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
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 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)
"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 SAR 507
SAR 1,027 total
includes taxes & fees
15 Sep - 16 Sep
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
7 Sep - 8 Sep
"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
9.6 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 SAR 563
SAR 1,027 total
includes taxes & fees
6 Sep - 7 Sep
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Exterior

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

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 great"
United States
Lori Anne
The price is SAR 456
SAR 888 total
includes taxes & fees
3 Sep - 4 Sep
Cozy 1BR Apt Minutes From Skyline Drive!!
Interior

6. 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
16 Sep - 17 Sep
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
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, (78 reviews)
"Great stay and utterly charming!"
United States
Jimmy
The price is SAR 620
SAR 952 total
includes taxes & fees
8 Sep - 9 Sep
Historic 2-Bedroom in Old Town Warrenton, Virginia
TV

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

9. 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 830 total
includes taxes & fees
3 Sep - 4 Sep
Pretty Little Apt by the Train II
Fridge, microwave, oven, stovetop

10. 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 Queen of Winchester Three Bedroom with Upper Level Deck
Exterior detail

11. 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 Stock Exchange downtown 3rd floor studio apt
Smart TV, books

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 SAR 518
SAR 889 total
includes taxes & fees
3 Sep - 4 Sep
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Interior

13. 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.
Rosamond nice downtown studio apt
Smart TV

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)
"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 1,255 total
includes taxes & fees
21 Sep - 22 Sep
Nostalgia Lane in the heart of the city
Exterior detail

15. 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 SAR 432
SAR 727 total
includes taxes & fees
30 Sep - 1 Oct
The Blue Door steps from Handley Library
Living area

16. 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.
Morocco Loft 2BR overlooking city walking mall
Private kitchen

17. 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 944 total
includes taxes & fees
15 Sep - 16 Sep
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Smart TV, fireplace

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 SAR 834
SAR 1,493 total
includes taxes & fees
10 Sep - 11 Sep
Scarborough Fair walk to downtown two story apt
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 1,412 total
includes taxes & fees
20 Sep - 21 Sep
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Private kitchen

20. 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
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Excellent"
Marian 1-night trip
Posted 4 hours ago
La Quinta Inn & Suites by Wyndham 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: Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!: Located 20.1 mi/32.3 km away in Winchester. Nostalgia Lane in the heart of the city: Located in Winchester, 20 mi/32.2 km away. Includes Smart TVs. 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. Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC: It's situated in Winchester, 20.2 mi/32.4 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.