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Our top choices for Upperville apartments

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

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Markham
9.6 out of 10, Exceptional, (5 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 $264
CA $396 total
includes taxes & fees
Nov 9 - Nov 10
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

2. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.4 out of 10, Exceptional, (13 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 $191
CA $367 total
includes taxes & fees
Nov 9 - Nov 10
Lunar Loft, with mountain views

3. 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, (15 reviews)
"Nice owner, great place"
United States
Leslie C.
The price is CA $196
CA $458 total
includes taxes & fees
Nov 10 - Nov 11
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

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
9.6 out of 10, Exceptional, (29 reviews)
"Easy to get in and out, and the property was clean and tidy!"
United States
Cameron H.
The price is CA $212
CA $367 total
includes taxes & fees
Nov 8 - Nov 9
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

5. 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, (12 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 $491
CA $686 total
includes taxes & fees
Dec 7 - Dec 8
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars

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

Downtown Apt 3 • 2BR • Near Park & River • Private
Front Royal
10.0 out of 10, Exceptional, (1 review)
"This property is absolutely perfect: great location for walking through the historic part of town, close to food & fun, very well appointed (right down to quality toilet paper!) & perfectly clean. Yuliya responded very quickly from the moment I made the reservation to checkout. We would stay again for sure! Thank you, Yuliya & Mark!"
United States
kim B.
The price is CA $229
CA $389 total
includes taxes & fees
Nov 12 - Nov 13
Downtown Apt 3 • 2BR • Near Park & River • Private

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 $233
CA $361 total
includes taxes & fees
Nov 15 - Nov 16
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street

8. 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 $106
CA $334 total
includes taxes & fees
Nov 30 - Dec 1
The Queen of Winchester Three Bedroom with Upper Level Deck

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 $259 total
includes taxes & fees
Nov 12 - Nov 13
Rosamond nice downtown studio apt

10. 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
8.8 out of 10, Excellent, (5 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 $209
CA $354 total
includes taxes & fees
Nov 19 - Nov 20
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

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

Cozy 1BR Apt Minutes From Skyline Drive!!
Amissville
9.6 out of 10, Exceptional, (48 reviews)
"Everything was clean, cute, and as advertised! The shower pressure"
United States
Kate O.
The price is CA $177
CA $324 total
includes taxes & fees
Nov 8 - Nov 9
Cozy 1BR Apt Minutes From Skyline Drive!!

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

Historic 2-Bedroom in Old Town Warrenton, Virginia
Warrenton
10.0 out of 10, Exceptional, (85 reviews)
"Great stay and utterly charming!"
United States
Jimmy
The price is CA $267
CA $391 total
includes taxes & fees
Nov 8 - Nov 9
Historic 2-Bedroom in Old Town Warrenton, Virginia

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 $250
CA $437 total
includes taxes & fees
Nov 17 - Nov 18
Morocco Loft 2BR overlooking city walking mall

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 CA $195
CA $319 total
includes taxes & fees
Nov 15 - Nov 16
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

15. Executive Suites

Executive Suites
3.0 star property
Winchester
The price is CA $357
CA $404 total
includes taxes & fees
Nov 8 - Nov 9
Executive Suites

16. 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 $267 total
includes taxes & fees
Nov 12 - Nov 13
The Stock Exchange downtown 3rd floor studio apt

17. Downtown Apt 2 • 2BR • Near Park & River • Private

Downtown Apt 2 • 2BR • Near Park & River • Private
Front Royal
The price is CA $229
CA $416 total
includes taxes & fees
Nov 10 - Nov 11
Downtown Apt 2 • 2BR • Near Park & River • Private

18. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
8.8 out of 10, Excellent, (21 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 $449 total
includes taxes & fees
Nov 17 - Nov 18
Nostalgia Lane in the heart of the city

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

Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Front Royal
10.0 out of 10, Exceptional, (1 review)
"Perfect for a quick stay over when going to shenedoah natl park. Location is awesome. Very clean and spacious! Highly recommend!"
United States
Maureen N.
The price is CA $237
CA $418 total
includes taxes & fees
Nov 12 - Nov 13
Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
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.

Learn more about Upperville

Hunt country elegance shines at the historic Upperville Horse Show, America's oldest running exhibition where equestrians compete each June. Wander through the quaint village to discover stone buildings, antique shops, and Sky Meadows State Park's hiking trails nearby in Paris.

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

Top reviews in Upperville

Frequently Asked Questions

What's it like to stay at an apartment in Upperville?

There are 9 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. Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.: 8.6 mi/13.8 km away in Bluemont. Nostalgia Lane in the heart of the city: Located in Winchester, 20 mi/32.2 km from Upperville. Includes Smart TVs. 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 Great Country Farms, 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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