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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Upperville cottages

Exterior

Apple Mountain House • Hot Tub • Game Room

Apple Mountain House • Hot Tub • Game Room
Front Royal
9.8 out of 10, Exceptional, (12 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is HK$1,323
HK$3,203 total
includes taxes & fees
13 May - 14 May
Apple Mountain House • Hot Tub • Game Room
Exterior

Lake View Retreat - Cottage Near a Peaceful Lake!

Lake View Retreat - Cottage Near a Peaceful Lake!
Harpers Ferry
9.6 out of 10, Exceptional, (22 reviews)
"The house had wonderful spaces to use for our weekend getaway!"
United States
Jessame P.
The price is HK$783
HK$2,732 total
includes taxes & fees
25 May - 26 May
Lake View Retreat - Cottage Near a Peaceful Lake!
Terrace/patio

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.8 out of 10, Exceptional, (16 reviews)
"Property was beautiful, and the hot tub was amazing! We will definitely book again!"
United States
KasiLyn D.
The price is HK$1,761
HK$3,097 total
includes taxes & fees
13 May - 14 May
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Outdoor spa tub

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, (22 reviews)
"Great view, very secluded"
United States
Matt s.
The price is HK$783
HK$2,946 total
includes taxes & fees
27 May - 28 May
Cottage w/ Hot Tub and 100-Mile Valley Views!
Exterior

18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (59 reviews)
"Loved out stay! "
United States
Emilee
The price is HK$2,153
HK$3,108 total
includes taxes & fees
10 Jun - 11 Jun
18th Century Stone Cottage minutes from historic Middleburg
Outdoor spa tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (14 reviews)
"Excellent place to stay. Shelly is an excellent host. Nice location "
United States
Lisa H.
The price is HK$2,290
HK$3,411 total
includes taxes & fees
21 May - 22 May
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Property grounds

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (25 reviews)
"The host was prompt with answering any inquiries. The house was well stocked. Great area to visit."
United States
Ellen B.
The price is HK$1,730
HK$4,704 total
includes taxes & fees
1 Jun - 2 Jun
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Exterior

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$1,163
HK$1,740 total
includes taxes & fees
13 May - 14 May
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Outdoor spa tub

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, (35 reviews)
"A very spacious and well equipped home to get away from it all; but, also convenient to Winchester for a night out. The fenced in areas for dogs were lovely."
United States
David A.
The price is HK$3,064
HK$5,961 total
includes taxes & fees
7 Jun - 8 Jun
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Terrace/patio

Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
10.0 out of 10, Exceptional, (35 reviews)
"The house is lovely and clean, and has a great view of the lake. We reserved during the winter and couldn’t use the lake but would love to return in warmer weather to be able to use more of the outdoors. "
United States
Cathy W.
The price is HK$1,112
HK$3,362 total
includes taxes & fees
19 May - 20 May
Peaceful Lakefront Cottage with Mountain Views!
Exterior

The VUE • Mountaintop 4BR • Hot Tub & Views

The VUE • Mountaintop 4BR • Hot Tub & Views
Front Royal
10.0 out of 10, Exceptional, (21 reviews)
"Good communication from the host, very beautiful home with amazing scenery! Our group had a great time!"
United States
Devin P.
The price is HK$2,646
HK$4,649 total
includes taxes & fees
20 May - 21 May
The VUE • Mountaintop 4BR • Hot Tub & Views
Exterior

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$783
HK$2,584 total
includes taxes & fees
25 May - 26 May
Woodsy Retreat with a Hot Tub and Seasonal Views!
Terrace/patio

All-Inclusive 4BR • Mountain Views • Hot Tub

All-Inclusive 4BR • Mountain Views • Hot Tub
Front Royal
The price is HK$1,440
HK$3,352 total
includes taxes & fees
21 May - 22 May
All-Inclusive 4BR • Mountain Views • Hot Tub
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
"Property felt safe and convenient during travel. Well lit, clean exterior. Gentlemen at the front desk was professional, polite and quick with check in. Entrances to property were convenient to elevators etc. Very clean lobby and room. We did not partake in the breakfast but it looked clean and well stocked. Very nice stay. Definitely recommend."
Cassandra 1-night trip
Posted 2 hours ago
TRU By Hilton Winchester

Find out more about Upperville

Upperville Cottages information

Number of reviews
278
Accommodation
90 Cottages
Lowest Price
HK$1,740
Highest Price
HK$5,961

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