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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

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

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, (83)
"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
Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg
Interior

Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg

9.8 out of 10, Exceptional, (7)
"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
Cozy studio close to Skyline Drive, Hiking, and Main Street.
Private kitchen

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

9.0 out of 10, Wonderful, (2)
"Spent the day in the park , very convenient "
The price is AED 624
AED 785 total
includes taxes & fees
5 Jun - 6 Jun
Cozy studio close to Skyline Drive, Hiking, and Main Street.
Historic apartment in Old Town Warrenton, Virginia
Outdoor dining

Historic apartment in Old Town Warrenton, Virginia

9.8 out of 10, Exceptional, (43)
"Host was amazing!"
The price is AED 559
AED 855 total
includes taxes & fees
9 Jun - 10 Jun
Historic apartment in Old Town Warrenton, Virginia
Charming Loft In Winchester Va, Furnished and all Inclusive
Living area

Charming Loft In Winchester Va, Furnished and all Inclusive

Charming Loft In Winchester Va, Furnished and all Inclusive
The Queen of Winchester Three Bedroom with Upper Level Deck
Private kitchen

The Queen of Winchester Three Bedroom with Upper Level Deck

8.4 out of 10, Very Good, (5)
"If you want to be in the town and have quick access to everything, this is the place for you."
The Queen of Winchester Three Bedroom with Upper Level Deck
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Exterior

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

8.8 out of 10, Excellent, (5)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
The price is AED 621
AED 1,190 total
includes taxes & fees
9 Jun - 10 Jun
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
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
8.4 out of 10, Very Good, (6)
"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!
Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg
Fridge, microwave, oven, stovetop

Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg

10.0 out of 10, Exceptional, (1)
"Didn’t know what to expect, but regardless I was blown away. The place is VERY well furnished with everything you need to enjoy your stay. It was the perfect place to come back home to and relax after a long day. The owner was also amazing, she left a few chocolates and a welcome note. She was also an amazing communicator, I didn’t need too many things, but the things I did need, she accommodated instantly. 10/10, this place is phenomenal "
The price is AED 404
AED 1,246 total
includes taxes & fees
9 Jun - 10 Jun
Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg
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 1,833 total
includes taxes & fees
5 Jun - 6 Jun
Alpaca Farm Studio Apartment, Newly decorated
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)
"I love this property! An oasis for me and my dog. Jimmie is a great host, as well!"
The price is AED 446
AED 849 total
includes taxes & fees
5 Jun - 6 Jun
Cozy 1BR Apt Minutes From Skyline Drive!!
National at Loudoun
Apartment, 2 Bedrooms | Private kitchen | Full-size fridge, microwave, oven, stovetop

National at Loudoun

3.0 star property
6.8 out of 10, (6)
"Great stay fast communication "
National at Loudoun
Berryville Bliss: Basement Apartment in welcoming Berryville
Outdoor dining

Berryville Bliss: Basement Apartment in welcoming Berryville

10.0 out of 10, Exceptional, (1)
"Very comfortable, clean, and spacious. Safe, easy to navigate neighborhood. I was there for two nights for a Trackdaze event at Summit Point. It’s a great place to stay."
Berryville Bliss: Basement Apartment in welcoming Berryville
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
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 529
AED 895 total
includes taxes & fees
8 Jun - 9 Jun
Apple Mountain Retreat
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, (15)
"Nice , quiet and clean place to stay with my two little dogs."
The price is AED 551
AED 1,005 total
includes taxes & fees
5 Jun - 6 Jun
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
New - The Skyline Flat
Smart TV, stereo

New - The Skyline Flat

10.0 out of 10, Exceptional, (1)
"We had an absolutely wonderful stay! The location was perfect as it was just minutes from the Appalachian Trail and close to downtown, which made exploring and dining out super convenient. The home itself was beautifully furnished, spotless, and incredibly comfortable. We slept so well and didn’t have any significant street noise. A special shoutout to our host, who went above and beyond to make sure we were well situated. They were incredibly responsive, kind, and even gave us an excellent...
New - The Skyline Flat
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
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
28 Jun - 29 Jun
Cozy English Basement Apt quiet but close to downtown
Nostalgia Lane in the heart of the city
Miscellaneous

Nostalgia Lane in the heart of the city

9.0 out of 10, Wonderful, (9)
"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 1,282 total
includes taxes & fees
9 Jun - 10 Jun
Nostalgia Lane in the heart of the city
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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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: Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg: Situated in Middleburg, 8.8 mi/14.1 km from the heart of Upperville. Includes free WiFi, private patios, and Smart TVs. Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg: Located 19.2 mi/30.9 km away in Leesburg. Free WiFi, private patios, and Smart TVs are included. Onsite laundry facilities and a sauna are 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. Apple Mountain Retreat: Located 13.2 mi/21.2 km away in Linden. Free WiFi, private patios, and Smart TVs are included. 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 from Upperville. Includes free WiFi, private patios, and sofa beds. Access to onsite laundry facilities is available on site.
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 Virginia River Trips, 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.