Search Apartments in Upperville

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 77 Apartments in Upperville with updated reviews, rates, and availability.

Historic apartment in Old Town Warrenton, Virginia
Outdoor dining

Historic apartment in Old Town Warrenton, Virginia

9.8 out of 10, Exceptional, (40)
"Host was amazing!"
The price is AED 621
AED 939 total
includes taxes & fees
6 May - 7 May
Historic apartment in Old Town Warrenton, Virginia
Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues
Fridge, microwave, oven, stovetop

Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues

10.0 out of 10, Exceptional, (77)
"We stay often. Consistently great place to stay while visiting family and friends in the leesburg area. "
Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues
The Queen of Winchester Three Bedroom with Upper Level Deck
Private kitchen

The Queen of Winchester Three Bedroom with Upper Level Deck

9.4 out of 10, Exceptional, (3)
"Enjoyed our stay. 5 minute drive to historic downtown. Property owner was accommodating and easy to communicate with. Very nice stay while working in Winchester. "
The price is AED 246
AED 643 total
includes taxes & fees
4 May - 5 May
The Queen of Winchester Three Bedroom with Upper Level Deck
Front Royal Retreat on 3 Acres w/ Mtn Views!
Fridge, microwave, oven, dishwasher

Front Royal Retreat on 3 Acres w/ Mtn Views!

2.0 star property
8.8 out of 10, Excellent, (3)
"House and overall property was very clean and we really enjoyed it and the spring water was amazing"
Front Royal Retreat on 3 Acres w/ Mtn Views!
Cozy 1BR Apt Minutes From Skyline Drive!!
Fridge, microwave, oven, stovetop

Cozy 1BR Apt Minutes From Skyline Drive!!

9.6 out of 10, Exceptional, (28)
"Excellent stay! Great property. Looking gorward to a return stay."
The price is AED 496
AED 917 total
includes taxes & fees
4 May - 5 May
Cozy 1BR Apt Minutes From Skyline Drive!!
Nostalgia Lane in the heart of the city
Miscellaneous

Nostalgia Lane in the heart of the city

9.4 out of 10, Exceptional, (8)
"We enjoyed the small town feel of Winchester. Our stay here was the cherry on top. Such a beautiful place with so much personality, we will definitely be back!!!!"
The price is AED 731
AED 1,286 total
includes taxes & fees
4 May - 5 May
Nostalgia Lane in the heart of the city
Cozy English Basement Apt quiet but close to downtown
Miscellaneous

Cozy English Basement Apt quiet but close to downtown

9.6 out of 10, Exceptional, (7)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
The price is AED 331
AED 603 total
includes taxes & fees
5 May - 6 May
Cozy English Basement Apt quiet but close to downtown
Charming 2-bedroom 2nd floor apartment with WiFi, AC in lovely Charles Town
Smart TV

Charming 2-bedroom 2nd floor apartment with WiFi, AC in lovely Charles Town

9.0 out of 10, Wonderful, (2)
"Susan was a great host. The location was convenient and the accomodation comfortable. "
The price is AED 551
AED 834 total
includes taxes & fees
4 May - 5 May
Charming 2-bedroom 2nd floor apartment with WiFi, AC in lovely Charles Town
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Exterior

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

9.0 out of 10, Wonderful, (4)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
The price is AED 753
AED 1,361 total
includes taxes & fees
4 May - 5 May
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Charming Front Royal Retreat ~ 1 Mi to River!
Microwave, stovetop, coffee/tea maker, toaster

Charming Front Royal Retreat ~ 1 Mi to River!

10.0 out of 10, Exceptional, (1)
"We arrived in the afternoon before a festival. Main street was closed, but we were still able to access the parking. Everything was clean, and we had a comfortable stay. There were restaurants and entertainment right outside. The only thing not in easy walking distance was a drugstore/CVS. I highly recommend staying at this location."
Charming Front Royal Retreat ~ 1 Mi to River!
Morocco Loft 2BR overlooking city walking mall
Living area

Morocco Loft 2BR overlooking city walking mall

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great property with all the comforts of home"
Morocco Loft 2BR overlooking city walking mall
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Desk, iron/ironing board, free WiFi, bed sheets

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

9.8 out of 10, Exceptional, (14)
"Nice , quiet and clean place to stay with my two little dogs."
The price is AED 551
AED 1,001 total
includes taxes & fees
4 May - 5 May
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Apple Mountain Retreat
Property grounds

Apple Mountain Retreat

10.0 out of 10, Exceptional, (13)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is AED 588
AED 972 total
includes taxes & fees
4 May - 5 May
Apple Mountain Retreat
Cozy studio close to Skyline Drive, Hiking, and Main Street.
Private kitchen

Cozy studio close to Skyline Drive, Hiking, and Main Street.

