The 3 Best Bed & Breakfasts Around Winchester

Bed and breakfasts continue to attract travelers looking for a more personal and immersive alternative to traditional hotel lodging. Throughout Winchester, Frederick County, and the Northern Shenandoah Valley, historic inns and boutique retreat properties blend overnight accommodations with regional dining, event hosting, and heritage tourism experiences. The Star Awards highlight destinations that combine hospitality, preservation, and distinctive local character while helping introduce visitors to the area’s history, food culture, and scenic countryside.

Wayside Inn

Wayside Inn traces its origins back to 1797, making it one of the oldest continuously operating inns in the United States. Originally established as Wilkinson’s Tavern, the property preserves its historic identity through antique furnishings, traditional architecture, and connections to the region’s stagecoach and Civil War history. Under the culinary leadership of Bill and Amanda Whitson, the inn also houses Clem’s Kitchen, which combines updated Southern cuisine with the property’s longstanding hospitality and event traditions.

Inn At Vaucluse Spring

The Inn at Vaucluse Spring offers boutique accommodations spread across several restored historic buildings, including private cabins and estate-style lodging spaces designed around relaxation and wellness-focused travel. Following a major renovation, the property entered a new chapter under Chef Proprietor Jan Van Haute, whose vision combines upscale lodging with sustainability and farm-to-table dining experiences through the inn’s on-site restaurants. The business also maintains close partnerships with local farmers, wineries, and artisans to create a hospitality experience centered on regional food and agriculture.

L’Auberge Provencale

L’Auberge Provençale operates as a French-inspired country inn and culinary destination centered around a historic farmhouse dating back to 1753. Founded by Chef Alain Borel and his wife Celeste, the property offers boutique lodging, executive retreats, private events, and nationally recognized dining supported by an extensive wine program directed by sommelier Christian Borel. The inn’s culinary philosophy emphasizes Provençal techniques combined with seasonal ingredients sourced from local farms, on-site gardens, and orchard production throughout the region.

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