A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

Search Apartments in Upperville

  • 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
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Upperville apartments

Property grounds

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.0 out of 10, Wonderful, (10 reviews)
"Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. "
United States
Haley M.
The price is SAR 507
SAR 1,014 total
includes taxes & fees
4 Aug - 5 Aug
Lunar Loft, with mountain views
Outdoor dining

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Markham
10.0 out of 10, Exceptional, (4 reviews)
"Such a lovely stay. The property was peaceful and relaxing, and the night sky was absolutely beautiful. We loved our time here and would happily return. Great communication (and snacks) too :)"
United States
Melissa B.
The price is SAR 815
SAR 987 total
includes taxes & fees
29 Jul - 30 Jul
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Property grounds

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Bluemont
9.8 out of 10, Exceptional, (12 reviews)
"Nice owner, great place"
United States
Leslie C.
The price is SAR 480
SAR 1,039 total
includes taxes & fees
10 Aug - 11 Aug
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Desk, iron/ironing board, WiFi (free), bed sheets

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Middleburg
9.8 out of 10, Exceptional, (27 reviews)
"The accomodations were clean and comfortable for our 1 night stay. "
United States
Claudia G.
The price is SAR 563
SAR 1,027 total
includes taxes & fees
16 Aug - 17 Aug
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
9.8 out of 10, Exceptional, (27 reviews)
"Great place to stayed "
United States
Mike F.
The price is SAR 507
SAR 878 total
includes taxes & fees
29 Jul - 30 Jul
Apple Mountain Retreat
Smart TV

Cozy 1BR Apt Minutes From Skyline Drive!!

Cozy 1BR Apt Minutes From Skyline Drive!!
Amissville
9.6 out of 10, Exceptional, (45 reviews)
"Everything was great"
United States
Lori Anne
The price is SAR 456
SAR 876 total
includes taxes & fees
29 Jul - 30 Jul
Cozy 1BR Apt Minutes From Skyline Drive!!
Interior

Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street

Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Warrenton
10.0 out of 10, Exceptional, (12 reviews)
"I love staying here! It's cozy and comfortable and in a perfect location. "
United States
Jenny D.
The price is SAR 619
SAR 997 total
includes taxes & fees
8 Aug - 9 Aug
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Outdoor dining

Historic 2-Bedroom in Old Town Warrenton, Virginia

Historic 2-Bedroom in Old Town Warrenton, Virginia
Warrenton
10.0 out of 10, Exceptional, (74 reviews)
"Great stay and utterly charming!"
United States
Jimmy
The price is SAR 619
SAR 948 total
includes taxes & fees
9 Aug - 10 Aug
Historic 2-Bedroom in Old Town Warrenton, Virginia
Exterior

Romantic African-Inspired Studio on Alpaca Farm – Under the Stars

Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
The Plains
9.8 out of 10, Exceptional, (9 reviews)
"The entire stay was nothing but exceptional. The host was very informative, knowledgeable, and helped make the stay all it can be and then some."
United States
Joe D.
The price is SAR 1,314
SAR 1,921 total
includes taxes & fees
30 Jul - 31 Jul
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
TV

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Winchester Historic District
10.0 out of 10, Exceptional, (1 review)
"The unit is very nice, exactly as described, The bed are comfortable and everything was fine. The location is excellent very near to historical sights and downtown shopping district."
United States
Timothy B.
The price is SAR 556
SAR 974 total
includes taxes & fees
29 Jul - 30 Jul
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Fridge, microwave, oven, stovetop

The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.6 out of 10, Good, (8 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
The price is SAR 349
SAR 771 total
includes taxes & fees
29 Jul - 30 Jul
The Queen of Winchester Three Bedroom with Upper Level Deck
Living area

Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is SAR 601
SAR 1,128 total
includes taxes & fees
29 Jul - 30 Jul
Morocco Loft 2BR overlooking city walking mall
Smart TV

Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard
Old Town Winchester
7.6 out of 10, Good, (4 reviews)
"You need to add some kitchen tongs Otherwise everything was fantastic!!!"
United States
Michelle K.
The price is SAR 548
SAR 965 total
includes taxes & fees
29 Jul - 30 Jul
Yellow Submarine trendy basement apt and courtyard
Coffee/tea maker, fridge, microwave, oven

Cameron Grace Brand New 1BR 1BA apt downtown Winchester

Cameron Grace Brand New 1BR 1BA apt downtown Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Very enjoyable stay right in historical Winchester. We enjoyed walking to a German restaurant for dinner and rested well. "
United States
Brad E.
The price is SAR 582
SAR 974 total
includes taxes & fees
29 Jul - 30 Jul
Cameron Grace Brand New 1BR 1BA apt downtown Winchester
Private kitchen

Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Old Town Winchester
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is SAR 732
SAR 948 total
includes taxes & fees
29 Jul - 30 Jul
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Smart TV, books

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester Historic District
8.8 out of 10, Excellent, (5 reviews)
"Loved being so close to the old town; was able to walk to a lot of places. Great to have an assigned parking spot in a lot behind the building. Enjoyed staying here a lot!"
United States
Leslie L.
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Smart TV, fireplace

Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.8 out of 10, Exceptional, (7 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is SAR 833
SAR 1,472 total
includes taxes & fees
29 Jul - 30 Jul
Scarborough Fair walk to downtown two story apt
Private kitchen

Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Old Town Winchester
The price is SAR 635
SAR 1,221 total
includes taxes & fees
31 Jul - 1 Aug
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Exterior detail

The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
7.0 out of 10, Good, (2 reviews)
"Everything went smoothly. Easy stay. Clean. Small efficiency with futon for bed."
United States
Greg A.
The price is SAR 413
SAR 757 total
includes taxes & fees
16 Aug - 17 Aug
The Stock Exchange downtown 3rd floor studio apt
Interior

Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very Good, (2 reviews)
"Small but appropriately priced."
United States
John M.
The price is SAR 413
SAR 723 total
includes taxes & fees
25 Aug - 26 Aug
Rosamond nice downtown studio apt
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

Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"."
Hyeyeon 2-night trip
Posted 15 hours ago
Lansdowne Resort and Spa

Frequently asked questions

What's it like to stay at an apartment in Upperville?
There are 8 lodging options in Upperville. Though there aren't many apartments, we can help you locate similar accommodations. When you search on Expedia, you can filter by amenities you might find in an apartment such as a kitchen. You can even filter by similar properties such as vacation homes, condos, or cabins.
How do you know if an apartment is the best choice for you?
An apartment is often more spacious than a traditional hotel room and includes a kitchen, so you can have some home-cooked meals. Apartments are ideal for families who want the conveniences of home, and also for couples who want to stay away from the tourist areas.
What's the top apartment for a stay in Upperville?
Below are some of the top apartments in the area to choose from: Apple Mountain Retreat: Located in Linden, 13.2 mi/21.2 km from the heart of Upperville. Includes free WiFi, private patios, and fireplaces. Access to onsite laundry facilities is available on site. Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues: Located in Leesburg, 14.8 mi/23.8 km away. Includes free WiFi, private patios, and sofa beds. Access to onsite laundry facilities is available on site. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!: 20.1 mi/32.3 km away in Winchester. WonderClock House downtown vintage duplex w/ porches, steps to Handley Library: It's located in Winchester, 20.2 mi/32.4 km from Upperville. Includes fireplaces and Smart TVs.
What can I expect from the weather in Upperville?
Though weather is just one factor, it can really affect your travel plans, especially when you're planning an extended stay in Upperville. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 37°F. Average annual precipitation for Upperville is 44 inches.
What are the must-see places to visit in Upperville?
Explore the area and family-friendly sights such as Dinosaur Land, or get out into nature at a spot like Upperville Park. In the larger area, you'll find Sky Meadows State Park and Delaplane Cellars.
What's the best way to get to and around Upperville?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Washington Dulles Intl. Airport (IAD), which is located 23.7 mi (38.2 km) away from the city center. Otherwise, look for flights into Manassas, VA (MNZ-Manassas Regional), which is 27.3 mi (44 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.