Welcome sign to Upperville Virginia in Fauquier County.

Search Upperville Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

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 ￥24,023
￥36,492 total
includes taxes & fees
Jun 30 - Jul 1
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 ￥23,295
￥71,352 total
includes taxes & fees
Jul 1 - Jul 2
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 ￥16,155
￥57,922 total
includes taxes & fees
Jul 6 - Jul 7
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 ￥33,441
￥95,770 total
includes taxes & fees
Jun 30 - Jul 1
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 ￥39,095
￥94,977 total
includes taxes & fees
Jul 22 - Jul 23
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 ￥44,426
￥64,484 total
includes taxes & fees
Jul 2 - Jul 3
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 ￥16,155
￥55,198 total
includes taxes & fees
Jun 29 - Jun 30
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 ￥36,398
￥64,363 total
includes taxes & fees
Jul 7 - Jul 8
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 ￥47,318
￥69,590 total
includes taxes & fees
Jun 28 - Jun 29
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 ￥38,663
￥94,749 total
includes taxes & fees
Jul 26 - Jul 27
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 ￥54,604
￥104,597 total
includes taxes & fees
Jul 15 - Jul 16
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upperville Hotel Reviews

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Front desk staff very friendly and helpful. Would stay here again . Very clean . Breakfast was average but well maintained and food was hot ,friendly staff in breakfast room. Close to 81 and easy to find"
Elizabeth 1-night trip
Posted 1 hour ago
Comfort Inn & Suites Winchester

Find out more about Upperville

Upperville Cottages information

Number of reviews
225
Accommodation
98 Cottages
Lowest Price
￥36,492
Highest Price
￥104,597

Frequently asked questions

Why book your cottage in Upperville with Expedia?
Reserving a cottage in Upperville is as simple as clicking on your travel dates and selecting your ideal place for a vacation in the outdoors. From ritzy retreats to affordable stays and cottages that come with amenities like laundry facilities, Expedia has something for all styles. As for the best offers around? We've got them too!
How can I find cheap cottages in Upperville?
A good way to uncover cheap cottages in Upperville is with Expedia's filter tool. Narrow your search by budget, star rating and amenities to access awesome rates in just a few clicks.