royal

10/10 Excellent
"they gave us room smelled like hamster or rabit.When we asked to change they changed."
Gurpreet 1-night trip
Posted 5 hours ago
Hampton Inn Front Royal

Find out more about Upperville

Upperville Cottages information

Number of reviews
295
Accommodation
101 Cottages
Lowest Price
CA $308
Highest Price
CA $2,968

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