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Compare 73 Cottages in Upperville with updated reviews, rates, and availability.

Bear Chase Cottage
Living area

Bear Chase Cottage

10.0 out of 10, Exceptional, (33)
"The cabin was perfect! Clean and cozy. We wish we could have extended our stay! We will definitely come back! "
Bear Chase Cottage
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Terrace/patio

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The price is SAR 938
SAR 1,605 total
includes taxes & fees
12 Jan - 13 Jan
The Cottage at Firefly Cellars, cozy getaway in Loudoun 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, (34)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is SAR 1,032
SAR 1,478 total
includes taxes & fees
9 Feb - 10 Feb
18th Century Stone Cottage minutes from historic Middleburg
Royal Heritage Home @ Historic Leesburg
Living area

Royal Heritage Home @ Historic Leesburg

9.8 out of 10, Exceptional, (24)
"Great location"
The price is SAR 845
SAR 1,826 total
includes taxes & fees
13 Jan - 14 Jan
Royal Heritage Home @ Historic Leesburg
Close to Hiking | Hot Tub | Fire Pit | Pets OK
Our deck is great for relaxing and enjoying the outdoors

Close to Hiking | Hot Tub | Fire Pit | Pets OK

8.0 out of 10, Very Good, (1)
Close to Hiking | Hot Tub | Fire Pit | Pets OK
Spectacular Cottage with Shenandoah River Views
Welcome to the Overlook, perched beautifully above the Shenandoah River

Spectacular Cottage with Shenandoah River Views

10.0 out of 10, Exceptional, (206)
"Overall this was a great place for a getaway with my husband! The cottage is very well done. It's incredibly clean, well stocked, and the furnishings and supplies are quite nice. The view is absolutely gorgeous and very peaceful. The "downsides" were that a bridge is under construction until late 2025 in the area so it takes longer to get to any stores. The last 5 minutes to the property are complete gravel roads and the very last part is a little steep. It's secluded but there is a house next...
Spectacular Cottage with Shenandoah River Views
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Property grounds

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

10.0 out of 10, Exceptional, (16)
"Check in was seamless. The place was perfect for three couples with all the master suites. "
The price is SAR 477
SAR 1,783 total
includes taxes & fees
23 Jan - 24 Jan
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.

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

9.0 out of 10, Wonderful, (6)
"What a stay. Beautiful property, excellent communication with the host, very nice accommodations. "
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Historical cottage in the town of Paris
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (38)
"What a lovely and comfortable cottage! "
Historical cottage in the town of Paris
Cozy Virginia Vacation Rental w/ Seasonal Pool!
Nokesville Vacation Rental | 1BR | 2.5BA | Stairs Required | 800 Sq Ft

Cozy Virginia Vacation Rental w/ Seasonal Pool!

10.0 out of 10, Exceptional, (16)
"This is a wonderful property! Private, secluded area yet not to far from all the amenities that you need! The owners are great and you feel very welcomed at the start of your stay! Highly recommended for a couples retreat!!!"
Cozy Virginia Vacation Rental w/ Seasonal Pool!
Peaceful Lakefront Cottage with Mountain Views!
Enjoy a soak in the hot tub!

Peaceful Lakefront Cottage with Mountain Views!

10.0 out of 10, Exceptional, (22)
"Although short, we had a wonderful stay. Beautiful house with amazing views. Great communication with property host. Cant wait to come back! Thank you for hosting us last minute! "
The price is SAR 481
SAR 1,523 total
includes taxes & fees
15 Jan - 16 Jan
Peaceful Lakefront Cottage with Mountain Views!
Alpacas & The Stars at night. Private Retreat. Fun & Peace
The Cottage showing side entry and seating area. Large BBQ for your convenience

Alpacas & The Stars at night. Private Retreat. Fun & Peace

10.0 out of 10, Exceptional, (44)
"Incredibly comfortable and peaceful. Surrounded by animals of all kinds and great hiking on the property."
Alpacas & The Stars at night. Private Retreat. Fun & Peace
Lake View Retreat - Cottage Near a Peaceful Lake!
This home is just a short walk to Lake Shannondale, and has wintertime views of the lake! Spend your mornings on the front porch, or take a leisurely stroll around the lake.

Lake View Retreat - Cottage Near a Peaceful Lake!

