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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Upperville apartments

Property grounds

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
8.8 out of 10, Excellent, (6 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 $185
CA $372 total
includes taxes & fees
Mar 16 - Mar 17
Lunar Loft, with mountain views
Smart TV

Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.0 out of 10, Wonderful, (15 reviews)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is CA $254
CA $460 total
includes taxes & fees
Mar 15 - Mar 16
Nostalgia Lane in the heart of the city
Property grounds

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
10.0 out of 10, Exceptional, (7 reviews)
"Had a fun visit. Property and host we're excellent."
United States
Daniel D.
The price is CA $189
CA $376 total
includes taxes & fees
Mar 17 - Mar 18
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (22 reviews)
"Great place to stayed "
United States
Mike F.
The price is CA $184
CA $316 total
includes taxes & fees
Mar 22 - Mar 23
Apple Mountain Retreat
1 bedroom, desk, iron/ironing board, free WiFi

Cozy Apartment w/ King bed in lovely VA Wine Country; Enough room for up to 6!

Cozy Apartment w/ King bed in lovely VA Wine Country; Enough room for up to 6!
Purcellville
10.0 out of 10, Exceptional, (1 review)
"Had a wonderful stay. The space was very cute and was clean and comfortable. The hosts were helpful and accommodating. We appreciated everything. "
United States
Amanda H.
The price is CA $198
CA $277 total
includes taxes & fees
Mar 18 - Mar 19
Cozy Apartment w/ King bed in lovely VA Wine Country; Enough room for up to 6!
Exterior

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, (9 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 $480
CA $699 total
includes taxes & fees
Mar 15 - Mar 16
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
Living area

Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is CA $244
CA $448 total
includes taxes & fees
Mar 15 - Mar 16
Morocco Loft 2BR overlooking city walking mall
Outdoor dining

Historic 2-Bedroom in Old Town Warrenton, Virginia

Historic 2-Bedroom in Old Town Warrenton, Virginia
Warrenton
9.8 out of 10, Exceptional, (61 reviews)
"The apartment was extremely nice. Everything that was needed for a great stay. I would definitely stay there again."
United States
Tommy N.
The price is CA $204
CA $317 total
includes taxes & fees
Mar 16 - Mar 17
Historic 2-Bedroom in Old Town Warrenton, Virginia
Smart TV

Cozy 1BR Apt Minutes From Skyline Drive!!

Cozy 1BR Apt Minutes From Skyline Drive!!
Amissville
9.8 out of 10, Exceptional, (42 reviews)
"Cozy and clean. We enjoy the peace and quiet and a great and safe area and neighborhood. "
United States
Theresa S.
The price is CA $167
CA $321 total
includes taxes & fees
Mar 15 - Mar 16
Cozy 1BR Apt Minutes From Skyline Drive!!
Desk, iron/ironing board, free WiFi, bed sheets

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, (24 reviews)
"We had an excellent time and our dog loved the farm. The hosts are fantastic people and were very helpful. The room was clean and comfortable. We location is nice just a few minutes drive from downtown Middleburg and in a beautiful area. We will definitely return."
United States
Henri G.
The price is CA $206
CA $374 total
includes taxes & fees
Apr 1 - Apr 2
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Interior

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, (5 reviews)
"I love staying here! It's cozy and comfortable and in a perfect location. "
United States
Jenny D.
The price is CA $225
CA $367 total
includes taxes & fees
Apr 3 - Apr 4
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Interior

Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.8 out of 10, Exceptional, (7 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 $178
CA $297 total
includes taxes & fees
Apr 12 - Apr 13
Pretty Little Apt by the Train II
Interior

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 $151
CA $264 total
includes taxes & fees
Mar 31 - Apr 1
Rosamond nice downtown studio apt
Interior

NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
8.0 out of 10, Very good, (1 review)
"The listing indicated pets were welcome and we were able to bring our 13 year old dog, who loves traveling with my husband and I. There was some initial confusion after we booked the Schoolhouse, saying pets are prohibited. Through contact with the host, it was cleared up pretty quickly. All in all, the place was comfortable and we had what we needed to cook a couple of meals. I loved the area and enjoyed walking our dog on the state-maintained back roads. We would have liked to take advantage...
United States
Kathy S.
The price is CA $123
CA $392 total
includes taxes & fees
Mar 17 - Mar 18
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Exterior detail

The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
6.0 out of 10, (1 review)
The price is CA $151
CA $274 total
includes taxes & fees
Mar 26 - Mar 27
The Stock Exchange downtown 3rd floor studio apt
Interior

Very charming & spacious 2 bedrm

Very charming & spacious 2 bedrm
Winchester
The price is CA $140
CA $257 total
includes taxes & fees
Apr 5 - Apr 6
Very charming & spacious 2 bedrm
Smart TV, fireplace

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, (6 reviews)
"Excellent location, easy walk to most of the Old Town area. Michele is a great host, will definitely stay here again if in the area. "
United States
Larry E.
The price is CA $305
CA $542 total
includes taxes & fees
Mar 15 - Mar 16
Scarborough Fair walk to downtown two story apt
Dining

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, (6 reviews)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
The price is CA $281
CA $513 total
includes taxes & fees
Mar 15 - Mar 16
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Interior

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Old Town Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is CA $302
CA $539 total
includes taxes & fees
Mar 15 - Mar 16
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Smart TV, books

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
8.6 out of 10, Excellent, (4 reviews)
"Large historic house at a great location "
United States
Bryan T.
The price is CA $189
CA $322 total
includes taxes & fees
Mar 31 - Apr 1
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
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 Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG

10/10 Excellent
"Excellent stay and highly recommend if you are headed to the casino! Shuttle service was a great perk. Staff were super friendly and room was exactly as listed. Continental breakfast was delicious and offered more than other hotels! We will be coming back for sure! "
Melody 1-night trip
Posted 5 hours ago
Holiday Inn Express Charles Town by IHG

Find out more about Upperville

Upperville Apartments information

Number of reviews
210
Accommodation
70 Apartments
Lowest Price
CA $257
Highest Price
CA $699

Frequently asked questions

What's it like to stay at an apartment in Upperville?
There are 7 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: Historic 2-Bedroom in Old Town Warrenton, Virginia: Located in Warrenton, 19.7 mi/31.7 km from the heart of Upperville. Includes free WiFi, private patios, and separate dining areas. Access to onsite laundry facilities is available on site. Apple Mountain Retreat: Located 13.2 mi/21.2 km away in Linden. Free WiFi, private patios, and fireplaces are included. Access to onsite laundry facilities is available on site. Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.: It's situated in Middleburg, 10.3 mi/16.6 km away. Includes free WiFi. Cozy Apartment w/ King bed in lovely VA Wine Country; Enough room for up to 6!: 13.5 mi/21.7 km away in Purcellville. Free WiFi, private patios, and fireplaces are included. 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 Blue Ridge Regional Park, 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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