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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar

Our top choices for Upperville apartments

Property grounds
Private apartment on a beautiful private farm!

Private apartment on a beautiful private farm!

Private apartment on a beautiful private farm!
Bluemont
8.8 out of 10, Excellent, (6)
"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 AED 496
AED 992 total
includes taxes & fees
8 Jan - 9 Jan
Private apartment on a beautiful private farm!
Outdoor dining
Historic 2-Bedroom in Old Town Warrenton, Virginia

Historic 2-Bedroom in Old Town Warrenton, Virginia

Historic 2-Bedroom in Old Town Warrenton, Virginia
Warrenton
9.8 out of 10, Exceptional, (60)
"Bill’s place was great. Everything was just as described, clean, and comfortable. Bill was very kind and helpful! Awesome stay!"
United States
Joanne R.
The price is AED 545
AED 845 total
includes taxes & fees
10 Jan - 11 Jan
Historic 2-Bedroom in Old Town Warrenton, Virginia
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

Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Warrenton
10.0 out of 10, Exceptional, (4)
"I love staying here! It's cozy and comfortable and in a perfect location. "
United States
Jenny D.
The price is AED 606
AED 976 total
includes taxes & fees
13 Jan - 14 Jan
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
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.

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Middleburg
9.8 out of 10, Exceptional, (22)
"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 AED 551
AED 992 total
includes taxes & fees
8 Jan - 9 Jan
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Property grounds
Apple Mountain Retreat

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (21)
"Great place to stayed "
United States
Mike F.
The price is AED 496
AED 859 total
includes taxes & fees
18 Jan - 19 Jan
Apple Mountain Retreat
Interior
Rosamond nice downtown studio apt

Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very Good, (2)
"Small but appropriately priced."
United States
John M.
The price is AED 404
AED 707 total
includes taxes & fees
4 Feb - 5 Feb
Rosamond nice downtown studio apt
Smart TV
Cozy 1BR Apt Minutes From Skyline Drive!!

Cozy 1BR Apt Minutes From Skyline Drive!!

Cozy 1BR Apt Minutes From Skyline Drive!!
Amissville
9.6 out of 10, Exceptional, (40)
"Nice country setting. Good location for our overall visit. Would stay at this rental again."
United States
PHILLIP N.
The price is AED 446
AED 845 total
includes taxes & fees
8 Jan - 9 Jan
Cozy 1BR Apt Minutes From Skyline Drive!!
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

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
2.0 star property
Winchester Historic District
8.6 out of 10, Excellent, (4)
"Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best."
United States
matthew r.
The price is AED 507
AED 845 total
includes taxes & fees
1 Feb - 2 Feb
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Smart TV
Nostalgia Lane in the heart of the city

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, (14)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is AED 680
AED 1,169 total
includes taxes & fees
8 Jan - 9 Jan
Nostalgia Lane in the heart of the city
Interior
NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
8.0 out of 10, Very Good, (1)
"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 AED 408
AED 1,141 total
includes taxes & fees
4 Feb - 5 Feb
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
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

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Old Town Winchester
10.0 out of 10, Exceptional, (1)
"Beautiful space; helpful host."
United States
Sally C.
The price is AED 808
AED 1,432 total
includes taxes & fees
8 Jan - 9 Jan
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Dining
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

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)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
The price is AED 753
AED 1,303 total
includes taxes & fees
8 Jan - 9 Jan
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Exterior detail
The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
2.0 star property
Winchester Historic District
6.0 out of 10, (1)
The price is AED 404
AED 728 total
includes taxes & fees
29 Jan - 30 Jan
The Stock Exchange downtown 3rd floor studio apt
Exterior
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars

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)
"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 AED 1,286
AED 1,868 total
includes taxes & fees
12 Jan - 13 Jan
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
Smart TV
Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard
Old Town Winchester
7.6 out of 10, Good, (4)
"We loved the character and personality kf both Winchester and"
United States
Jenna N.
The price is AED 536
AED 928 total
includes taxes & fees
1 Feb - 2 Feb
Yellow Submarine trendy basement apt and courtyard
Smart TV, fireplace
Scarborough Fair walk to downtown two story apt

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, (5)
"Charming home! Lovely decor. Was perfect for our stay. Great location, walkable to the historical district. Host was very friendly and communicative. "
United States
Stephanie L.
The price is AED 815
AED 1,440 total
includes taxes & fees
8 Jan - 9 Jan
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
"Clean room, front dest service. "
Andrew 1-night trip
Posted 2 days ago
Quality Inn Winchester

Frequently asked questions

What's it like to stay at an apartment in Upperville?
There are 6 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: Apple Mountain Retreat: Located in Linden, 13.2 mi/21.2 km from the heart of Upperville. Includes free WiFi, private patios, and fireplaces. Access to onsite laundry facilities is available on site. Cozy 1BR Apt Minutes From Skyline Drive!!: Located 21.8 mi/35.2 km away in Amissville. Free WiFi, private patios, and Smart TVs 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. 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. 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.