9.4 out of 10, Exceptional, (16)
"Beautiful location to relax and enjoy friends. This house was huge. Plenty of room for the 3 of us...could have been 8, lol. "
The price is SAR 375
SAR 1,332 total
includes taxes & fees
16 Jan - 17 Jan
Lake View Retreat - Cottage Near a Peaceful Lake!
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Fire pit w/custom Adirondack chairs, solar Tiki torches, grapevine arbor

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

9.8 out of 10, Exceptional, (22)
"We enjoyed our stay at the cottage. We were 15-20 minutes away from lots of breweries and outdoor dining places yet felt like we were staying in the country. Enjoyed the hot tub and basketball hoop and the fire pit was ready for us when we arrived. Our little dog was welcomed and enjoyed the yard too. Great communication with the owner. There is some noise from the train and road nearby but it did not bother us."
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Cottage at Gray Fox- Many Attraction- Pet Friendly
Private kitchen

Cottage at Gray Fox- Many Attraction- Pet Friendly

10.0 out of 10, Exceptional, (20)
"Our family of four enjoyed the weekend away"
Cottage at Gray Fox- Many Attraction- Pet Friendly
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, (14)
"The view of this house is amazing! Absolutely beautiful!"
The price is SAR 443
SAR 1,518 total
includes taxes & fees
16 Jan - 17 Jan
Cottage w/ Hot Tub and 100-Mile Valley Views!
Historic Schoolhouse on Winery Row
Quaint, historic village schoolhouse built 1885.

Historic Schoolhouse on Winery Row

10.0 out of 10, Exceptional, (12)
"This VRBO home could not have been any better! It was clean, cozy, comfortable, and well stocked with everything you can possibly need. The owner, Lynn, answered all of our questions and responded to our text messages quickly. She could not have been more helpful. Location is ideal close to wineries and great restaurants. we enjoyed the grill on the back deck as well as the relaxing creek and chairs around the fire pit We enjoyed our stay here so much. We are looking forward to going back...
Historic Schoolhouse on Winery Row
Welcome to the “old town cottage”
Exterior

Welcome to the “old town cottage”

10.0 out of 10, Exceptional, (62)
"I was in town for a 40th birthday party and the locations was great. 15 min walking distance to Old Town. Perfect for two parties with an upstairs bed/full bath and a downstairs bed/full bath. Also, the local egg and chicken sausages were a nice touch! "
Welcome to the “old town cottage”
Charming Home With Yard Near Shenandoah River!
Exterior

Charming Home With Yard Near Shenandoah River!

3.0 star property
10.0 out of 10, Exceptional, (3)
"Cozy house nestled in the mountains of West Virginia. Well-maintained, clean, great yard for pets and/or kids! Lovely grilling and fire pit area. We throughly enjoyed our stay!"
Charming Home With Yard Near Shenandoah River!
Woodsy Retreat with a Hot Tub and Seasonal Views!
Living area

Woodsy Retreat with a Hot Tub and Seasonal Views!

9.8 out of 10, Exceptional, (17)
"We love it! everything was perfect 🤗 we definitely coming back ❤️"
The price is SAR 375
SAR 1,274 total
includes taxes & fees
13 Jan - 14 Jan
Woodsy Retreat with a Hot Tub and Seasonal Views!
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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Other property types in Upperville

Breathtaking views with an indoor private pool, come escape with us
Exterior

Breathtaking views with an indoor private pool, come escape with us

9.8 out of 10, Exceptional, (244)
"We thoroughly enjoyed the cozy lodge vibe and the different spaces it offered our group. The host, Leslie, was always available for any questions we had. She also had the place decorated for Christmas which warmed our hearts!! Thank you Bear Chase for a great weekend. "
Breathtaking views with an indoor private pool, come escape with us
Bear Chase Cottage
Living area

Bear Chase Cottage

10.0 out of 10, Exceptional, (33)
"The cabin was perfect! Clean and cozy. We wish we could have extended our stay! We will definitely come back! "
Bear Chase Cottage
1800s Family Farmhouse with Huge Yard- PRIVATE TRAIL WALK TO WINE!
Outdoor fire place and patio

1800s Family Farmhouse with Huge Yard- PRIVATE TRAIL WALK TO WINE!

10.0 out of 10, Exceptional, (46)
"With grandparents and 2 families with children, not only was the house perfect but the fenced yard was huge and spectacular. We didn’t use the hot tub, but there was plenty of good space for adults, too. We gathered for a family wedding, but the space enabled us to spend a few wonderful relaxing days with family we rarely see. Communication with Leora was prompt and accommodating. 5 stars all around! Thank you!"
1800s Family Farmhouse with Huge Yard- PRIVATE TRAIL WALK TO WINE!
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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