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Compare 10 Guest Houses in Upperville with updated reviews, rates, and availability.

Briar Patch Bed & Breakfast Inn

3.0 star property
7.8 out of 10, Good, (8)
"Charming but rustic farm property with outbuildings. Eclectic, NOT fancy. Very clean, not manicured. This is like staying at a real farm. "
The price is SAR 1,341
SAR 1,529 total
includes taxes & fees
1 Apr - 2 Apr
Briar Patch Bed & Breakfast Inn

Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed

2.0 star property
10.0 out of 10, Exceptional, (11)
"Convenient location in Winchester though the property made it feel like you are in the country. Check in time must be precise as the owner needs to explain a couple things and let you in. This was good as my husband had a couple questions. Toaster oven was missing its tray so it was not easy to use the appliance. Coffee maker and refrigerator work great, bathroom facilities work. The house is in great condition and a neat place to stay."
Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed

Secret Gardens Carriage House

2.0 star property
9.8 out of 10, Exceptional, (19)
"We are so glad we stumbled upon this gem! Looking to find a place to celebrate our anniversary & get away (long overdue), I found Ramana’s garden paradise. It is a quaint 1920’s carriage house with beautiful hardwood floors, a pedestal tub, fully stocked kitchen & large screened in porch for relaxing on those gorgeous evenings! Upon arrival, Ramana greeted us with our keys & a tour of the whole property, including where we would be staying, showing us where we could find organic veggies & herbs...
Secret Gardens Carriage House

Guest House at Mt. Independence

4.0 star property
10.0 out of 10, Exceptional, (3)
"This is the perfect couple's heaven. Beautifully decorated, art in every corner. Comfortable bed, relaxing tub and cozy living room couch. The property is gorgeous and very quiet. 10min away from nice restaurants, bakery and more than a dozen wineries. The national park is just 5min away with great trails and breath taking views. Stephen is very attentive and you can add many services to your stay. My husband and I had the most amazing time and can't wait to be back. "
Guest House at Mt. Independence

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

10.0 out of 10, Exceptional, (3)
"Absolutely loved our stay at Unicorn Hollow. So peaceful. Clean and had everything you needed. Loved the horses and Guiseppe (the donkey) along with the deer and alpacas. Can stroll about the property. Anna and Pino were wonderful to meet. "
The price is SAR 1,032
SAR 1,626 total
includes taxes & fees
1 May - 2 May
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

Guest House at Mt Independence

2.0 star property
10.0 out of 10, Exceptional, (2)
"Had a great time arching the sun rise and set over the blue ridge mountains "
The price is SAR 670
SAR 1,116 total
includes taxes & fees
1 Apr - 2 Apr
Guest House at Mt Independence

Guest House at 1796 Historic Farm in Wine Country

10.0 out of 10, Exceptional, (71)
"I love this property. I came for a return visit, so I knew what to expect. We enjoyed wine by the firepit each night. Thank you! The accommodations are quaint yet top notch. The host family is generous, communicative and accommodating and also respectful of the privacy that we wanted. I book well in advance to make sure I get the date I want to see the Fall colors--there is nowhere better to do this! Thank you!! "
Guest House at 1796 Historic Farm in Wine Country

Chilton House Suites

4.0 star property
9.2 out of 10, Wonderful, (37)
"We were celebrating my wife's birthday and wanted a unique experience. A Bed and Breakfast in Warrenton was our first choice. The furnishings were very nice and enhanced our stay. This is a big plus! On the negative side: (1) Access into the B&B should have been identified as being difficult to navigate due to the number of steps and how steep they were. (2) Our welcome package had the wrong name on it, which is not a big deal, but strange. (3) No layout sketch on the location of our room and...
Chilton House Suites

M&M Suite Near Downtown Leesburg

M&M Suite Near Downtown Leesburg

Weddings at Highholdborne

3.5 star property
Weddings at Highholdborne
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

Cozy Mountain Cabin w/ Steam Shower! Great for Couples.

10.0 out of 10, Exceptional, (59)
"The cabin was beautiful! Brigid has the cabin well stocked. She was very welcoming. Our family with kids and a dog felt very comfortable and even pampered!"
The price is SAR 600
SAR 1,307 total
includes taxes & fees
2 Apr - 3 Apr
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (83)
"Loved it "
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

10.0 out of 10, Exceptional, (37)
"Me and my friends who were visiting from Canada had a wonderful time at this property. The property has been kept in an immaculate condition and the views are just amazing. The host was very responsive and we can’t wait to visit again."
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
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.