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

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.
$370 nightly
The price is $397
Sep 30 - Oct 1
Total with taxes and fees
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.
$386 nightly
The price is $429
Sep 27 - Sep 28
Total with taxes and fees
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.
$651 nightly
The price is $718
Sep 29 - Sep 30
Total with taxes and fees
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.
$440 nightly
The price is $491
Sep 30 - Oct 1
Total with taxes and fees
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.
$646 nightly
The price is $713
Sep 28 - Sep 29
Total with taxes and fees
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.
$629 nightly
The price is $694
Sep 27 - Sep 28
Total with taxes and fees
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.
$670 nightly
The price is $739
Oct 22 - Oct 23
Total with taxes and fees
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 traveler
$383 nightly
The price is $426
Oct 12 - Oct 13
Total with taxes and fees
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.
$347 nightly
The price is $396
Sep 27 - Sep 28
Total with taxes and fees
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
$392 nightly
The price is $436
Sep 29 - Sep 30
Total with taxes and fees
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.
$205 nightly
The price is $226
Sep 29 - Sep 30
Total with taxes and fees
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
$591 nightly
The price is $679
Oct 22 - Oct 23
Total with taxes and fees
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

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"Great Location & Customer Service"
CONSTANTIN 1-night trip
Posted less than an hour ago
TRU By Hilton Winchester

Find out more about Upperville

Upperville Cottages information

Number of reviews
238
Accommodation
98 Cottages
Lowest Price
$226
Highest Price
$739

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