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Compare 65 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 SAR 746
SAR 1,326 total
includes taxes & fees
18 Feb - 19 Feb
Nostalgia Lane in the heart of the city

Historic apartment in Old Town Warrenton, Virginia

10.0 out of 10, Exceptional, (33)
"This was our second stay at this lovely VRBO and we had yet another wonderful experience. Bill is such a gracious host and made sure everything was just right for our visit. We won’t stay anywhere else when visiting our family in the Warrenton area and can’t wait to be back soon! Thank you Bill!"
The price is SAR 619
SAR 926 total
includes taxes & fees
22 Feb - 23 Feb
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

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

The price is SAR 638
SAR 810 total
includes taxes & fees
18 Feb - 19 Feb
Cozy studio close to Skyline Drive, Hiking, and Main Street.

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 SAR 259
SAR 648 total
includes taxes & fees
26 Feb - 27 Feb
The Queen of Winchester Three Bedroom with Upper Level Deck

Cozy English Basement Apt quiet but close to downtown

10.0 out of 10, Exceptional, (3)
"My dog and I enjoyed our snowy winter getaway in Michele’s cozy basement! Everything was as stated and what we needed. I liked being able to walk to downtown Winchester or hop in my car.. I would return!"
The price is SAR 338
SAR 616 total
includes taxes & fees
18 Feb - 19 Feb
Cozy English Basement Apt quiet but close to downtown

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

National at Loudoun

3.0 star property
6.8 out of 10, (6)
"Great stay fast communication "
National at Loudoun

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 SAR 563
SAR 1,005 total
includes taxes & fees
2 Mar - 3 Mar
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 SAR 563
SAR 943 total
includes taxes & fees
18 Feb - 19 Feb
Apple Mountain Retreat

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!

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.

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 SAR 431
SAR 727 total
includes taxes & fees
18 Feb - 19 Feb
The Blue Door steps from Handley Library

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

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 SAR 506
SAR 932 total
includes taxes & fees
18 Feb - 19 Feb
Cozy 1BR Apt Minutes From Skyline Drive!!

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

Relaxing Blue Ridge Mountain Getaway w/ Tesla Charger + Porch Area

9.0 out of 10, Wonderful, (4)
"When our roommates got to be a bit too much, we decided to escape over a long weekend. Picked this vrbo due to its (relative) proximity to hiking and its kitchen, and it was PERFECT. The hosts were amazingly nice and thoughtful. We brought our own baking ingredients and pans, but the kitchen had every kitchen utensil and pan you could want.Truly a lovely oasis to bake some cinnamon rolls in the mountains during a snowstorm.Thank you!"
Relaxing Blue Ridge Mountain Getaway w/ Tesla Charger + Porch Area

Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard

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

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 SAR 1,313
SAR 1,920 total
includes taxes & fees
18 Feb - 19 Feb
Alpaca Farm Studio Apartment, Newly decorated
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, (36)
"Adorable cottage. Well appointef"
The price is SAR 1,031
SAR 1,469 total
includes taxes & fees
18 Feb - 19 Feb
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

Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!

10.0 out of 10, Exceptional, (79)
"My husband and I had a lovely stay in this cabin for Thanksgiving. We had everything we needed to cook our Thanksgiving meal, stay cozy, and enjoy the views around the cabin. Thank you!"
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!
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: Nostalgia Lane in the heart of the city: Located 20 mi/32.2 km away in Winchester. 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. Apple Mountain Retreat: 13.2 mi/21.2 km away in Linden. Free WiFi, private patios, and Smart TVs are included. Cozy studio close to Skyline Drive, Hiking, and Main Street.: It’s situated in Front Royal, 17.4 mi/28.1 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?
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 Barrel Oak Winery.
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.