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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 1,342
SAR 1,529 total
includes taxes & fees
16 Apr - 17 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 1,611 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 717
SAR 1,177 total
includes taxes & fees
6 May - 7 May
Guest House at Mt Independence

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

Weddings at Highholdborne

3.5 star property
Weddings at Highholdborne

M&M Suite Near Downtown Leesburg

M&M Suite Near Downtown Leesburg
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

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (84)
"This beautiful cabin has everything you need for a wonderful stay. My husband and I stayed here for our 44th anniversary while visiting local wineries. It was a perfect location."
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

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

10.0 out of 10, Exceptional, (61)
"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 638
SAR 1,354 total
includes taxes & fees
21 Apr - 22 Apr
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (38)
"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities. "
The price is SAR 1,032
SAR 1,478 total
includes taxes & fees
21 Apr - 22 Apr
18th Century Stone Cottage minutes from historic Middleburg
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.