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19 Sep - 21 Sep

Apartments in Upperville

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, (17)
"Great two days at the farm. Quiet, clean, and friendly hosts. :) "
The price is AED 551
AED 992 total
includes taxes & fees
27 Jul - 28 Jul
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg
Dining

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

9.4 out of 10, Exceptional, (3)
"The apartment is great. I suspect it would be particularly awesome for a long-term stay. It's a basement apartment, so stairs weren't a surprise. Obviously, if you're not mobile, you won't pick this apartment. However, if you're a little wobbly, the stairs only have one handrail (it's not sketchy, but I rely pretty heavily on my handrails, and this one was not comforting), the bathroom floor is shiny and terrifying, the walk to the unit is bumpy, with lots of tree roots, uphill, and possibly...
Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg
Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg
Exterior detail

Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg

9.6 out of 10, Exceptional, (8)
"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
Historic apartment in Old Town Warrenton, Virginia
Outdoor dining

Historic apartment in Old Town Warrenton, Virginia

9.8 out of 10, Exceptional, (46)
"Great location and comfortable place."
The price is AED 559
AED 859 total
includes taxes & fees
27 Jul - 28 Jul
Historic apartment in Old Town Warrenton, Virginia
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, (88)
"Clean, quiet, and cozy. Thank you for being such great hosts—we really enjoyed our stay!!"
Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues
Cozy 1BR Apt Minutes From Skyline Drive!!
Fridge, microwave, oven, stovetop

Cozy 1BR Apt Minutes From Skyline Drive!!

9.6 out of 10, Exceptional, (31)
"The Cozy Apartment was a nice little stay for our trip to the area including great vineyards, great restaurant (Claire's) in Warrenton, and a great experience in one of our nation's best National Parks - Shenandoah National Park. "
The price is AED 446
AED 845 total
includes taxes & fees
1 Aug - 2 Aug
Cozy 1BR Apt Minutes From Skyline Drive!!
Berryville Bliss: Basement Apartment in welcoming Berryville
Outdoor dining

Berryville Bliss: Basement Apartment in welcoming Berryville

10.0 out of 10, Exceptional, (2)
"Clean, comfortable and close to Historic Rosemont! Pool was incredible!"
The price is AED 744
AED 1,780 total
includes taxes & fees
28 Jul - 29 Jul
Berryville Bliss: Basement Apartment in welcoming Berryville
New - The Skyline Flat
Smart TV, stereo

New - The Skyline Flat

10.0 out of 10, Exceptional, (2)
"Place is awesome and cozy. Perfect setup for a short stay or an extended stay. Owner is easy to reach and responds quickly. "
New - The Skyline Flat
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
Exterior

Romantic African-Inspired Studio on Alpaca Farm – Under the Stars

9.8 out of 10, Exceptional, (9)
"The entire stay was nothing but exceptional. The host was very informative, knowledgeable, and helped make the stay all it can be and then some."
The price is AED 1,286
AED 1,868 total
includes taxes & fees
27 Jul - 28 Jul
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
Cozy English Basement Apt quiet but close to downtown
Exterior

Cozy English Basement Apt quiet but close to downtown

9.6 out of 10, Exceptional, (7)
"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."
Cozy English Basement Apt quiet but close to downtown
Nostalgia Lane in the heart of the city
3 bedrooms, iron/ironing board, WiFi, bed sheets

Nostalgia Lane in the heart of the city

8.8 out of 10, Excellent, (10)
"The apartment has an eclectic layout with great charm. Very clean and perfectly situated to Old Town. "
The price is AED 731
AED 1,286 total
includes taxes & fees
27 Jul - 28 Jul
Nostalgia Lane in the heart of the city
The Blue Door steps from Handley Library
Exterior detail

The Blue Door steps from Handley Library

2.0 star property
7.0 out of 10, Good, (2)
"Perfect. Met all expectations. Small but Great."
The price is AED 294
AED 562 total
includes taxes & fees
4 Aug - 5 Aug
The Blue Door steps from Handley Library
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
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
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 "
Cozy studio close to Skyline Drive, Hiking, and Main Street.
Apple Mountain Retreat
Property grounds

Apple Mountain Retreat

10.0 out of 10, Exceptional, (14)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is AED 496
AED 859 total
includes taxes & fees
25 Jul - 26 Jul
Apple Mountain Retreat
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, (7)
"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 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
Rosamond nice downtown studio apt
Interior

Rosamond nice downtown studio apt

8.0 out of 10, Very Good, (2)
"Small but appropriately priced."
The price is AED 404
AED 707 total
includes taxes & fees
27 Jul - 28 Jul
Rosamond nice downtown studio apt
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Dining

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

9.0 out of 10, Wonderful, (6)
"Lots of stairs to the bedroom and the tub shower was hard to get into for someone with knee problems. The washer dryer was off premises around to the back to the back of the house. wish they had left written instructions about how to get there , had to text her. Location was great!"
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
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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Top Upperville Hotel Reviews

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"Overall very good experience."
willy 1-night trip
Posted 17 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG

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: Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.: Situated in Middleburg, 10.3 mi/16.6 km from the heart of Upperville. Includes free WiFi. 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. 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. 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. Access to onsite laundry facilities is available on site. 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?
Explore the area and family-friendly sights such as Blue Ridge Regional Park, 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.