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Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan

Apartments in Upperville

Exterior
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)
"Friendly owner. Came over when I couldn't start the pilot light on the gas wall heater. A few blocks away from some excellent restaurants in the historic district. It's in a remodeled basement with air ducts so head clearance is limited for tall folk."
United States
Dale
The price is AED 367
AED 645 total
includes taxes & fees
10 Dec - 11 Dec
Cozy English Basement Apt quiet but close to downtown
Outdoor dining
Historic apartment in Old Town Warrenton, Virginia

Historic apartment in Old Town Warrenton, Virginia

Warrenton
9.8 out of 10, Exceptional, (57)
"Love the 5 minute walk to restaurants! Also loved staying in an apartment in a historic house. Very nicely furnished and had everything we needed. "
United States
Lynn M.
The price is AED 559
AED 855 total
includes taxes & fees
12 Nov - 13 Nov
Historic apartment in Old Town Warrenton, Virginia
Property grounds
Private apartment on a beautiful private farm!

Private apartment on a beautiful private farm!

Bluemont
8.8 out of 10, Excellent, (6)
"This little farm condo was absolutely perfect for our overnight stay. In fact, I wish we had the opportunity to stay longer. It was lovely to wake up and see chickens and other animals as well as hear the dogs barking. The view of the mountains was also lovely! We will definitely think of staying here again next time we visit our friends!"
United States
Matthew S.
The price is AED 496
AED 992 total
includes taxes & fees
18 Nov - 19 Nov
Private apartment on a beautiful private farm!
Outdoor dining
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, (2)
"Had a fun visit. Property and host we're excellent."
United States
Daniel D.
The price is AED 446
AED 928 total
includes taxes & fees
19 Nov - 20 Nov
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Living area
Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall

2.0 star property
Old Town Winchester
10.0 out of 10, Exceptional, (2)
"Love the location, availability of parking, and the loft was very comfortable and had everything we needed."
United States
Karen S.
The price is AED 654
AED 1,190 total
includes taxes & fees
11 Dec - 12 Dec
Morocco Loft 2BR overlooking city walking mall
Property grounds
Apple Mountain Retreat

Apple Mountain Retreat

Linden
10.0 out of 10, Exceptional, (21)
"My groomsmen and i were able to chsnge, take pictures and watch football. Perfect place, very clean and has everything you could ask for."
United States
Dan K.
The price is AED 496
AED 859 total
includes taxes & fees
14 Nov - 15 Nov
Apple Mountain Retreat
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, (21)
"Beautiful property- great, clean studio- I had a wonderful stay!"
United States
Elizabeth W.
The price is AED 551
AED 1,001 total
includes taxes & fees
9 Dec - 10 Dec
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Fridge, microwave, oven, stovetop
Cozy 1BR Apt Minutes From Skyline Drive!!

Cozy 1BR Apt Minutes From Skyline Drive!!

Amissville
9.6 out of 10, Exceptional, (35)
"The Cozy Apartment was a nice little stay for our trip to the area including great vineyards, great restaurant (Claire's) in Warrenton, and a great experience in one of our nation's best National Parks - Shenandoah National Park. "
United States
Brad & Stacie B.
The price is AED 446
AED 853 total
includes taxes & fees
12 Nov - 13 Nov
Cozy 1BR Apt Minutes From Skyline Drive!!
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, (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
21 Nov - 22 Nov
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Interior
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
13 Nov - 14 Nov
Rosamond nice downtown studio apt
Fridge, microwave, oven, stovetop
Cameron Grace Brand New 1BR 1BA apt downtown Winchester

Cameron Grace Brand New 1BR 1BA apt downtown Winchester

2.0 star property
Winchester
10.0 out of 10, Exceptional, (4)
"Very enjoyable stay right in historical Winchester. We enjoyed walking to a German restaurant for dinner and rested well. "
United States
Brad E.
The price is AED 569
AED 940 total
includes taxes & fees
12 Dec - 13 Dec
Cameron Grace Brand New 1BR 1BA apt downtown Winchester
Exterior detail
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 331
AED 1,033 total
includes taxes & fees
17 Nov - 18 Nov
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Apartment (4 Bedrooms) | Interior
Balcony & Pool Access: Modern Gainesville Home

Balcony & Pool Access: Modern Gainesville Home

3.5 star property
Gainesville
The price is AED 639
AED 1,681 total
includes taxes & fees
7 Dec - 8 Dec
Balcony & Pool Access: Modern Gainesville Home
Iron/ironing board, WiFi, bed sheets
Farm Suite at Valley View Farm

Farm Suite at Valley View Farm

2.0 star property
Delaplane
The price is AED 477
AED 1,047 total
includes taxes & fees
12 Nov - 13 Nov
Farm Suite at Valley View Farm
3 bedrooms, iron/ironing board, WiFi, bed sheets
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, (13)
"The apartment has an eclectic layout with great charm. Very clean and perfectly situated to Old Town. "
United States
Heather P.
The price is AED 680
AED 1,219 total
includes taxes & fees
17 Nov - 18 Nov
Nostalgia Lane in the heart of the city
Fridge, microwave, oven, stovetop
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
12 Nov - 13 Nov
The Stock Exchange downtown 3rd floor studio apt
Fridge, microwave, oven, stovetop
Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard

Old Town Winchester
9.0 out of 10, Wonderful, (2)
"We loved the character and personality kf both Winchester and"
United States
Jenna N.
The price is AED 536
AED 945 total
includes taxes & fees
13 Nov - 14 Nov
Yellow Submarine trendy basement apt and courtyard
Terrace/patio
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, (4)
"We stayed here overnight after our trip to Shenandoah. House had everything we needed for a peaceful night. "
United States
Subra S.
The price is AED 815
AED 1,440 total
includes taxes & fees
12 Nov - 13 Nov
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)
"This is a wonderful historic house in Old Town Winchester. The house is a duplex and is very room. It has the charm of a historic house, but modern amenities. It is very comfortable and check-in was extremely easy (we ended up arriving much later than we had planned, but had no problems accessing the house). The location is absolutely perfect, especially if you want to be in walking distance to all of the cute shops, cafes, and restaurants in the area. Our trip was very fast. We were in town...
United States
Wendy W.
The price is AED 753
AED 1,361 total
includes taxes & fees
9 Dec - 10 Dec
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Microwave, oven, stovetop, dishwasher
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
The price is AED 808
AED 1,432 total
includes taxes & fees
19 Nov - 20 Nov
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
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

Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

10/10 Excellent
"Clean, great design, nice staff"
Steven 1-night trip
Posted 2 days ago
Hampton Inn Winchester-University/Mall Area

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: Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues: Located in Leesburg, 14.8 mi/23.8 km from the heart of Upperville. Includes free WiFi, private patios, and sofa beds. 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. Cozy 1BR Apt Minutes From Skyline Drive!!: Located in Amissville, 21.8 mi/35.2 km away. Includes free WiFi, private patios, and Smart TVs. Access to onsite laundry facilities is available on site. Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.: 10.3 mi/16.6 km away in Middleburg. Amenities include free WiFi. Cameron Grace Charming loft 1-bedroom apt in downtown Winchester: It's situated in Winchester, 19.7 mi/31.8 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 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.