8.0 out of 10, Very Good, (1)
"Spent the day in the park , very convenient "
The price is AED 624
AED 785 total
includes taxes & fees
4 May - 5 May
Cozy studio close to Skyline Drive, Hiking, and Main Street.
Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg
Interior

Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg

10.0 out of 10, Exceptional, (6)
"The location of this adorable cottage can’t be beat! Just minutes (by car) to downtown Middleburg. It’s perfect for a couple. "
Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg
The Blue Door steps from Handley Library
Miscellaneous

The Blue Door steps from Handley Library

2.0 star property
6.0 out of 10, (1)
"While the owner could not have been nicer, VRBO dropped the ball. We did not get check in information, though the host provided it directly on hour after check-in time.The host needs to check in with the cleaners and visit the property. I say this as a landlord. We had one washcloth for two guests, no coffee or tea service, no tissues, no dish rag. The place looks a little run down and needs a refresh. Doors were broken, bathroom racks about to fall off the wall, and one soap dispenser was...
The price is AED 422
AED 707 total
includes taxes & fees
4 May - 5 May
The Blue Door steps from Handley Library
Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly
Living area

Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly

2.0 out of 10, (1)
"For a new listing to VRBO, the property did not meet our expectations. Check in time on app was incorrect delaying our activities. Communication with owner was delay and resulted in conversation with VRBO. Pictures of apartment were not accurate to the unit. The property is in a "Corporate Apartment" complex but apartment is nowhere near the standards of a corporate apartment. The cable remote didn't work. TV in bedroom was plugged in but no cable hook up. Windowsill and door frame damaged by...
Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly
Private apartment on a beautiful private farm!
1 bedroom, WiFi

Private apartment on a beautiful private farm!

10.0 out of 10, Exceptional, (2)
"This little farm condo was absolutely perfect for our overnight stay. In fact, I wish we had the opportunity to stay longer. It was lovely to wake up and see chickens and other animals as well as hear the dogs barking. The view of the mountains was also lovely! We will definitely think of staying here again next time we visit our friends!"
The price is AED 551
AED 1,064 total
includes taxes & fees
5 May - 6 May
Private apartment on a beautiful private farm!
Alpaca Farm Studio Apartment, Newly decorated
Exterior

Alpaca Farm Studio Apartment, Newly decorated

9.8 out of 10, Exceptional, (9)
"A beautiful spot. Exactly as described!"
The price is AED 1,286
AED 1,829 total
includes taxes & fees
4 May - 5 May
Alpaca Farm Studio Apartment, Newly decorated
The Stock Exchange downtown 3rd floor studio apt
Microwave, oven, stovetop

The Stock Exchange downtown 3rd floor studio apt

2.0 star property
6.0 out of 10, (1)
The price is AED 364
AED 682 total
includes taxes & fees
29 May - 30 May
The Stock Exchange downtown 3rd floor 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.
Don't see what you're looking for?
See all available properties in Upperville
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Upperville

18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (40)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is AED 1,010
AED 1,439 total
includes taxes & fees
11 May - 12 May
18th Century Stone Cottage minutes from historic Middleburg
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (83)
"The cabin is beautiful and tucked away in the trees. Amazing colors this time of year and was such a great little getaway. Highly recommend staying here!"
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
Outdoor dining

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

9.2 out of 10, Wonderful, (13)
"Week with elderly family members and this home was a good spot to rest and relax. Upon arrival, house was neat and clean. Well stocked with cooking items. Nice layout. Good central locations for day trip options. Overall I would recommend this home. "
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
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.

Frequently asked questions

What's it like to stay at an apartment in Upperville?
There are 5 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: Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues: Located in Leesburg, 14.8 mi/23.8 km from the heart of Upperville. Includes free WiFi, private patios, and sofa beds. Access to onsite laundry facilities is available on site. Cozy studio close to Skyline Drive, Hiking, and Main Street.: It’s located in Front Royal, 17.4 mi/28.1 km away. Historic apartment in Old Town Warrenton, Virginia: Located 19.7 mi/31.7 km away in Warrenton. Free WiFi, private patios, and separate dining areas are included. Access to onsite laundry facilities is available on site. WonderClock House downtown vintage duplex w/ porches, steps to Handley Library: It’s situated in Winchester, 20.2 mi/32.4 km from Upperville.
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 Great Country Farms, 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.