Search Upperville Cottage Rentals from CA $138

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
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Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Upperville Cottages

Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Relax in a hot tub surrounded by lush greenery under a covered pergola.

Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

9.8 out of 10, Exceptional, (28)
"So much to do in the area, cute little cottage, very clean and comfortable "
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Cozy Stone Cottage in Round Hill, VA
Enjoy a relaxing stay in this charming two-story house with a spacious balcony and a cozy front porch featuring a seating area and stone chimney.

Cozy Stone Cottage in Round Hill, VA

9.6 out of 10, Exceptional, (5)
"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. "
Cozy Stone Cottage in Round Hill, VA
Wild Hare Cottage
Enjoy a peaceful outdoor space with a bench and table, surrounded by a low wall and a view of the well-maintained lawn.

Wild Hare Cottage

10.0 out of 10, Exceptional, (6)
"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!"
The price is CA $193
CA $327 total
includes taxes & fees
Aug 6 - Aug 7
Wild Hare Cottage
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Enjoy a serene river view from this outdoor deck, complete with a grill and comfortable seating.

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

10.0 out of 10, Exceptional, (19)
"Loved this house for relaxing, enjoying nature and reconnecting with friends!"
The price is CA $230
CA $729 total
includes taxes & fees
Aug 6 - Aug 7
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Escape to a serene countryside retreat surrounded by lush greenery and trees.

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

9.8 out of 10, Exceptional, (6)
"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."
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Hunt Country cottage in Upperville!
Step up to the inviting entrance and enjoy the peaceful ambiance of this home's cozy porch area.

Hunt Country cottage in Upperville!

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay and look forward to booking again next year!"
Hunt Country cottage in Upperville!
A Restored Wagon Barn On A 1790's Farm.
Set amidst a lush landscape, this traditional barn features a simple, sturdy construction and a prominent white-framed window.

A Restored Wagon Barn On A 1790's Farm.

10.0 out of 10, Exceptional, (110)
"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."
A Restored Wagon Barn On A 1790's Farm.
Royal Heritage Home @ Historic Leesburg
Enjoy cooking in this well-equipped kitchen with a central island, refrigerator, microwave, and oven.

Royal Heritage Home @ Historic Leesburg

9.6 out of 10, Exceptional, (30)
"The place is great! Clean, comfortable, close to downtown. The host was very responsive and friendly. "
The price is CA $291
CA $647 total
includes taxes & fees
Aug 20 - Aug 21
Royal Heritage Home @ Historic Leesburg
Historical cottage in the town of Paris
Stroll up to the charming entrance, flanked by windows, and enjoy the serene surroundings of this two-story home.

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (45)
"This is a nice home near sky meadow park. A great place to see the stars... Very close to DC. "
Historical cottage in the town of Paris
Cozy Virginia Vacation Rental w/ Seasonal Pool!
Enjoy a serene retreat in this two-story home surrounded by a well-maintained lawn and mature trees.

Cozy Virginia Vacation Rental w/ Seasonal Pool!

10.0 out of 10, Exceptional, (20)
"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."
Cozy Virginia Vacation Rental w/ Seasonal Pool!
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Relax in a serene outdoor setting with two comfortable rocking chairs overlooking a picturesque landscape with lush greenery and a tranquil water feature.

Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.

9.2 out of 10, Wonderful, (10)
"Convenient to where I needed to be. Nice property. Dogs loved the property"
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Peaceful Lakefront Cottage with Mountain Views!
Relax in a serene lakeside setting with a view of lush greenery and trees.

Peaceful Lakefront Cottage with Mountain Views!

9.8 out of 10, Exceptional, (26)
"Really enjoyed stay home was great "
The price is CA $354
CA $805 total
includes taxes & fees
Aug 27 - Aug 28
Peaceful Lakefront Cottage with Mountain Views!
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
Traditional architecture meets serene surroundings in this charming property.

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

8.0 out of 10, Very good, (1)
"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."
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
Weekend getaway short distance from DC/Northern Virginia
Set amidst rolling fields, this traditional two-story building offers a serene rural retreat.

Weekend getaway short distance from DC/Northern Virginia

10.0 out of 10, Exceptional, (86)
"This place was cozy and welcoming, exactly what we were looking for on a weekend away."
Weekend getaway short distance from DC/Northern Virginia
Modern Country Cottage in Wine Country
Stunning home with a charming front porch and detached garage, set amidst a beautifully manicured lawn and lush trees.

Modern Country Cottage in Wine Country

8.8 out of 10, Excellent, (3)
"Description of property was accurate. It worked well for our purpose. Location was.close to Leesburg and easy to get to. Mice"
Modern Country Cottage in Wine Country
18th Century Stone Cottage minutes from historic Middleburg
Cozy cottage surrounded by lush greenery, featuring a large window with white shutters and a stone chimney.

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (46)
"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities. "
The price is CA $379
CA $543 total
includes taxes & fees
Aug 5 - Aug 6
18th Century Stone Cottage minutes from historic Middleburg
Lake View Retreat - Cottage Near a Peaceful Lake!
Traditional home with a charming front porch and beautifully manicured lawn.

Lake View Retreat - Cottage Near a Peaceful Lake!

9.6 out of 10, Exceptional, (18)
"Was really able to relax and enjoy during our brief stay. Would come again."
The price is CA $138
CA $496 total
includes taxes & fees
Aug 20 - Aug 21
Lake View Retreat - Cottage Near a Peaceful Lake!
Cottage w/ Hot Tub and 100-Mile Valley Views!
Relax in a serene hot tub surrounded by lush greenery and breathtaking mountain views.

Cottage w/ Hot Tub and 100-Mile Valley Views!

10.0 out of 10, Exceptional, (18)
"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."
The price is CA $152
CA $540 total
includes taxes & fees
Aug 13 - Aug 14
Cottage w/ Hot Tub and 100-Mile Valley Views!
Hike, Sip & Explore: Charming Waterford Cottage!
Escape to a serene oasis with a pathway leading to a tranquil retreat.

Hike, Sip & Explore: Charming Waterford Cottage!

10.0 out of 10, Exceptional, (2)
"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. ☮️"
The price is CA $142
CA $416 total
includes taxes & fees
Aug 17 - Aug 18
Hike, Sip & Explore: Charming Waterford Cottage!
Front Royal Retreat ~ 1 Mi to National Park!
Houses with unique architectural styles and lush green surroundings.

Front Royal Retreat ~ 1 Mi to National Park!

3.0 star property
Front Royal Retreat ~ 1 Mi to National Park!
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Friendly staff. Good location. Lots of places to eat. Within walking distance. Property was clean. And well maintained. "
Frank 1-night trip
Posted 2 days ago
Comfort Inn & Suites Winchester