Name: The George Washington Hotel, A Wyndham Grand Hotel
Price range: $148 total

Salamander Resort And Spa

500 North Pendleton Street Middleburg VA

$693 nightly

$789 total

Sep 27 - Sep 28

Total with taxes and fees

Book a stay at this luxury resort in Middleburg. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Middleburg Community Center and ...

9.2/10 Wonderful! (420 reviews)

"They would not let my wife in the room at check in due to her not being listed as a traveler. Huge inconvenience even though she had her id and I called to tell them to let her in. Pool was open until 6 pm. Wife couldn’t get to the pool cause she wasn’t let in pool area till traveler was set up. ..."

Reviewed on Sep 22, 2026

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

$130 nightly

$148 total

Oct 1 - Oct 2

Total with taxes and fees

Book a stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...

Lansdowne Resort and Spa

44050 Woodridge Pkwy Leesburg VA

$295 nightly

$337 total

Oct 13 - Oct 14

Total with taxes and fees

Book a stay at this golf resort in Leesburg. Enjoy an outdoor pool, a golf course, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...

See all 751 properties in Upperville

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.

Whiskey Hill Cabin a mountain escape in Virginia wine country!

Linden VA

Stay at this cabin in Front Royal. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Deer Lake and George Richard Thompson State Wildlife ...

10/10 Exceptional! (123 reviews)

"Ever clean and welcoming. Would highly recommend this one too anyone."

Reviewed on Aug 16, 2026

Mountain View Bungalow in Front Royal

Front Royal VA

Stay at this vacation home in Front Royal. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shenandoah River and Bing Crosby Stadium are ...

10/10 Exceptional! (41 reviews)

"We are so glad we found this little gem for our 7th wedding anniversary! It was extremely clean and so cozy for the two of us and our dog."

Reviewed on Sep 21, 2026

~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake

Harpers Ferry WV

Book a stay at this family-friendly cabin in Harpers Ferry. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shenandoah Lake Beach and ...

10/10 Exceptional! (104 reviews)

"Great location. Beautiful home-very clean, Easy communication"

Reviewed on Sep 12, 2026

See all properties in Upperville

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.