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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Upperville apartments

A fenced grassy field with a clear sky and distant hills.

1. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.2 out of 10, Wonderful, (11 reviews)
"Beautiful, peaceful property. We originally lived in the area and were coming back to close out our business in town. The amenities in the home were great and everything was super clean. You definitely get the Northern Virginia rural experience here. Great location and hosts were amazing! Would stay here again!"
United States
Christina C.
The price is CA $190
CA $382 total
includes taxes & fees
Sep 29 - Sep 30
Lunar Loft, with mountain views
A balcony with a table, two wine glasses, and a view of a fenced area with a truck and a building in the background.

2. "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 $305
CA $373 total
includes taxes & fees
Oct 3 - Oct 4
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
A hotel room with a bed, a dining table with chairs, a small table with a vase of flowers, and a storage unit with shelves.

3. 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
9.6 out of 10, Exceptional, (29 reviews)
"The studio has potential but is not worth the price paid. Towels were old, mattress was soft, cobwebs were noticeable. Location is great."
United States
Kathleen
The price is CA $211
CA $382 total
includes taxes & fees
Sep 24 - Sep 25
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
A stone building with a central entrance, a stone staircase, and a landscaped garden.

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

Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
The Plains
10.0 out of 10, Exceptional, (11 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 $492
CA $721 total
includes taxes & fees
Sep 24 - Sep 25
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
A living room with a grey sofa, a wooden staircase, a ceiling fan, and a 'Welcome' sign on the wall.

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

Cozy 1BR Apt Minutes From Skyline Drive!!
Amissville
9.6 out of 10, Exceptional, (46 reviews)
"Everything was clean, cute, and as advertised! The shower pressure"
United States
Kate O.
The price is CA $171
CA $328 total
includes taxes & fees
Sep 24 - Sep 25
Cozy 1BR Apt Minutes From Skyline Drive!!
A white door with a built-in washer and dryer unit.

6. Downtown Apt.1 • 2BR/2BA• Near Park/River• Private

Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Front Royal
The price is CA $236
CA $434 total
includes taxes & fees
Sep 24 - Sep 25
Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
A row of LG washing machines in a showroom.

7. 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, (13 reviews)
"Great location!"
United States
Michelle L.
The price is CA $232
CA $375 total
includes taxes & fees
Sep 30 - Oct 1
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

8. 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 $208
CA $367 total
includes taxes & fees
Sep 24 - Sep 25
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

9. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.8 out of 10, Excellent, (3 reviews)
"Easy space for a 2 person weekend getaway, very close within walking distance to food, shops, breweries, etc"
United States
Jameson D.
The price is CA $155
CA $271 total
includes taxes & fees
Sep 24 - Sep 25
Rosamond nice downtown studio apt
A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a framed picture on the wall.

10. Downtown Apt 3 • 2BR • Near Park & River • Private

Downtown Apt 3 • 2BR • Near Park & River • Private
Front Royal
The price is CA $228
CA $406 total
includes taxes & fees
Oct 14 - Oct 15
Downtown Apt 3 • 2BR • Near Park & River • Private
A patio area with a table and chairs, a small brick building in the background, and a wooden fence.

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

Historic 2-Bedroom in Old Town Warrenton, Virginia
Warrenton
10.0 out of 10, Exceptional, (80 reviews)
"Great stay and utterly charming!"
United States
Jimmy
The price is CA $232
CA $334 total
includes taxes & fees
Oct 14 - Oct 15
Historic 2-Bedroom in Old Town Warrenton, Virginia
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

12. 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
8.4 out of 10, Very good, (6 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 $194
CA $328 total
includes taxes & fees
Sep 24 - Sep 25
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A living room with a sofa, ottoman, lamp, and a mirror.

13. Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is CA $225
CA $426 total
includes taxes & fees
Sep 24 - Sep 25
Morocco Loft 2BR overlooking city walking mall
A living room with a sofa, armchair, coffee table, and a television.

14. 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, (18 reviews)
The price is CA $260
CA $472 total
includes taxes & fees
Sep 24 - Sep 25
Nostalgia Lane in the heart of the city
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

15. 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 $122
CA $370 total
includes taxes & fees
Sep 27 - Sep 28
The Queen of Winchester Three Bedroom with Upper Level Deck
A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

16. 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, (12 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is CA $274
CA $351 total
includes taxes & fees
Sep 24 - Sep 25
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
A dining area with a white table and bench, a hanging light fixture, and a door leading to another room.

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

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Old Town Winchester
9.0 out of 10, Wonderful, (10 reviews)
"Great location…"
United States
John P.
The price is CA $288
CA $526 total
includes taxes & fees
Sep 24 - Sep 25
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
A living room with a sofa, a coffee table, a fireplace, a television, and a dining area in the background.

18. Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.6 out of 10, Exceptional, (8 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is CA $312
CA $558 total
includes taxes & fees
Sep 24 - Sep 25
Scarborough Fair walk to downtown two story apt
A white building with a black door and a set of blue-painted stairs with black railings.

19. The Blue Door steps from Handley Library

The Blue Door steps from Handley Library
Old Town Winchester
5.4 out of 10, (3 reviews)
"Perfect. Met all expectations. Small but Great."
United States
derric3k
The price is CA $161
CA $270 total
includes taxes & fees
Oct 1 - Oct 2
The Blue Door steps from Handley Library
A building with a red door, white trim, and a small balcony with a metal railing.

20. 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 $155
CA $279 total
includes taxes & fees
Oct 4 - Oct 5
The Stock Exchange downtown 3rd floor studio apt
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

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"It was our third time staying here—always such a great place to stay. The staff is the friendliest!"
Joseph 1-night trip
Posted 4 hours ago
Quality Inn Winchester

Find out more about Upperville

Upperville Apartments information

Number of reviews
266
Accommodation
74 Apartments
Lowest Price
CA $270
Highest Price
CA $721

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?
Listed below are some of the favorite apartments in the area to choose from: Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues: Located 14.8 mi/23.8 km away in Leesburg. Free WiFi, private patios, and sofa beds are included. Access to onsite laundry facilities is available on site. Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC: It's located in Winchester, 20.2 mi/32.4 km away. Nostalgia Lane in the heart of the city: Located 20 mi/32.2 km away in Winchester. Amenities include Smart TVs. Access to onsite laundry facilities is available on site. Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.: It's situated in Bluemont, 8.6 mi/13.8 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 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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