Best Wine Country Hotel
Experience the Charm of Wine Country at the Winchester Inn in Ashland, Oregon

Discover Our Unique Wine Country Experience

Located in the picturesque Rogue Valley, Ashland is a hidden gem in Oregon’s wine country, known for its award-winning wineries and beautiful vineyards. As one of the top wine country hotels, the Winchester Inn provides easy access to the area's finest wine-tasting experiences and offers a perfect retreat for wine enthusiasts. Often described with the same reverence of Napa and Sonoma when you could still meet the wine maker and have a chance to see who is really making the fine Oregon wines you're tasting.

Why Choose The Winchester Inn?

Award-Winning Boutique Hotel: Named #6 Best Wine Country Hotel by USA Today, our inn is celebrated for its exceptional hospitality and unique charm.

Ideal Location: Situated in downtown Ashland, The Winchester Inn offers convenient access to local wineries, vineyards, and the renowned Oregon Shakespeare Festival. Visit the Ashland Chamber of Commerce for all the guides you might need.

Luxurious Accommodations: Enjoy elegantly designed rooms and suites featuring modern amenities, comfortable furnishings, and stunning views of the surrounding landscape.

Gourmet Breakfast Included: Delight in a delicious complimentary two course gourmet breakfast served each morning, made with fresh, locally sourced ingredients, in house baked pastries, and luxurious entrees.

Explore the Best of Ashland and Beyond

The Winchester Inn is more than just a place to stay; it’s your gateway to the best experiences Ashland and the surrounding wine country have to offer.  Featuring two restaurants, the flagship and Wine Spectator Award wining Alchemy Restaurant, located on the main floor of the hotel, and the newer French inspired steakhouse across the street, Chateaubriand 36, both feature Oregon wines at the forefront of their wine programs. Together they feature more than 800 different wines featuring deep verticals of Oregon wines along with some of the best wines from around the world.

Wine Tours and Tastings

Rogue Valley Wineries: Explore the vibrant wine scene in Rogue Valley, known for its diverse selection of wines, including Tempranillo, Syrah, Malbec, and Viognier.  With over 150 wineries in Southern Oregon you are never at a loss for finding the perfect tasting, especially with Rogue Valley Vintners to help guide you to the prefect route.

Local Wine Tours: Join guided wine tours and tastings that showcase the best of Oregon’s wine country, from boutique vineyards to well renowned wineries.

Outdoor Adventures

Hiking and Biking: Discover the natural beauty of Southern Oregon with scenic hikes through Lithia Park, Grizzley Peak, Mt. Ashland, and mountain bike trails that offer breathtaking views of the gorgeous Rogue Valley and the surrounding Cascade mountains and beautiful vineyards and wineries.

Outdoor Activities: Enjoy white water rafting, fishing, and more in the nearby rivers and lakes, perfect for nature lovers and adventure seekers.

Cultural Attractions

Oregon Shakespeare Festival: Immerse yourself in the world-famous Oregon Shakespeare Festival, featuring a diverse array of plays and performances that go beyond just Shakespeare. 2025 will mark the Oregon Shakespeare Festival's 90th anniversary and will not be something to miss.  It also makes the perfect evening activity after a day of amazing wine tasting.

Arts and Culture: Explore Ashland’s vibrant arts scene, with galleries, theaters, and live music events that showcase the local talent and creativity.

Indulge in Exceptional Hospitality

At The Winchester Inn, we pride ourselves on offering personalized service and a welcoming atmosphere. Our dedicated staff is here to ensure your stay is as comfortable and enjoyable as possible, catering to your every need and creating a memorable experience.

Amenities You’ll Love

Concierge Service: Our friendly concierge is available to assist with recommendations and bookings for local attractions, wine tours, and dining.

On-Site Gift Shop: Browse our charming gift shop for unique souvenirs and locally crafted items.

Meeting and Banquet Facilities: Perfect for special events, weddings, and corporate gatherings, our versatile spaces cater to your needs.

Book Your Stay at The Winchester Inn

Don't miss the opportunity to experience one of the best wine country hotels in the U.S. The Winchester Inn is your ideal choice for a luxurious and memorable wine country getaway in Ashland, Oregon. Book your stay today and indulge in the charm, elegance, and exceptional hospitality that only The Winchester Inn can offer.