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 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 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.
$369 nightly
The price is $396
Oct 12 - Oct 13
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg
A two-story house with a wooden deck, surrounded by lush greenery.

2. 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
$253 nightly
The price is $268
Oct 27 - Oct 28
Total with taxes and fees
Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
A covered outdoor area with a fire pit, seating, and a view of the landscape.

3. 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.
$601 nightly
The price is $663
Oct 6 - Oct 7
Total with taxes and fees
Mountain View Cottage with Hot Tub and River Views
A hot tub on an outdoor deck with a view of trees and hills.

4. 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.
$620 nightly
The price is $684
Oct 7 - Oct 8
Total with taxes and fees
Mountain View Cottage | Hot Tub & Game Room
A covered outdoor area with a fire pit, seating, and a view of the landscape.

5. 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.
$564 nightly
The price is $622
Oct 5 - Oct 6
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.

6. 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.
$706 nightly
The price is $778
Oct 22 - Oct 23
Total with taxes and fees
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
A covered deck with a table and chairs, overlooking a river and autumn foliage.

7. 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.
$443 nightly
The price is $493
Oct 7 - Oct 8
Total with taxes and fees
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
A modern building with large windows, a deck, and a stone wall.

8. 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)
"Property was a great location for all we wanted to do during our vacation. The beach area was the perfect retreat for some relaxation after long days of hiking. Area is beautiful, house was comfortable (slept like a baby), and we had a great stay. Would definitely stay again."
United States
Rebecca N.
$306 nightly
The price is $341
Oct 21 - Oct 22
Total with taxes and fees
Woodsy Retreat with a Hot Tub and Seasonal Views!
A hot tub on a deck with a view of a lake and forest.

9. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (42 reviews)
"Clean house. Host was able to accessible. Hot tub worked and clean. Kitchen had everything we needed. Great place to stay and relax"
United States
Lisa h.
$488 nightly
The price is $543
Oct 19 - Oct 20
Total with taxes and fees
Peaceful Lakefront Cottage with Mountain Views!
A hot tub with a view of a forested landscape during sunset.

10. 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
$414 nightly
The price is $461
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.

11. 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)
"Fun place to stay!!!"
United States
Theresa R.
$347 nightly
The price is $396
Oct 4 - Oct 5
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.

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, (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
Oct 4 - Oct 5
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.

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.
$205 nightly
The price is $226
Oct 4 - Oct 5
Total with taxes and fees
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
A two-story house with a porch and a front door.

14. Renovated 3B/3B Home | Downtown | Private Fire Pit

Renovated 3B/3B Home | Downtown | Private Fire Pit
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (42 reviews)
"Great location, would stay again."
United States
Eric D S.
$446 nightly
The price is $499
Nov 2 - Nov 3
Total with taxes and fees
Renovated 3B/3B Home | Downtown | Private Fire Pit
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.
$599 nightly
The price is $689
Oct 22 - Oct 23
Total with taxes and fees
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
$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

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

8/10 Good
"Well sized clean room with comfortable, hot showers and large fridge. Well, engineered room layout from electrical connections to lighting and HVAC controls but wished fridge had freezer option."
Lisa 1-night trip
Posted 11 hours ago
Microtel Inn & Suites by Wyndham Winchester

Find out more about Upperville

Upperville Cottages information

Number of reviews
286
Accommodation
103 Cottages
Lowest Price
$226
Highest Price
$778

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