Search Upperville Cottages

Upfront pricing

Our total price for your stay includes taxes and fees

Treat yourself

Save 10% or more on over 100,000 hotels worldwide with Member Prices

Learn about One Key

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Cottages in Upperville

"So much to do in the area, cute little cottage, very clean and comfortable "

"We had an excellent stay at cottage! It was perfect for a short weekend away with girlfriends. It was quaint and historic but didn't lack modern day comforts. Highly recommend for anyone looking for a few days away, with easy access to all Round Hill & Purcellville has to offer. "

"We had just a quick overnight stay, the cottage is cozy, clean, and charming. Communication was easy and clear, we'd love to stay again!"

$208 nightly

Aug 6 - Aug 7

Total includes taxes and fees

"Loved this house for relaxing, enjoying nature and reconnecting with friends!"

$458 nightly

Aug 6 - Aug 7

Total includes taxes and fees

"This was a good place to stay for two guys day hiking in the AT. It is clean, quiet, comfortable, and in a very good location. It had everything we needed."

"We had a wonderful stay and look forward to booking again next year!"

"Great stay! Close to Appalachian Trail hiking (Bears Den and Ravens Rock), close to some great breweries and wineries, close to some wonderful restaurants...very peaceful setting with open floor plan on main level. Really enjoyed the time spent here."

"The place is great! Clean, comfortable, close to downtown. The host was very responsive and friendly. "

$410 nightly

Aug 20 - Aug 21

Total includes taxes and fees

"This is a nice home near sky meadow park. A great place to see the stars... Very close to DC. "

"Our stay was fabulous! The cottage is clean, comfortable, and in a peaceful location. The host checked in on us and left a nice welcome gift. I would definitely recommend staying here if in the area."

"Convenient to where I needed to be. Nice property. Dogs loved the property"

"Really enjoyed stay home was great "

$525 nightly

Aug 27 - Aug 28

Total includes taxes and fees

"The cottage was charming, very clean, & comfortable. Just wished the garden wasn’t connected to the cafe right next door. That said, the location was perfect as you could walk downtown which has cute shops & great restaurants."

"This place was cozy and welcoming, exactly what we were looking for on a weekend away."

"Description of property was accurate. It worked well for our purpose. Location was.close to Leesburg and easy to get to. Mice"

"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities. "

$367 nightly

Aug 6 - Aug 7

Total includes taxes and fees

"Was really able to relax and enjoy during our brief stay. Would come again."

$327 nightly

Aug 20 - Aug 21

Total includes taxes and fees

"Great tucked away location for a friends weekend. Some cute towns with good restaurants not too far. Beautiful views from the hot tub. House was very cute and beds were comfortable. Showers worked well and plenty of towels. Working fireplace was also nice."

$345 nightly

Aug 13 - Aug 14

Total includes taxes and fees

"Susan was delightful. She had thought of everything to make our stay comfortable. A wonderful backyard for our precious dog.The cottage was cozy and comfortable and easily accessible.Certainly recommend it to anyone who would love to stay in an historical town along with an environmentally focused community. Wineries and a few breweries as well. We would certainly rent this cottage again. ☮️"

$265 nightly

Aug 17 - Aug 18

Total includes taxes and fees