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Compare 62 Apartments in Upperville with updated reviews, rates, and availability.

Nostalgia Lane in the heart of the city

9.6 out of 10, Exceptional, (4)
"We need overnight accommodations for our daughter’s surprise proposal. We checked into the VRBO and we were stunned! We walked around in silence taking in all of the charm, beauty and uniqueness of this home. This is a clean place with a very comfortable mattress! It is a fascinating place and we just loved it!! The host was very gracious and communicative - we wanted for nothing!! Five Starts "
The price is AED 731
AED 1,273 total
includes taxes & fees
24 Jan - 25 Jan
Nostalgia Lane in the heart of the city

Historic apartment in Old Town Warrenton, Virginia

10.0 out of 10, Exceptional, (31)
"An autumn cozy retreat for my family. Walking distance to the farmer's market, shops, and restaurants made for wonderful use of our downtime between wedding festivities. "
The price is AED 606
AED 911 total
includes taxes & fees
24 Jan - 25 Jan
Historic apartment in Old Town Warrenton, Virginia

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 Queen of Winchester Three Bedroom with Upper Level Deck

10.0 out of 10, Exceptional, (1)
"If you want to be in the town and have quick access to everything, this is the place for you."
The price is AED 290
AED 742 total
includes taxes & fees
3 Feb - 4 Feb
The Queen of Winchester Three Bedroom with Upper Level Deck

National at Loudoun

3.0 star property
7.6 out of 10, Good, (5)
"Great stay fast communication "
National at Loudoun

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

The price is AED 500
AED 638 total
includes taxes & fees
24 Jan - 25 Jan
Cozy studio close to Skyline Drive, Hiking, and Main Street.

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

Cozy English Basement Apt quiet but close to downtown

10.0 out of 10, Exceptional, (2)
"Downtown Winchester is charming, and the property was an easy walk from downtown (though in a safe suburban neighborhood). The property itself was just as advertised. I was able to cook meals there; the bed was comfortable; it was much nicer and more varied than a hotel room."
The price is AED 331
AED 603 total
includes taxes & fees
26 Jan - 27 Jan
Cozy English Basement Apt quiet but close to downtown

New Wine Horse Country 10 Acre Lux Retreat amid historic sites. Stunning Views!

10.0 out of 10, Exceptional, (22)
"We had a wonderful stay. Everything was exactly as described. Very clean, all necessities were great, linens and towels were very nice. The grounds are large with beautiful views. Very close to restaurants, wineries and breweries. The host was very helpful and responded within minutes. "
New Wine Horse Country 10 Acre Lux Retreat amid historic sites. Stunning Views!

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

10.0 out of 10, Exceptional, (71)
"This is the best experience I have ever had with any VRBO property. The guest suite was immaculate, comfortable and beautifully appointed. And Nancy and Al could not have been more accommodating. I cannot recommend it highly enough. I will definitely be back. "
Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues

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

9.8 out of 10, Exceptional, (13)
"lovely room, great shower, so wuiet and peaceful, great environs (sheep! donkey! cheese!), such a nice stay!"
The price is AED 551
AED 992 total
includes taxes & fees
27 Jan - 28 Jan
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

Cozy 1BR Apt Minutes From Skyline Drive!!

9.6 out of 10, Exceptional, (25)
"Great place to stay with my pup. When my phone died, the owner and granddaughter were super helpful in writing down return directions. Thanks!"
The price is AED 496
AED 909 total
includes taxes & fees
24 Jan - 25 Jan
Cozy 1BR Apt Minutes From Skyline Drive!!

This apartment is a 1 bedroom(s), 1 bathrooms, located in Leesburg, VA.

10.0 out of 10, Exceptional, (1)
"We had a great stay! Place was clean and easy to find everything. If we come back that way we will definitely look Sheila’s place up again 😊"
This apartment is a 1 bedroom(s), 1 bathrooms, located in Leesburg, VA.

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 1,880 total
includes taxes & fees
26 Jan - 27 Jan
Alpaca Farm Studio Apartment, Newly decorated

The Outpost Suite 2- A Curated Farmhouse Suite

6.6 out of 10, (7)
"The property is a bit off its prime... the deck in the back is not like it appears in the picture. Not a terrible property, but a bit run down. I did appreciate that we were the only ones there and quietness was good for a great nights sleep. Great areas to walk the dog. The property manager was very nice and helpful. Greeted us when we arrived and made sure we got in okay."
The Outpost Suite 2- A Curated Farmhouse Suite

Magnificent Middleburg Getaway: 2BR w Bucolic Views, Solar Power, & Nearby Shops

10.0 out of 10, Exceptional, (1)
"We really enjoyed our experience with this stay. The place was laid out excellent. It was clean, spacious, and technology enabled - which is very important for us to be able to both work and entertain. The location is quiet and just off the path to town. The owner was welcoming and supportive of our stay. We would stay there again and recommend it to others looking for the same experience."
Magnificent Middleburg Getaway: 2BR w Bucolic Views, Solar Power, & Nearby Shops

Lofts for weekly rentals! 2 miles from historic downtown.

Lofts for weekly rentals! 2 miles from historic downtown.

The Outpost Suite 3 - Whimsical Farmhouse Retreat

7.8 out of 10, Good, (9)
"The property includes three separate units within one house, and we experienced several issues during our stay. We arrived at night and found no lights to guide us, making it difficult to locate where we were staying. The main house door was unlocked, and the back door was wide open, which raised concerns about security. Assuming the main house was our accommodation, we entered and walked through it. However, with the back door open, we were worried someone might be inside who shouldn’t...
The Outpost Suite 3 - Whimsical Farmhouse Retreat

Trout's Loft 2 Bedroom, Historic Downtown Front Royal, VA

Trout's Loft 2 Bedroom, Historic Downtown Front Royal, VA

Scarborough Fair walk to downtown two story apt

9.4 out of 10, Exceptional, (3)
"The location of this property is fabulous giving you lots of things to do. However this is an older home and as such it only has one bathroom. Michelle was great too communicate with. She also sent a long some information on things to do in the area."
Scarborough Fair walk to downtown two story 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

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (35)
"We absolutely loved this little cottage. It's a great location near Middleburg, tucked back in the woods. It's got everything you need for a peaceful retreat. A perfect place to curl up in front of the fire with a book. The host was so welcoming and easy to work with. We'll definitely be back!"
The price is AED 1,010
AED 1,446 total
includes taxes & fees
26 Jan - 27 Jan
18th Century Stone Cottage minutes from historic Middleburg

Breathtaking views with an indoor private pool, come escape with us

9.8 out of 10, Exceptional, (244)
"Our group had an amazing stay at the Bear Chase Manor! The house has great common space areas and the pool was a huge hit with everyone. We also loved the convenience of being next to the brewery along with the incredible views of nature. Can't wait to have the opportunity to stay here again!"
Breathtaking views with an indoor private pool, come escape with us

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (40)
"Lots of space for everyone, excellent pool and hot tub"
Charles Town Home w/ Private Pool & Hot Tub
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: 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. New Wine Horse Country 10 Acre Lux Retreat amid historic sites. Stunning Views!: It’s situated in Leesburg, 15.5 mi/24.9 km away. Includes free WiFi, private patios, and sofa beds. Nostalgia Lane in the heart of the city: 20 mi/32.2 km away in Winchester. Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg: It’s located in Middleburg, 8.8 mi/14.1 km from Upperville. Includes free WiFi, private patios, 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?
Sky Meadows State Park and Upperville Park are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Delaplane Cellars and RdV Vineyards.
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.