Ashland Dining and Lodging Hotel Logo Winchester Inn in Ashland Oregon
The main hotel building for the Winchester Inn - a boutique hotel and the gardens surrounding it.

Newsletter Signup

Sign up for our newsletter to receive updates and specials


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

Welcome to the Winchester Inn:
The Best Hotel Lodging in Ashland Oregon

Looking for an unforgettable lodging experience at a Hotel in Ashland, Oregon? Look no further – at the Winchester Inn, we redefine luxury and provide a one-of-a-kind hotel stay that combines history, elegance, and exceptional hospitality. Discover why we are considered the best boutique hotel in Ashland, Oregon, and the perfect choice for those seeking a luxury historical lodging experience when visiting Southern Oregon and the Rogue Valley.

Immerse Yourself in Ashland’s Rich History with a Luxury Hotel Stay
Steeped in history, our building has been a part of the Ashland community since it was originally built in 1886 as a private home, and later in 1983, renovated into the boutique hotel that you see today. Nestled in the heart of downtown Ashland, every corner of the Winchester Inn tells a story - from our striking architecture that showcases authentic Victorian charm to our beautifully furnished rooms that offer a window into its past lives as private residence, first Southern Oregon Hospital, and apartment complex. As one of the most historic Ashland, Oregon hotels, we are proud to celebrate the city's vibrant heritage.  You can view more on our history page or visit our historic registry.

Indulge in 5 Star Hotel Service
At the Winchester Inn, we believe that no detail is too small when it comes to making our guests feel treasured. It truly is the small things that make a luxury hotel stay in Ashland so special. Our dedicated staff is here to provide exceptional service at every turn, ensuring your stay in our accommodations exceeds all expectations. Whether you're seeking local restaurant recommendations, need assistance with your travel plans, or simply desire a warm smile, our team is always at your service to make your stay in Ashland a special one.

Luxury Hotel Amenities for your Luxury Hotel Stay
At the Winchester Inn we indulge you in extravagance so that you can enjoy an unforgettable stay at the finest luxury hotel in Ashland, Oregon. With 600 thread count sateen sheets, elegant Antica Farmacista toiletries, and plush cotton towels, not to mention the complimentary gourmet breakfast, we aim to give you the hotel stay that is the epitome of opulence. Whether you're visiting for a business trip, a romantic getaway, or a well-deserved vacation, we guarantee that your stay with us will top all Ashland, Oregon accommodations and surpass your expectations.

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. A photo of the bed in the Eleanore Rose 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

Book Now