A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Upperville apartments

Property grounds

1. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.0 out of 10, Wonderful, (10 reviews)
"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. "
United States
Haley M.
The price is CA $189
CA $380 total
includes taxes & fees
Aug 11 - Aug 12
Lunar Loft, with mountain views
Property grounds

2. Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Bluemont
9.8 out of 10, Exceptional, (12 reviews)
"Nice owner, great place"
United States
Leslie C.
The price is CA $174
CA $382 total
includes taxes & fees
Aug 17 - Aug 18
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Outdoor dining

3. "The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Markham
10.0 out of 10, Exceptional, (4 reviews)
"Such a lovely stay. The property was peaceful and relaxing, and the night sky was absolutely beautiful. We loved our time here and would happily return. Great communication (and snacks) too :)"
United States
Melissa B.
The price is CA $304
CA $370 total
includes taxes & fees
Aug 9 - Aug 10
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Desk, iron/ironing board, WiFi (free), bed sheets

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

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Middleburg
9.8 out of 10, Exceptional, (27 reviews)
"Easy to get in and out, and the property was clean and tidy!"
United States
Cameron H.
The price is CA $210
CA $383 total
includes taxes & fees
Aug 16 - Aug 17
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Property grounds

5. Apple Mountain Retreat

Apple Mountain Retreat
Linden
9.8 out of 10, Exceptional, (27 reviews)
"Great place to stayed "
United States
Mike F.
The price is CA $189
CA $321 total
includes taxes & fees
Aug 8 - Aug 9
Apple Mountain Retreat
Interior

6. NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
9.4 out of 10, Exceptional, (3 reviews)
"We were staying at the schoolhouse to go hiking and ride bikes. They house has been tastefully decorated. I enjoyed the quite community and the listening to the tree frogs at night. Front Royal has a few things you can enjoy such as the movie theatre, bakery and state park. I would highly recommend this propery."
United States
Suzanne J.
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Smart TV

7. Cozy 1BR Apt Minutes From Skyline Drive!!

Cozy 1BR Apt Minutes From Skyline Drive!!
Amissville
9.6 out of 10, Exceptional, (45 reviews)
"Everything was great"
United States
Lori Anne
The price is CA $170
CA $327 total
includes taxes & fees
Aug 7 - Aug 8
Cozy 1BR Apt Minutes From Skyline Drive!!
Exterior

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

Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
The Plains
9.8 out of 10, Exceptional, (10 reviews)
"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."
United States
Joe D.
The price is CA $490
CA $719 total
includes taxes & fees
Aug 9 - Aug 10
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
Outdoor dining

9. Historic 2-Bedroom in Old Town Warrenton, Virginia

Historic 2-Bedroom in Old Town Warrenton, Virginia
Warrenton
10.0 out of 10, Exceptional, (74 reviews)
"Great stay and utterly charming!"
United States
Jimmy
The price is CA $231
CA $352 total
includes taxes & fees
Aug 9 - Aug 10
Historic 2-Bedroom in Old Town Warrenton, Virginia
Terrace/patio

10. Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
9.6 out of 10, Exceptional, (8 reviews)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
United States
Anonymous traveller
The price is CA $140
CA $246 total
includes taxes & fees
Aug 9 - Aug 10
Cozy English Basement Apt quiet but close to downtown
Interior

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

Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Warrenton
10.0 out of 10, Exceptional, (12 reviews)
"I love staying here! It's cozy and comfortable and in a perfect location. "
United States
Jenny D.
The price is CA $231
CA $377 total
includes taxes & fees
Aug 16 - Aug 17
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Fridge, microwave, oven, stovetop

12. The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.6 out of 10, Good, (8 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
The price is CA $171
CA $431 total
includes taxes & fees
Aug 9 - Aug 10
The Queen of Winchester Three Bedroom with Upper Level Deck
TV

13. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Winchester Historic District
10.0 out of 10, Exceptional, (2 reviews)
"The unit is very nice, exactly as described, The bed are comfortable and everything was fine. The location is excellent very near to historical sights and downtown shopping district."
United States
Timothy B.
The price is CA $207
CA $368 total
includes taxes & fees
Aug 13 - Aug 14
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Smart TV, books

14. Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester Historic District
8.8 out of 10, Excellent, (5 reviews)
"Loved being so close to the old town; was able to walk to a lot of places. Great to have an assigned parking spot in a lot behind the building. Enjoyed staying here a lot!"
United States
Leslie L.
The price is CA $193
CA $327 total
includes taxes & fees
Aug 31 - Sep 1
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Smart TV, fireplace

15. Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.8 out of 10, Exceptional, (7 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is CA $311
CA $557 total
includes taxes & fees
Aug 10 - Aug 11
Scarborough Fair walk to downtown two story apt
Interior

16. Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.6 out of 10, Exceptional, (9 reviews)
"This was yhe perfect place for us to stay in Old Winchester. A short walk to just about everything. The apartment was clean and comfortable. We had no issues with checking in and communication was great with the property owner. We would definitely rent from them again."
United States
Stephanie L.
The price is CA $182
CA $303 total
includes taxes & fees
Aug 30 - Aug 31
Pretty Little Apt by the Train II
Interior

17. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very good, (2 reviews)
"Small but appropriately priced."
United States
John M.
The price is CA $154
CA $270 total
includes taxes & fees
Aug 25 - Aug 26
Rosamond nice downtown studio apt
Exterior detail

18. The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
7.0 out of 10, Good, (2 reviews)
"Everything went smoothly. Easy stay. Clean. Small efficiency with futon for bed."
United States
Greg A.
The price is CA $154
CA $279 total
includes taxes & fees
Aug 16 - Aug 17
The Stock Exchange downtown 3rd floor studio apt
Private kitchen

19. Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Old Town Winchester
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is CA $273
CA $348 total
includes taxes & fees
Aug 31 - Sep 1
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Smart TV

20. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.2 out of 10, Wonderful, (17 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
The price is CA $259
CA $468 total
includes taxes & fees
Aug 16 - Aug 17
Nostalgia Lane in the heart of the city
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

8/10 Good
"Had to go back to desk 2 times after checking in while my wife stood outside our room with luggage in the hall because the keys didn't work. Very frustrating! Also, only 7 channels worked on the TV, was told this was Comcast fault."
Jason 1-night trip
Posted 9 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG

Find out more about Upperville

Upperville Apartments information

Number of reviews
292
Accommodation
80 Apartments
Lowest Price
CA $246
Highest Price
CA $719

Frequently asked questions

What's it like to stay at an apartment in Upperville?
There are 8 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: Apple Mountain Retreat: Located in Linden, 13.2 mi/21.2 km from the heart of Upperville. Includes free WiFi, private patios, and fireplaces. Access to onsite laundry facilities is available on site. Historic 2-Bedroom 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. Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues: Located in Leesburg, 14.8 mi/23.8 km away. Includes free WiFi, private patios, and sofa beds. Access to onsite laundry facilities is available on site. Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.: 8.6 mi/13.8 km away in Bluemont. Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.: It's located in Middleburg, 10.3 mi/16.6 km from Upperville. Includes free WiFi.
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 Dinosaur Land, 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.

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