Search Apartment Rentals in Upperville

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Upperville apartments

Cozy 1BR Apt Minutes From Skyline Drive!!

Cozy 1BR Apt Minutes From Skyline Drive!!
Amissville
9.8 out of 10, Exceptional, (43 reviews)
"Love that my pet was welcome. Very quiet location and felt like home. "
United States
Theresa S.
The price is CA $165
CA $318 total
includes taxes & fees
May 4 - May 5
Cozy 1BR Apt Minutes From Skyline Drive!!

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (23 reviews)
"Great place to stayed "
United States
Mike F.
The price is CA $183
CA $315 total
includes taxes & fees
May 4 - May 5
Apple Mountain Retreat

Historic 2-Bedroom in Old Town Warrenton, Virginia

Historic 2-Bedroom in Old Town Warrenton, Virginia
Warrenton
9.8 out of 10, Exceptional, (64 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 $224
CA $343 total
includes taxes & fees
May 4 - May 5
Historic 2-Bedroom in Old Town Warrenton, Virginia

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
8.8 out of 10, Excellent, (8 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 $183
CA $370 total
includes taxes & fees
May 4 - May 5
Lunar Loft, with mountain views

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)
"Lovely clean room."
United States
Rory O.
The price is CA $204
CA $372 total
includes taxes & fees
May 4 - May 5
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

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 $177
CA $297 total
includes taxes & fees
May 4 - May 5
Pretty Little Apt by the Train II

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, (16 reviews)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is CA $251
CA $453 total
includes taxes & fees
May 4 - May 5
Nostalgia Lane in the heart of the city

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, (10 reviews)
"The location was perfect for my needs, the apartment was super cute - a charming older home with modern upgrades and a designer feel. The host was very communicative and welcoming, so I had all the information I needed and knew just what to expect. I hope I get a chance to stay there again! "
United States
Ren
The price is CA $166
CA $366 total
includes taxes & fees
May 5 - May 6
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

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, (6 reviews)
The price is CA $223
CA $312 total
includes taxes & fees
May 5 - May 6
Cozy Apartment w/ King bed in lovely VA Wine Country; Enough room for up to 6!

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 $242
CA $440 total
includes taxes & fees
May 4 - May 5
Morocco Loft 2BR overlooking city walking mall

Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
9.6 out of 10, Exceptional, (7 reviews)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
United States
Anonymous traveller
The price is CA $136
CA $239 total
includes taxes & fees
May 24 - May 25
Cozy English Basement Apt quiet but close to downtown

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 $476
CA $697 total
includes taxes & fees
May 4 - May 5
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars

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, (8 reviews)
"I love staying here! It's cozy and comfortable and in a perfect location. "
United States
Jenny D.
The price is CA $224
CA $364 total
includes taxes & fees
May 10 - May 11
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street

The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.8 out of 10, Good, (7 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 $128
CA $284 total
includes taxes & fees
May 11 - May 12
The Queen of Winchester Three Bedroom with Upper Level Deck

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 $149
CA $271 total
includes taxes & fees
May 4 - May 5
The Stock Exchange downtown 3rd floor studio apt

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 $122
CA $391 total
includes taxes & fees
May 4 - May 5
NEW! Historic Schoolhouse HotTub+FirePit+Wineries

"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, (1 review)
"Kay and Joe are wonderful guests. They went above and beyond to made us feel so welcomed. The Love Nest is the most cozy and wonderful place we stayed in. Their property is gorgeous and very peaceful. Everything we needed to unwind from a hard week. We will be coming back soon!"
United States
Mariana F.
The price is CA $295
CA $351 total
includes taxes & fees
May 4 - May 5
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

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 $302
CA $534 total
includes taxes & fees
May 4 - May 5
Scarborough Fair walk to downtown two story apt

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
8.8 out of 10, Excellent, (5 reviews)
"Large historic house at a great location "
United States
Bryan T.
The price is CA $188
CA $319 total
includes taxes & fees
May 4 - May 5
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

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
9.2 out of 10, Wonderful, (7 reviews)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
The price is CA $279
CA $505 total
includes taxes & fees
May 4 - May 5
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Upperville Hotel Reviews

Find out more about Upperville

Upperville Apartments information

Number of reviews
247
Accommodation
60 Apartments
Lowest Price
CA $239
Highest Price
CA $697

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: Cozy Apartment w/ King bed in lovely VA Wine Country; Enough room for up to 6!: Situated in Purcellville, 13.5 mi/21.7 km from the heart of Upperville. Includes free WiFi, private patios, and fireplaces. 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. Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.: It's located in Bluemont, 8.6 mi/13.8 km away. Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street: Located 19.6 mi/31.5 km away in Warrenton. Amenities include Smart TVs. Access to onsite laundry facilities is available on site. Historic 2-Bedroom in Old Town Warrenton, Virginia: Located in Warrenton, 19.7 mi/31.7 km from Upperville. Includes free WiFi, private patios, and separate dining areas. 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 RdV Vineyards.
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.

Explore a world of travel with Expedia