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Compare 54 Apartments in Upperville with updated reviews, rates, and availability.

Cozy 1BR Apt Minutes From Skyline Drive!!

9.6 out of 10, Exceptional, (24)
"This property is exactly as pictured and described. The host was accommodating and responsive. If I am back in the area I would stay here again. The location to many area attractions is perfect."
The price is AED 496
AED 917 total
includes taxes & fees
24 Dec - 25 Dec
Cozy 1BR Apt Minutes From Skyline Drive!!

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

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!

Nostalgia Lane in the heart of the city

9.4 out of 10, Exceptional, (3)
"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
24 Dec - 25 Dec
Nostalgia Lane in the heart of the city

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 738 total
includes taxes & fees
25 Dec - 26 Dec
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

The Blue Door steps from Handley Library

2.0 star property
The price is AED 422
AED 707 total
includes taxes & fees
24 Dec - 25 Dec
The Blue Door steps from Handley Library

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

Cameron Grace Brand New 1BR 1BA apt downtown Winchester

2.0 star property
10.0 out of 10, Exceptional, (1)
"Very enjoyable stay right in historical Winchester. We enjoyed walking to a German restaurant for dinner and rested well. "
The price is AED 569
AED 940 total
includes taxes & fees
24 Dec - 25 Dec
Cameron Grace Brand New 1BR 1BA apt downtown Winchester

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

10.0 out of 10, Exceptional, (70)
"This is a beautiful place that had anything you could possibly need to feel at home. We were greeted with homemade pumpkin raisin bread and a bottle of Rose from one of the nearby wineries. The pictures online don’t do the place justice. And the sunrises? Breathtaking! Even had a herd of deer frolicking in the pasture for one sunrise. Our main goals were to relax, unwind and hit as many wineries as we could. The location is perfectly situated between several clusters of wineries. And when we...
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, (12)
"Pam was an amazing host who made us feel at home right from the get-go. This cozy studio above the garage (separate building) on a working farm was quiet and comfortable, made all the moreso by the wonderful people who run it. We enjoyed being there on a farm tour weekend, with the added benefit of a farm stand on site! We look forward to enjoying the honey and produce that we brought back with us… and even moreso, to our next stay. Thanks again!!"
The price is AED 551
AED 992 total
includes taxes & fees
5 Jan - 6 January 2025
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

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
24 Dec - 25 Dec
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

8.0 out of 10, Very Good, (8)
"First we found it strange that you enter into this unit through the bathroom. It is up a laneway behind a house and backs onto a subdivision. The “kitchenette” was not very clean with some leftover packages of food in drawer from previous guests and no microwave. It was a warm day when we arrived and the heat was on full blast and was controlled from another unit. It continued to blast heat for our whole visit. We were to stay for 3 nights and the first night was fine as there were no guests in...
The Outpost Suite 3 - Whimsical Farmhouse Retreat

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

The price is AED 681
AED 1,467 total
includes taxes & fees
5 Jan - 6 January 2025
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

The Royal Loft, Modern 1 Bedroom, Front Royal, VA

The price is AED 459
AED 1,088 total
includes taxes & fees
24 Dec - 25 Dec
The Royal Loft, Modern 1 Bedroom, Front Royal, VA
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

Best Western Dulles Airport Inn

2.5 star property
8.2 out of 10, Very Good, (1146)
"It was clean motel, breakfast was of basic level, ovarall I am satisfied and have no complaints."
The price is AED 278
AED 317 total
includes taxes & fees
24 Dec - 25 Dec
Best Western Dulles Airport Inn

Hyatt Regency Dulles

4.0 star property
8.8 out of 10, Excellent, (1207)
"The entire team at the Hyatt Regency Dulles was welcoming. If I had a question or need, they helped. The lobby area had a private events area, a bistro and bar, and of course the front desk. Also on the Lobby level was the gym and pool area. The gym was pretty decently equipped, the pool was a lap pool, and also in the pool areal was a jacuzzi. All of the areas were spotless. Our room was quite spacious for the price point. It was well laid out and very clean. There was a microwave, small...
The price is AED 364
AED 411 total
includes taxes & fees
5 Jan - 6 January 2025
Hyatt Regency Dulles

Tysons Corner Suites, A Baymont by Wyndham

2.5 star property
7.6 out of 10, Good, (400)
"Niha was excellent. Helped me with all my accomodations. Highly recommend."
The price is AED 294
AED 332 total
includes taxes & fees
29 Dec - 30 Dec
Tysons Corner Suites, A Baymont by Wyndham
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: New Wine Horse Country 10 Acre Lux Retreat amid historic sites. Stunning Views!: Situated in Leesburg, 15.5 mi/24.9 km from the heart of Upperville. Includes free WiFi, private patios, and sofa beds. Cozy 1BR Apt Minutes From Skyline Drive!!: Located 21.8 mi/35.2 km away in Amissville. Free WiFi, private patios, and Smart TVs are included. Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg: It’s situated in Middleburg, 8.8 mi/14.1 km away. 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 Glenwood Park.
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.