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Browse Select Upperville Apartments

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

10.0 out of 10, Exceptional, (90)
"Great place and part of Virginia house country (now wine and craft beer country). Accommodations are clean and perfect for my wife and me. "
Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues

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

Cozy 1BR Apt Minutes From Skyline Drive!!

9.6 out of 10, Exceptional, (33)
"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 CA $167
CA $314 total
includes taxes & fees
Aug 23 - Aug 24
Cozy 1BR Apt Minutes From Skyline Drive!!

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

9.8 out of 10, Exceptional, (17)
"Cute farm, nice family. Place as advertised. Close to beautiful country and lots of vineyards."
The price is CA $206
CA $364 total
includes taxes & fees
Aug 20 - Aug 21
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

Berryville Bliss: Basement Apartment in welcoming Berryville

10.0 out of 10, Exceptional, (3)
"Clean, comfortable and close to Historic Rosemont! Pool was incredible!"
The price is CA $249
CA $629 total
includes taxes & fees
Aug 26 - Aug 27
Berryville Bliss: Basement Apartment in welcoming Berryville

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 CA $186
CA $317 total
includes taxes & fees
Aug 25 - Aug 26
Apple Mountain Retreat

Charming 2-bedroom 2nd floor apartment with WiFi, AC in lovely Charles Town

9.6 out of 10, Exceptional, (4)
"Great weekend in Charles Town. The apartment is very walkable to all of the downtown shops and restaurants. Easy off-street parking. A close drive to Harpers Ferry and Antietam. We would absolutely stay there again. "
Charming 2-bedroom 2nd floor apartment with WiFi, AC in lovely Charles Town

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 CA $481
CA $700 total
includes taxes & fees
Aug 24 - Aug 25
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars

Historic apartment in Old Town Warrenton, Virginia

9.8 out of 10, Exceptional, (48)
"The property was top notch! It was as comfortable as any 5 star hotels we have stayed in. Upon arrival we took advantage of the outdoor dining area and had drinks before leaving for dinner. The linens were also soft and fluffy. The rooms were beautifully decorated."
The price is CA $209
CA $316 total
includes taxes & fees
Aug 23 - Aug 24
Historic apartment in Old Town Warrenton, Virginia

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

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

8.8 out of 10, Excellent, (10)
"Great location in the heart of Winchester. Walking distance to everything. "
The price is CA $254
CA $447 total
includes taxes & fees
Aug 20 - Aug 21
Nostalgia Lane in the heart of the city

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 CA $158
CA $265 total
includes taxes & fees
Sep 14 - Sep 15
The Blue Door steps from Handley Library

National at Loudoun

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

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

Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street

10.0 out of 10, Exceptional, (3)
"Clean, cute, hot water, cool inside. I would stay again!!!"
The price is CA $182
CA $304 total
includes taxes & fees
Aug 23 - Aug 24
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street

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.

Private apartment on a beautiful private farm!

10.0 out of 10, Exceptional, (4)
"Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. "
The price is CA $202
CA $393 total
includes taxes & fees
Aug 17 - Aug 18
Private apartment on a beautiful private farm!

Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg

9.4 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

Charming Loft In Winchester Va, Furnished and all Inclusive

7.4 out of 10, Good, (3)
"Nice property, everything works well. It's a perfect space for two people. If you're looking to explore the city and just come back to relax, it's a good option for you."
Charming Loft In Winchester Va, Furnished and all Inclusive
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