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Our top choices for Upperville cottages
1. 18th Century Stone Cottage minutes from historic Middleburg
18th Century Stone Cottage minutes from historic MiddleburgMiddleburg
10.0 out of 10, Exceptional, (68 reviews)
"A quaint cottage in a beautiful location!"
Mary H.
$366 nightly
The price is $393
Nov 15 - Nov 16
Total with taxes and fees
2. Mountain View Cottage with Hot Tub and River Views
Mountain View Cottage with Hot Tub and River ViewsFront 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...
MaryBeth C.
$445 nightly
The price is $491
Dec 1 - Dec 2
Total with taxes and fees
3. Mountain View Cottage | Hot Tub & Game Room
Mountain View Cottage | Hot Tub & Game RoomFront Royal
9.8 out of 10, Exceptional, (17 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
Katia R.
$607 nightly
The price is $669
Nov 15 - Nov 16
Total with taxes and fees
4. Mountaintop Cottage | Private Hot Tub
Mountaintop Cottage | Private Hot TubFront Royal
9.8 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay, house was beautiful and clean. Coffee in the morning with the deer was awesome. Love the neighborhood cat Luna."
Kevin D.
$547 nightly
The price is $603
Nov 11 - Nov 12
Total with taxes and fees
5. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-FiBoyce
9.4 out of 10, Exceptional, (40 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
Felice N.
$606 nightly
The price is $668
Nov 23 - Nov 24
Total with taxes and fees
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, (29 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."
Lindy K.
$423 nightly
The price is $471
Nov 18 - Nov 19
Total with taxes and fees
7. 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, (29 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."
Rebecca N.
$348 nightly
The price is $389
Nov 12 - Nov 13
Total with taxes and fees
8. Peaceful Lakefront Cottage with Mountain Views!
Peaceful Lakefront Cottage with Mountain Views!Harpers Ferry
9.8 out of 10, Exceptional, (42 reviews)
"The property was absolutely beautiful. The view of the lake was so pretty. Communication with the host was wonderful very informative. Very cozy and the house was beautiful inside."
Tara G.
$381 nightly
The price is $426
Nov 18 - Nov 19
Total with taxes and fees
9. 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, (29 reviews)
"My husband and I went for a short trip. The communication was great and the house was perfect! We spent most of our time in the hot tub checking out the amazing view."
Keri L.
$364 nightly
The price is $406
Nov 12 - Nov 13
Total with taxes and fees
10. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Riverfront! Shenandoah River! Sleeps 4! New Hot TubFront 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!"
Hailey
$373 nightly
The price is $415
Nov 11 - Nov 12
Total with taxes and fees
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, (27 reviews)
"Fun place to stay!!!"
Theresa R.
$329 nightly
The price is $375
Nov 11 - Nov 12
Total with taxes and fees
12. 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 ViewFront Royal
9.0 out of 10, Wonderful, (18 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
Jake M.
$188 nightly
The price is $207
Nov 11 - Nov 12
Total with taxes and fees
13. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
Cottage w/ Furnished Patio & Garden: Dtwn LeesburgLeesburg's Old and Historic District
9.8 out of 10, Exceptional, (7 reviews)
"Great location to town of leesburg and can walk to restaurants and shops. Big kitchen and nice outdoor space. "
Corky F.
$573 nightly
The price is $659
Nov 22 - Nov 23
Total with taxes and fees
14. Renovated 3B/3B Home | Downtown | Private Fire Pit
Renovated 3B/3B Home | Downtown | Private Fire PitLeesburg's Old and Historic District
9.8 out of 10, Exceptional, (44 reviews)
"Great location, would stay again."
Eric D S.
$497 nightly
The price is $554
Nov 11 - Nov 12
Total with taxes and fees
15. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
Cottage w/ Furnished Patio & Garden: Dtwn LeesburgLeesburg's Old and Historic District
$591 nightly
The price is $679
Nov 22 - Nov 23
Total with taxes and fees
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.
Learn more about Upperville
Hunt country elegance shines at the historic Upperville Horse Show, America's oldest running exhibition where equestrians compete each June. Wander through the quaint village to discover stone buildings, antique shops, and Sky Meadows State Park's hiking trails nearby in Paris.
Top reviews in Upperville
Goodstone Inn & Restaurant
Goodstone Inn & RestaurantMiddleburg
10/10 Excellent
We were looking for peace and quiet. This was definitely the place.
Adrian
