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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Upperville cottages

Exterior

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 HK$2,157
HK$3,131 total
includes taxes & fees
16 Aug - 17 Aug
18th Century Stone Cottage minutes from historic Middleburg
Terrace/patio

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

All-Inclusive 4BR | Mountain Views | Hot Tub
Front Royal
The price is HK$1,553
HK$4,257 total
includes taxes & fees
24 Aug - 25 Aug
All-Inclusive 4BR | Mountain Views | Hot Tub
Exterior

3. 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 HK$785
HK$2,706 total
includes taxes & fees
12 Aug - 13 Aug
Woodsy Retreat with a Hot Tub and Seasonal Views!
Terrace/patio

4. 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 HK$2,652
HK$5,140 total
includes taxes & fees
24 Aug - 25 Aug
The VUE | Mountaintop 4BR | Hot Tub & Views
Outdoor spa tub

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)
"We enjoyed our stay and the property was exactly what we were looking for in a mountain getaway peaceful, private, and immersed in the woods with beautiful views and a relaxing atmosphere.The home was clean, quiet, and met our needs well for a restful escape. The hosts were communicative and supportive, although we did not need to reach out during our stay.The driveway is definitely mountain-style, so guests should come prepared and be mindful of the vehicle they bring, but the secluded setting...
United States
B S.
The price is HK$808
HK$3,040 total
includes taxes & fees
19 Aug - 20 Aug
Cottage w/ Hot Tub and 100-Mile Valley Views!
Terrace/patio

6. 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 HK$1,436
HK$4,076 total
includes taxes & fees
17 Aug - 18 Aug
Apple Mountain House | Hot Tub | Game Room
Outdoor spa tub

7. 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 HK$2,990
HK$5,998 total
includes taxes & fees
3 Sept - 4 Sept
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Outdoor spa tub

8. 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 HK$2,295
HK$3,418 total
includes taxes & fees
24 Aug - 25 Aug
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Terrace/patio

9. 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 HK$1,412
HK$4,098 total
includes taxes & fees
31 Aug - 1 Sept
Peaceful Lakefront Cottage with Mountain Views!
Outdoor dining

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, (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 HK$1,930
HK$5,093 total
includes taxes & fees
19 Aug - 20 Aug
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Coffee/tea maker, fridge, microwave, oven

11. Royal Heritage Home @ Historic Leesburg

Royal Heritage Home @ Historic Leesburg
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (42 reviews)
"Great location, would stay again."
United States
Eric D S.
The price is HK$1,812
HK$3,828 total
includes taxes & fees
12 Aug - 13 Aug
Royal Heritage Home @ Historic Leesburg
Terrace/patio

12. 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 HK$1,765
HK$3,121 total
includes taxes & fees
17 Aug - 18 Aug
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
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 HK$1,165
HK$1,752 total
includes taxes & fees
13 Aug - 14 Aug
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Exterior

14. 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 HK$1,648
HK$1,990 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
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
"The property was the cleanest hotel we have ever stayed at. The staff were friendly and breakfast was delicious. I highly recommend this hotel."
Kathleen 1-night trip
Posted 2 hours ago
TRU By Hilton Winchester

Find out more about Upperville

Upperville Cottages information

Number of reviews
249
Accommodation
98 Cottages
Lowest Price
HK$1,752
Highest Price
HK$5,998

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