Search Guest Houses in Upperville from CA $339

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Check prices for these dates

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Aug 15 - Aug 17
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Upperville Guest Houses

Briar Patch Bed & Breakfast Inn
Seasonal outdoor pool

Briar Patch Bed & Breakfast Inn

3.0 star property
7.8 out of 10, Good, (9)
"A lovely setting...breakfast was fantastic...cook was charming & everything was tasty & homemade. "
The price is CA $432
CA $493 total
includes taxes & fees
Aug 5 - Aug 6
Briar Patch Bed & Breakfast Inn
Guest House at Mt. Independence
Flat-screen TV

Guest House at Mt. Independence

4.0 star property
10.0 out of 10, Exceptional, (3)
"Beautiful Guest House well appointed on beautiful acreage. Would encourage everyone to visit. Host was very helpful and accommodating. You will enjoy the stay ! "
Guest House at Mt. Independence
Guest House at Mt Independence
Interior

Guest House at Mt Independence

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great property, conveniently located to attractions. Host was extremely responsive and friendly. Home and surrounding property was immaculate. We will be staying here again when back in the area. "
The price is CA $339
CA $670 total
includes taxes & fees
Aug 10 - Aug 11
Guest House at Mt Independence
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (4)
"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 CA $341
CA $555 total
includes taxes & fees
Aug 6 - Aug 7
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
Riverfront Oasis with Mountain Views, close to town
Exterior

Riverfront Oasis with Mountain Views, close to town

10.0 out of 10, Exceptional, (19)
"We had a fantastic time. Everything was lovely. Thank you!"
Riverfront Oasis with Mountain Views, close to town
Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed
Outdoor dining

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

2.0 star property
10.0 out of 10, Exceptional, (11)
"Going to visit Luray caverns and the Shenandoah mountains while out at this beautiful tiny home was amazing for the weekend."
Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed
Secret Gardens Carriage House
Property grounds

Secret Gardens Carriage House

2.0 star property
9.8 out of 10, Exceptional, (19)
"Winchester was such a lovely town with so many things to do and see. We enjoyed coming home to the cottage each night with its screened-in patio and relaxing view of flowers and shade trees. The cottage was cozy and clean with plenty of linens and staples. I would stay here again, the location was excellent."
Secret Gardens Carriage House
Weddings at Highholdborne
Front of property - evening/night

Weddings at Highholdborne

3.5 star property
Weddings at Highholdborne
M&M Suite Near Downtown Leesburg
Property grounds

M&M Suite Near Downtown Leesburg

M&M Suite Near Downtown Leesburg
Chilton House Suites
Terrace/patio

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
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Friendly staff. Good location. Lots of places to eat. Within walking distance. Property was clean. And well maintained. "
Frank 1-night trip
Posted 2 days ago
Comfort Inn & Suites Winchester