Book Guest Houses in Upperville, VA
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Top Guest Houses in Upperville
Briar Patch Bed & Breakfast Inn
23130 Briar Patch Ln Middleburg VA
$275 nightly
The price is $314 total per night
$314 total
Dec 26 - Dec 27
Total with taxes and fees
This guesthouse features a seasonal outdoor pool and a hot tub. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. Barbecue grills are provided for your convenience.
Pool
Hot Tub
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains VA
$369 nightly
The price is $395 total per night
$395 total
Dec 22 - Dec 23
Total with taxes and fees
This guesthouse features a garden, laundry facilities, and barbecue grills.
Free WiFi
Air conditioning
Guest House at Mt Independence
Delaplane VA
This guesthouse features a garden, laundry facilities, and barbecue grills.
Pet friendly
Free WiFi
Riverfront Oasis with Mountain Views, close to town
Middletown VA
This guesthouse featured laundry facilities and barbecue grills.
Free WiFi
Air conditioning
Guest House at Mt. Independence
2254 Winchester Rd Delaplane VA
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and an off-leash area. A garden, a picnic area, and express check-out are also on offer.
Spa
Pet friendly
Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed
Winchester VA
This guesthouse includes a garden and laundry facilities.
Air conditioning
Parking available
Secret Gardens Carriage House
Winchester VA
This guesthouse includes a garden and laundry facilities.
Air conditioning
Parking available
Weddings at Highholdborne
19729 Ridgeside Rd Bluemont VA
This guesthouse features a restaurant, a gym, and a bar/lounge. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. A 24-hour business center, a coffee shop, and a garden are also on offer.
Pool
Breakfast included
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.
Top hotels in Upperville
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
$555 nightly
The price is $632 total per night from Jan 5 to Jan 6
$632 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
9.2/10 Wonderful! (372 reviews)
Upperville Guest Houses essential information
Accommodation | 9 Guest Houses |
|---|---|
Lowest Price | $81 |
Highest Price | $632 |
Popular accommodation | Briar Patch Bed & Breakfast Inn, Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment, Guest House at Mt Independence, Riverfront Oasis with Mountain Views, close to town , Guest House at Mt. Independence, Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed, Secret Gardens Carriage House, Weddings at Highholdborne, Chilton House Suites |
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