The Best Winery Hotels in Winchester, VA from SAR 304 in 2025

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Top Winchester Winery Hotels

1 bedroom, pillowtop beds, desk, laptop workspace

"The hotel was clean, staff was great and breakfast was great."

SAR 474 total

includes taxes & fees

3 Sep - 4 Sep

"Great staff. Good breakfast."

SAR 473 total

includes taxes & fees

7 Sep - 8 Sep

"This home is lovely and the host has thought of everything. We will definitely stay here again. "

SAR 1,531 total

includes taxes & fees

30 Sep - 1 Oct

"We enjoyed our stay. We liked the room and the fact it was close to town which made going places easy. "

SAR 652 total

includes taxes & fees

10 Sep - 11 Sep

"Beautiful house. Renovations are not quite complete yet, and the electronic locks needed extra communication with the owner to use, but still a great stay. Perfect location and this place will be gorgeous after renovations are complete."

SAR 1,179 total

includes taxes & fees

7 Sep - 8 Sep

"You will not be disappointed in this gem. Perfect for day trips to the National Forest or the nation’s capital. Or just enjoy the beautiful scenery. Hosts bend over backwards to accommodate you. "

SAR 1,066 total

includes taxes & fees

2 Sep - 3 Sep

"Clean comfortable fully stocked within walking distance to everything Leesburg has to offer -a GREAT place to stay ... beds were so comfy and so was the sofa definitely would stay again ... totally loved it!! "

SAR 1,016 total

includes taxes & fees

1 Sep - 2 Sep