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

Historic apartment in Old Town Warrenton, Virginia

9.8 out of 10, Exceptional, (37)
"Great location and comfortable place."
The price is AED 606
AED 915 total
includes taxes & fees
17 Apr - 18 Apr
Historic apartment in Old Town Warrenton, Virginia

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

10.0 out of 10, Exceptional, (75)
"Mary and I have stayed at quite a few VRBO's and this was by far the best, from the high quality of the accommodations, cleanliness, and attention to detail. I received a birthday card, bottle of wine, birthday cupcakes, there were fresh flowers in every room, the bedding was amazing, a generous supply of snacks and drinks and the place was tastefully decorated for the Easter season. "
Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues

The Queen of Winchester Three Bedroom with Upper Level Deck

10.0 out of 10, Exceptional, (2)
"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
17 Apr - 18 Apr
The Queen of Winchester Three Bedroom with Upper Level Deck

Front Royal Retreat on 3 Acres w/ Mtn Views!

2.0 star property
10.0 out of 10, Exceptional, (2)
"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!!

9.6 out of 10, Exceptional, (28)
"Property is short drive from family and our favorite place to stay when visiting the area. Hosts are incredibly accommodating and it's a pet friendly property!"
The price is AED 496
AED 913 total
includes taxes & fees
17 Apr - 18 Apr
Cozy 1BR Apt Minutes From Skyline Drive!!

Nostalgia Lane in the heart of the city

9.0 out of 10, Wonderful, (6)
"The apartment has an eclectic layout with great charm. Very clean and perfectly situated to Old Town. "
The price is AED 731
AED 1,298 total
includes taxes & fees
20 Apr - 21 Apr
Nostalgia Lane in the heart of the city

Cozy English Basement Apt quiet but close to downtown

9.4 out of 10, Exceptional, (6)
"Very cute place to stay at a perfect location to the little historic district of Winchester. Bed was comfortable but very small futon. We are tall people so it was not quite long enough for us. Bathroom was extremely small, doable for us but if we were bigger people it would be difficult to get into that space. Water pressure for sink was poor, shower was just okay. Quaint place with a friendly, engaged owner. We would go back just for the amazing location!"
The price is AED 331
AED 603 total
includes taxes & fees
20 Apr - 21 Apr
Cozy English Basement Apt quiet but close to downtown

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 845 total
includes taxes & fees
17 Apr - 18 Apr
Charming 2-bedroom 2nd floor apartment with WiFi, AC in lovely Charles Town

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

9.0 out of 10, Wonderful, (4)
"We really like staying walking distance from the Historic District in Winchester and this was a great home base to do so. The whole process was seemless and easy. I will most likley try to come back for my conference next year. The place is clean and comfortable. Fun times "
The price is AED 753
AED 1,353 total
includes taxes & fees
17 Apr - 18 Apr
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

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

2.0 star property
10.0 out of 10, Exceptional, (2)
"Love the location, availability of parking, and the loft was very comfortable and had everything we needed."
Morocco Loft 2BR overlooking city walking mall

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

9.8 out of 10, Exceptional, (14)
"Great two days at the farm. Quiet, clean, and friendly hosts. :) "
The price is AED 551
AED 1,005 total
includes taxes & fees
20 Apr - 21 Apr
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

Apple Mountain Retreat

10.0 out of 10, Exceptional, (12)
"We enjoyed our stay! The amenities were better than advertised, and you can tell the owner put a lot of effort into making it an enjoyable experience."
The price is AED 588
AED 972 total
includes taxes & fees
20 Apr - 21 Apr
Apple Mountain Retreat

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

The price is AED 624
AED 777 total
includes taxes & fees
18 Apr - 19 Apr
Cozy studio close to Skyline Drive, Hiking, and Main Street.

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

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
17 Apr - 18 Apr
The Blue Door steps from Handley Library

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!

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 1,059 total
includes taxes & fees
17 Apr - 18 Apr
Private apartment on a beautiful private farm!

Alpaca Farm Studio Apartment, Newly decorated

9.8 out of 10, Exceptional, (9)
"This was, without a doubt, one of the best places we have ever stayed. The attention to detail, the quality of the furnishings, the charm of Mary, is all unmatched. We will be returning!"
The price is AED 1,286
AED 1,868 total
includes taxes & fees
17 Apr - 18 Apr
Alpaca Farm Studio Apartment, Newly decorated

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
1 May - 2 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.
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Other property types in Upperville

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (84)
"This beautiful cabin has everything you need for a wonderful stay. My husband and I stayed here for our 44th anniversary while visiting local wineries. It was a perfect location."
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

Cozy Mountain Cabin w/ Steam Shower! Great for Couples.

10.0 out of 10, Exceptional, (61)
"It's the perfect place to stay if you're going to HF but want some distance from people/a view of the mountains. Really nice property. We'd stay again! Thanks!"
The price is AED 624
AED 1,325 total
includes taxes & fees
21 Apr - 22 Apr
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (38)
"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities. "
The price is AED 1,010
AED 1,466 total
includes taxes & fees
17 Apr - 18 Apr
18th Century Stone Cottage minutes from historic Middleburg
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?
Listed below are some of the favorite apartments in the area to choose from: Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues: Located 14.8 mi/23.8 km away in Leesburg. Free WiFi, private patios, and sofa beds are included. Historic apartment in Old Town Warrenton, Virginia: It’s situated in Warrenton, 19.7 mi/31.7 km away. Includes free WiFi, private patios, and separate dining areas. Nostalgia Lane in the heart of the city: 20 mi/32.2 km away in Winchester. 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.