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The main hotel building for the Winchester Inn - a boutique hotel and the gardens surrounding it. Located in Downtown Ashland Or.

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Ashland Oregon Downtown Hotel at the Winchester Inn front walkway leading to the main hotel building.

Book your Unforgettable Ashland Hotel Stay Today

When searching for which Ashland Hotel to stay at in downtown Ashland, Oregon choose the finest lodging at the Winchester Inn for an unparalleled experience that seamlessly blends history, elegance, and comfort. Discover why we are the top choice amongst the best and historic hotels in Ashland, Oregon. Secure your luxury accommodations today and create memories that will last a lifetime.

Experience the Winchester Inn – where history meets luxury in the heart of Ashland, Oregon.

Image of the Elizabethan Theater  at the Oregon Shakespeare Festival in Ashland. A picture of a dish from Alchemy Restaurant and Bar located inside the downtown hotel, Winchester Inn. A photo of the bed in the Hargadine suite.

Located just steps away from the world-renowned Oregon Shakespeare Festival, and right around the corner from the Oregon Cabaret Theater, the hotel is perfectly situated for immersing yourself in Ashland's vibrant arts and culture scene.

From Shakespearean plays to thought-provoking contemporary performances, let the Winchester Inn be your gateway to a world theater and the cultural arts.

You will find two of the best restaurants in all of Ashland right here at the Hotel.
Alchemy Restaurant and Bar is onsite for your dining pleasure.  Featuring craft cocktails and an award winning wine list, featuring some of the finest products that Oregon has to offer.
Our sister restaurant, located just across the street, is Chateaubriand 36 our French inspired steakhouse, which features a warm and friendly atmosphere of upscale casual dining.

Our commitment to timeless elegance doesn't come at the expense of modern comfort. With finely appointed accommodations, you'll find blissful relaxation in our luxurious rooms and suites. Each hotel room boasts a unique charm, blending classic design with contemporary hotel amenities to ensure your stay is both memorable and comfortable. From plush beds to indulgent spa-like bathrooms, we know how to pamper our hotel guests.

Front walkway of Boutique Ashland Oregon Hotels Winchester Inn

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Explore the Heart of Downtown Ashland, Or and
Discover the Charm and Comfort of the Winchester Inn
The Best Hotel in Downtown Ashland, Oregon

Explore Ashland Or Hotels Downtown: Stay at the Winchester Inn

If you're looking for Ashland Or hotels downtown, look no further than the Winchester Inn. This premier boutique hotel offers the perfect blend of charm and comfort in the heart of Ashland, Oregon. As one of the finest hotels in Ashland, the Winchester Inn provides an exceptional experience for every guest. Whether you're planning a romantic getaway, a solo retreat, or the best business stay, our hotel in downtown Ashland, Oregon, has the perfect accommodation to suit your needs.

Discover Luxury and Elegance at Ashland's Premier Hotel

At our Ashland OR hotel downtown, we pride ourselves on offering luxurious rooms and suites, each thoughtfully designed with elegant decor and top-of-the-line amenities. Enjoy breathtaking views of the beautiful Ashland landscape while relaxing in the comfort of your room. Our boutique hotel is ideal for couples, families, and solo travelers seeking a peaceful retreat in the heart of Ashland.

Enjoy Unmatched Hospitality and Personalized Service

When you choose the Winchester Inn among other Ashland Or hotels downtown, you can expect exceptional hospitality and personalized service. Our friendly and attentive staff is dedicated to making your stay as comfortable and enjoyable as possible. From the moment you arrive, you'll experience the warmth and welcoming atmosphere that sets us apart from other Ashland hotels downtown.

Experience the Best of Ashland, Oregon

Located conveniently in the heart of downtown Ashland, our hotel is the perfect base for exploring all that this charming city has to offer. Ashland is known for its vibrant arts scene, including the renowned Oregon Shakespeare Festival, as well as its diverse dining options and stunning natural beauty. Staying at one of the best hotels in Ashland OR downtown means you'll have easy access to local attractions, shopping, and outdoor activities.

Book now and discover why we're the top choice for visitors looking for an exceptional stay in Ashland, Oregon.