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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Upperville cottages

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 NZ$394
includes taxes & fees
30 June - 1 July
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
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, (24 reviews)
"Great view, very secluded"
United States
Matt s.
The price is NZ$776
includes taxes & fees
1 July - 2 July
Cottage w/ Hot Tub and 100-Mile Valley Views!
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, (23 reviews)
"The house had wonderful spaces to use for our weekend getaway!"
United States
Jessame P.
The price is NZ$638
includes taxes & fees
6 July - 7 July
Lake View Retreat - Cottage Near a Peaceful Lake!
Outdoor dining

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)
"The host was prompt with answering any inquiries. The house was well stocked. Great area to visit."
United States
Ellen B.
The price is NZ$1,033
includes taxes & fees
30 June - 1 July
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Terrace/patio

All-Inclusive 4BR | Mountain Views | Hot Tub

All-Inclusive 4BR | Mountain Views | Hot Tub
Front Royal
The price is NZ$1,004
includes taxes & fees
21 July - 22 July
All-Inclusive 4BR | Mountain Views | Hot Tub
Exterior

18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (62 reviews)
"Loved out stay! "
United States
Emilee
The price is NZ$699
includes taxes & fees
2 July - 3 July
18th Century Stone Cottage minutes from historic Middleburg
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 NZ$597
includes taxes & fees
29 June - 30 June
Woodsy Retreat with a Hot Tub and Seasonal Views!
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
10.0 out of 10, Exceptional, (22 reviews)
"GREAT stay…loved the location, the hot tub, the amenities, and the host."
United States
Domenic E.
The price is NZ$696
includes taxes & fees
6 July - 7 July
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
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 NZ$753
includes taxes & fees
28 June - 29 June
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Terrace/patio

Apple Mountain House | Hot Tub | Game Room

Apple Mountain House | Hot Tub | Game Room
Front Royal
9.6 out of 10, Exceptional, (14 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is NZ$1,004
includes taxes & fees
20 July - 21 July
Apple Mountain House | Hot Tub | Game Room
Terrace/patio

The VUE | Mountaintop 4BR | Hot Tub & Views

The VUE | Mountaintop 4BR | Hot Tub & Views
Front Royal
10.0 out of 10, Exceptional, (23 reviews)
"We had such a great experience staying at The Vue! The home was incredibly well cared for, and everything matched the listing perfectly which made planning our trip so much easier. Check-in was smooth and stress-free, and the host did a fantastic job providing all the information we needed ahead of time. It truly felt like a 10/10 stay, and we’d love to come back!"
United States
David S.
The price is NZ$1,150
includes taxes & fees
5 July - 6 July
The VUE | Mountaintop 4BR | Hot Tub & Views
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

Spark by Hilton Winchester

Spark by Hilton Winchester

8/10 Good
"Overall great experience - with that said their computer system wasnt working right. I was charged for the room twice (over and above the already charged payment from Expedia) and also a $100 security deposit. I brought it up the next day and it was immediately corrected. Nice hotel, good local, and friendly staff."
Robert 1-night trip
Posted 4 hours ago
Spark by Hilton Winchester

Find out more about Upperville

Upperville Cottages information

Number of reviews
225
Accommodation
94 Cottages
Lowest Price
NZ$394
Highest Price
NZ$1,150