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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sep - 28 Sep

Cottages in Upperville

Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Bar (on property)

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
Fridge, microwave, oven, stovetop

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
2 bedrooms, WiFi

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 AED 514
AED 858 total
includes taxes & fees
3 Sep - 4 Sep
Wild Hare Cottage
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Dining

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 AED 639
AED 1,979 total
includes taxes & fees
6 Aug - 7 Aug
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Fridge, microwave, oven, stovetop

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!
Private kitchen

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.
Exterior

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
Fridge, microwave, oven, stovetop

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 AED 698
AED 1,630 total
includes taxes & fees
4 Aug - 5 Aug
Royal Heritage Home @ Historic Leesburg
Historical cottage in the town of Paris
Exterior

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!
Pool

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.
Terrace/patio

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!
Fridge, microwave, oven, stovetop

Peaceful Lakefront Cottage with Mountain Views!

9.8 out of 10, Exceptional, (26)
"Really enjoyed stay home was great "
The price is AED 922
AED 2,116 total
includes taxes & fees
20 Aug - 21 Aug
Peaceful Lakefront Cottage with Mountain Views!
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
Terrace/patio

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
Exterior

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
Fridge, microwave, oven, stovetop

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
Exterior

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 AED 1,010
AED 1,446 total
includes taxes & fees
4 Aug - 5 Aug
18th Century Stone Cottage minutes from historic Middleburg
Lake View Retreat - Cottage Near a Peaceful Lake!
Property grounds

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 AED 367
AED 1,321 total
includes taxes & fees
12 Aug - 13 Aug
Lake View Retreat - Cottage Near a Peaceful Lake!
Cottage w/ Hot Tub and 100-Mile Valley Views!
Outdoor spa tub

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 AED 404
AED 1,439 total
includes taxes & fees
13 Aug - 14 Aug
Cottage w/ Hot Tub and 100-Mile Valley Views!
Hike, Sip & Explore: Charming Waterford Cottage!
Living area

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 AED 378
AED 1,110 total
includes taxes & fees
17 Aug - 18 Aug
Hike, Sip & Explore: Charming Waterford Cottage!
Front Royal Retreat ~ 1 Mi to National Park!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Great place! We will be back!"
DEBORAH 1-night trip
Posted 18 hours ago
La Quinta Inn & Suites by Wyndham Winchester

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