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The main building for the boutique bed and breakfast, the Winchester Inn, and the gardens surrounding it.
Ashland Oregon bed and breakfast, the Winchester Inn front walkway leading to the main hotel building.

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Looking for an Ashland Hotel that is the best?
Discover the Charm & Comfort of the Winchester Inn,
a boutique Hotel nestled into downtown Ashland, Oregon

Are you planning a trip to beautiful Ashland, Oregon?

Look no further! Welcome to the Winchester Inn, the premier choice among Ashland hotels. With our unrivaled comfort, exceptional service, and convenient location, we guarantee an unforgettable stay in this enchanting town. Whether you're here for business or pleasure, the Winchester Inn is the perfect hotel in Ashland.

Why choose the Winchester Inn among the multitude of other Ashland hotels? Let us show you the way:

Our rooms and suites are designed with your utmost comfort in mind. Each space is elegantly furnished, featuring plush bedding, luxurious amenities, and modern conveniences. Rest assured, a good night's sleep awaits you at the Winchester Inn.

Our dedicated staff is committed to providing exceptional service, ensuring your every need is met throughout your stay. We pride ourselves on delivering personalized experiences, going above and beyond to make your time in Ashland truly unforgettable.

Situated in the heart of Ashland, the Winchester Inn offers easy access to all the town's attractions. From the world-renowned Oregon Shakespeare Festival to the gorgeous Lithia Park, everything you desire is just a stone's throw away. Explore Ashland's vibrant downtown, filled with charming boutiques, galleries, and delectable dining options – all within walking distance from our hotel.

Indulge your senses with our award-winning on-site restaurant, Alchemy, serving mouthwatering cuisine prepared by our talented team of chefs. Savor a delightful breakfast or enjoy a romantic dinner amidst the cozy ambiance of the Winchester Inn's restaurant and bar. Your taste buds will thank you!

Don't settle for just any Ashland hotel – choose the Winchester Inn for an extraordinary stay. Book your reservation today and experience the epitome of comfort, style, and hospitality in Ashland, Oregon.

Let us be your home away from home.

Book your Unforgettable Ashland Hotel Stay Today

Explore your ideal lodging in Ashland, Oregon by choosing the premier Ashland Hotel – The Winchester. Immerse yourself in an unmatched experience that seamlessly combines history, elegance, and comfort. As the top choice among Ashland hotels, The Winchester ensures a distinctive stay. Secure your luxury accommodations today and craft memories that endure a lifetime.

Discover The Winchester, a boutique hotel where history converges with luxury in the heart of Ashland, Oregon.

Nestled mere steps from the renowned Oregon Shakespeare Festival, our hotel is an ideal haven for those seeking to delve into the rich arts and culture of Ashland.

Whether you crave the timeless allure of Shakespearean plays or the stimulating atmosphere of contemporary performances, let the Winchester Hotel serve as your portal to a realm of artistic discovery.

Enjoy exquisite dining at our Ashland hotel with two top-notch restaurants. Alchemy Restaurant and Bar offers craft cocktails and an award-winning wine list, showcasing the best of Oregon.

Across the street, Chateaubriand 36, our French-inspired steakhouse, provides a warm and friendly atmosphere for upscale casual dining.

We seamlessly blend timeless elegance with modern comfort. Our well-appointed hotel accommodations offer a perfect balance, providing blissful relaxation in luxurious rooms and suites. Each hotel room exudes a unique charm, harmonizing classic design with contemporary amenities to create a memorable and comfortable stay. Pamper yourself with plush beds and indulgent spa-like bathrooms – our commitment to your comfort is unwavering.

BOOK NOW