Search Cottages in Upperville

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Compare 66 Cottages in Upperville with updated reviews, rates, and availability.

18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (17)
"Middleburg is a quaint Virginia town with lots of history, and to stay in this 1800 century cottage added to the entire experience. Tim (owner) is absolutely fabulous and so accommodating. Tim spent time with us (by our request) and gave us the history of the cottage and plantation. The cottage is well stocked, comfortable, and exactly as the pictures show. But to sit out on the patio looking out over the landscape was wonderful and so peaceful! Middleburg, itself, is full of wineries, shops and...
The price is AED 992
AED 1,435 total
includes taxes & fees
7 Jul - 8 Jul
18th Century Stone Cottage minutes from historic Middleburg
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
10.0 out of 10, Exceptional, (8)
"This is a charming property that would be a welcome escape anywhere, but the setting is what makes it truly magical. Lush greenery, towering trees and a beautifully landscaped yard provide the perfect backdrop to this Bluemont Escape. The house is stylishly decorated with thoughtful touches throughout. The beds were comfy and the cozy couch with ottoman were perfect for our needs. We would totally recommend this property and look forward to returning."
The price is AED 1,212
AED 1,570 total
includes taxes & fees
17 Jun - 18 Jun
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
Woodsy Retreat with a Hot Tub and Seasonal Views!
10.0 out of 10, Exceptional, (10)
"The cabin was great. Clean, well stocked, and quite. It was just what we needed for a long weekend away from everything. Can't wait to do it again."
Woodsy Retreat with a Hot Tub and Seasonal Views!
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Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
10.0 out of 10, Exceptional, (3)
"The inside of the cottage was very clean. The bathroom towels are like blankets! SO nice! The kitchen is decent (with a little coffee/tea bar and fresh eggs in the refrigerator!!), the living room is spacious and the beds are very comfortable. My only issue with the interior was there was no place to put the luggage in the bedrooms. I had to put my suitcase on the floor and kept having to bend down to get things out of it. It would be nice to have a luggage rack or a small dresser in each room....
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Historical cottage in the town of Paris
10.0 out of 10, Exceptional, (21)
"Cozy, small house that is close to the mountains & hiking. Sky Meadows State Park is very close; the ridge above includes the AT. Civilization vis a vis Middleburg, Marshall, and Purcellville are all within a pleasant, half-hour drive. Eating in the screened-in porch was great!"
The price is AED 621
AED 1,115 total
includes taxes & fees
17 Jun - 18 Jun
Historical cottage in the town of Paris
Welcome to the “old town cottage”
10.0 out of 10, Exceptional, (52)
"We stayed here when in Warrenton to care for a loved one. It was the perfect location between the hospital and town in a lovely quiet neighborhood. House was very clean and had all the amenities we needed. Chase was wonderful to work with and Mike (the owner) was very welcoming. Not only were we given bread, eggs, sausage at the beginning of our stay, we found some beautiful daffodils on our doorstep during our stay. We will definitely be back! Thank you!"
Welcome to the “old town cottage”
Bear Chase Cottage
10.0 out of 10, Exceptional, (26)
"Great place to stay! It was so nice being so close to the brewery, and the fenced in yard was great for our dog!"
Bear Chase Cottage
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
10.0 out of 10, Exceptional, (12)
"Very clean! The outdoor space is amazing and better than photos. Host was super responsive to texting. Wish we would have planned an extra day to just enjoy the house and property more!"
The price is AED 2,351
AED 4,385 total
includes taxes & fees
23 Jun - 24 Jun
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Cozy Virginia Vacation Rental w/ Seasonal Pool!
10.0 out of 10, Exceptional, (5)
"So lovely and relaxing. One small hiccup, which the owners were very quick and professional to fix...thank you!! Wish I could go back and stay during the summer without my nervous dogs! :-}"
Cozy Virginia Vacation Rental w/ Seasonal Pool!
Peaceful Lakefront Cottage with Mountain Views!
10.0 out of 10, Exceptional, (16)
