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
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

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 SAR 507
SAR 1,027 total
includes taxes & fees
27 Aug - 28 Aug
Lunar Loft, with mountain views
Outdoor dining

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 SAR 815
SAR 999 total
includes taxes & fees
30 Aug - 31 Aug
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Desk, iron/ironing board, WiFi (free), bed sheets

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
9.8 out of 10, Exceptional, (28 reviews)
"Easy to get in and out, and the property was clean and tidy!"
United States
Cameron H.
The price is SAR 563
SAR 1,027 total
includes taxes & fees
24 Sep - 25 Sep
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Interior

4. 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.
The price is SAR 451
SAR 1,321 total
includes taxes & fees
7 Sep - 8 Sep
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
TV

5. 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 SAR 556
SAR 983 total
includes taxes & fees
30 Aug - 31 Aug
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Exterior

6. 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 SAR 1,314
SAR 1,934 total
includes taxes & fees
3 Sep - 4 Sep
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
Outdoor dining

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

Historic 2-Bedroom in Old Town Warrenton, Virginia
Warrenton
10.0 out of 10, Exceptional, (76 reviews)
"Great stay and utterly charming!"
United States
Jimmy
The price is SAR 620
SAR 952 total
includes taxes & fees
9 Sep - 10 Sep
Historic 2-Bedroom in Old Town Warrenton, Virginia
Interior

8. 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)
"Great location!"
United States
Michelle L.
The price is SAR 620
SAR 1,010 total
includes taxes & fees
9 Sep - 10 Sep
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Exterior detail

9. 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 SAR 413
SAR 757 total
includes taxes & fees
27 Aug - 28 Aug
The Stock Exchange downtown 3rd floor studio apt
Interior

10. 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 SAR 413
SAR 732 total
includes taxes & fees
6 Sep - 7 Sep
Rosamond nice downtown studio apt
Interior

11. 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)
"Perfect location for walking around Old Town Winchester!"
United States
Clint B.
The price is SAR 488
SAR 825 total
includes taxes & fees
30 Aug - 31 Aug
Pretty Little Apt by the Train II
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 SAR 338
SAR 1,008 total
includes taxes & fees
31 Aug - 1 Sep
The Queen of Winchester Three Bedroom with Upper Level Deck
Smart TV

13. 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)
"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 SAR 695
SAR 1,263 total
includes taxes & fees
27 Aug - 28 Aug
Nostalgia Lane in the heart of the city
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
8.4 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 SAR 518
SAR 864 total
includes taxes & fees
31 Aug - 1 Sep
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Living area

15. 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 SAR 668
SAR 1,229 total
includes taxes & fees
23 Sep - 24 Sep
Morocco Loft 2BR overlooking city walking mall
Private kitchen

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, (8 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is SAR 732
SAR 949 total
includes taxes & fees
6 Sep - 7 Sep
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Private kitchen

17. Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Old Town Winchester
The price is SAR 635
SAR 1,239 total
includes taxes & fees
31 Aug - 1 Sep
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Smart TV

18. Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard
Old Town Winchester
7.6 out of 10, Good, (4 reviews)
"You need to add some kitchen tongs Otherwise everything was fantastic!!!"
United States
Michelle K.
The price is SAR 548
SAR 978 total
includes taxes & fees
15 Sep - 16 Sep
Yellow Submarine trendy basement apt and courtyard
Dining

19. 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 SAR 770
SAR 1,404 total
includes taxes & fees
30 Aug - 31 Aug
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Smart TV, fireplace

20. 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 SAR 834
SAR 1,493 total
includes taxes & fees
27 Aug - 28 Aug
Scarborough Fair walk to downtown two story 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
"We were pleasantly surprised and very pleased with this property. We enjoyed our overnight stay and would definitely stay again. Convenient to I-81, yet surprisingly quiet"
Joyce K 1-night trip
Posted 9 hours ago
Quality Inn Winchester

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: Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC: Located 20.2 mi/32.4 km away in Winchester. Historic 2-Bedroom in Old Town Warrenton, Virginia: Located in Warrenton, 19.7 mi/31.7 km away. Includes free WiFi, private patios, and separate dining areas. 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. Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues: Located in Leesburg, 14.8 mi/23.8 km from Upperville. Includes free WiFi, private patios, and sofa beds. Access to onsite laundry facilities is available on site.
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.