The Winchester Inn: A Romantic Getaway in the Heart of Ashland, Oregon

Where Elegance Meets Historic Charm

Nestled in the heart of downtown Ashland, Oregon, The Winchester Inn offers a unique blend of history, luxury, and unparalleled comfort. Established in a building dating back to 1886, the boutique hotel boasts rich Victorian architecture and thoughtfully curated interiors. Once serving as a private home and Southern Oregon’s first hospital, the property has grown into an iconic destination for couples seeking a historic and romantic retreat.

Conveniently located near the renowned Oregon Shakespeare Festival, the inn offers effortless access to both cultural experiences and the vibrant local dining scene in Ashland.

Its meticulously preserved charm, complemented by high-quality, modern amenities, ensures guests an unforgettable stay steeped in both sophistication and warmth.

Accommodations: A Haven of Comfort and Elegance

Guest Rooms and Suites

The Winchester Inn features 21 individually designed rooms and suites, each balancing timeless elegance with contemporary comfort. The accommodations include luxurious bedding with 600-thread-count sheets, flat-screen TVs, private bathrooms stocked with Antica Farmacista toiletries, terry cloth robes, and thoughtful details like fresh flowers and daily turndown service.

For couples seeking extra indulgence, select suites feature amenities like soaking tubs, romantic fireplaces, and private balconies offering scenic views of Ashland.

Cottages

Perfect for couples or small groups, the Winchester Inn also offers charming cottages with private entrances. These accommodations provide a balance of privacy and shared spaces, ideal for those seeking seclusion or a home-like ambiance during their stay.

Fine Dining: Ashland’s Culinary Gems

One of the Winchester Inn’s most notable features is its culinary excellence. The property houses two exceptional restaurants that celebrate the region’s rich culinary heritage.

Alchemy Restaurant and Bar

Known for its award-winning wine list and innovative farm-to-table dishes, Alchemy Restaurant is a must-visit for food enthusiasts. Seasonal, local ingredients are crafted into mouthwatering dishes that showcase creativity and flavor.

Chateaubriand 36 Steakhouse

For those craving a hearty meal, this French-inspired steakhouse offers exquisite cuts of premium meats paired with a warm and elegant atmosphere.

Guests also enjoy an exquisite complimentary gourmet breakfast during their stay, featuring two delicious courses to start the day on a perfect note.

Romantic Ambiance and Exceptional Service

Impeccable Hospitality

The Winchester Inn’s reputation for top-notch service shines through its attentive staff. Whether it is customizing dietary accommodations for breakfast, arranging activities in the vibrant Ashland arts scene, or simply greeting guests with a warm smile, the team is dedicated to providing a memorable experience.

Serene Gardens and Outdoor Spaces

For a quiet moment, guests can retreat to the inn’s beautifully landscaped gardens. Intimate sitting areas surrounded by lush greenery make the gardens an enchanting setting to read, sip wine, or enjoy meaningful conversations with loved ones.

Unbeatable Location

Located steps away from iconic sites like the Oregon Shakespeare Festival, Lithia Park, and the Cabaret Theater, The Winchester Inn is ideal for culture and adventure lovers alike. Ashland’s boutique wineries, galleries, and outdoor activities like hiking trails and rafting are also nearby, making it an excellent base for exploring the beauty of Southern Oregon.

Why Choose The Winchester Inn

For travelers seeking a romantic and luxurious getaway, The Winchester Inn is a quintessential destination. With its rich history, artistic setting, gourmet dining, and thoughtful amenities, the inn guarantees a stay that is as enriching as it is relaxing.