"It was a lovely way to spend our honeymoon I loved it so much will book again with family"
The price is AED 1,003
AED 2,236 total
includes taxes & fees
19 Jun - 20 Jun
Peaceful Lakefront Cottage with Mountain Views!
Alpacas & The Stars at night. Private Retreat. Fun & Peace
10.0 out of 10, Exceptional, (42)
"Very nice place to stay that is generally convenient to several towns and eating places. Hosts were very nice and helpful and we enjoyed getting to know them and their animals. Look forward to returning."
Alpacas & The Stars at night. Private Retreat. Fun & Peace
Lake View Retreat - Cottage Near a Peaceful Lake!
9.6 out of 10, Exceptional, (14)
"This property was a perfect place to stay for our group. While it was a little out of the way, it suited our needs, was clean, and very comfortable. The owners made quick communication with them easy. Definitely recommend!"
Lake View Retreat - Cottage Near a Peaceful Lake!
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
9.8 out of 10, Exceptional, (16)
"Came for my daughters wedding and this place was amazing. Awesome place to relax, firepit to chat around, outside table to enjoy a meal was amazing, comfy beds. Just awesome and amazing stay!!"
The price is AED 1,665
AED 3,075 total
includes taxes & fees
30 Jun - 1 Jul
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Cottage at Gray Fox- Many Attraction- Pet Friendly
10.0 out of 10, Exceptional, (16)
"We needed a b&b for an out of town wedding and this home could not have been more perfect! The hot tub and gaming system were a huge hit and the beds were beyond comfortable. The hosts were also very responsive and flexible! Highly recommend"
Cottage at Gray Fox- Many Attraction- Pet Friendly
Cottage w/ Hot Tub and 100-Mile Valley Views!
10.0 out of 10, Exceptional, (12)
"Great place to stay with our family of 4. The house was clean and had everything we needed. The view is beautiful and the neighborhood is nice and quiet."
The price is AED 1,208
AED 2,525 total
includes taxes & fees
23 Jun - 24 Jun
Cottage w/ Hot Tub and 100-Mile Valley Views!
Historic Schoolhouse on Winery Row
10.0 out of 10, Exceptional, (6)
"House and property are great. Just what we needed and had everything easily accessible. We enjoyed our stay."
Historic Schoolhouse on Winery Row
Charming Home With Yard Near Shenandoah River!
3.5 star property
10.0 out of 10, Exceptional, (1)
Charming Home With Yard Near Shenandoah River!
Historic Charmer - Downtown Leesburg
9.6 out of 10, Exceptional, (13)
"We just completed a lovely stay in Leesburg. The location is great-near bike trails, near great restaurants. The bed was very comfortable which is a big deal for me. We can't wait to return!"
The price is AED 918
AED 1,930 total
includes taxes & fees
18 Jun - 19 Jun
Historic Charmer - Downtown Leesburg
🛶 Huckleberry Hills 🛶 Lake Cottage w/ ✨King Beds✨Hot Tub✨Fast Wifi✨Firepit✨
10.0 out of 10, Exceptional, (20)
"This property was clean and comfortable. It was adequate for our needs. The property manager is very responsive and available if any needs arise. Would definitely stay here again."
The price is AED 1,403
AED 2,529 total
includes taxes & fees
19 Jun - 20 Jun
🛶 Huckleberry Hills 🛶 Lake Cottage w/ ✨King Beds✨Hot Tub✨Fast Wifi✨Firepit✨
Hunt Country cottage in Upperville!
9.6 out of 10, Exceptional, (4)
"absolutely perfect house - close to upperville show grounds and host was awesome for communication"
Hunt Country cottage in Upperville!
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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.

Other property types in Upperville

Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
10.0 out of 10, Exceptional, (30)
"Very clean. Crisp, clean linens. Gorgeous views and surroundings. Extremely responsive. Highly recommend!!"
The price is AED 533
AED 1,214 total
includes taxes & fees
19 Jun - 20 Jun
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (229)
"Loved the view, the pool, brewery and the 3 floors of spaces to sleep worked perfect for our group."
Breathtaking views with an indoor private pool, come escape with us
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
9.6 out of 10, Exceptional, (10)
"We enjoyed the cabin very much. We hiked during the day and was very relaxing coming back to the hot tub and a fire. Thank you for a great stay!!"
The price is AED 624
AED 1,566 total
includes taxes & fees
20 Jun - 21 Jun
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
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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