Winchester Inn

This boutique collection of Victorian dwellings is just up the street from the world renowned Oregon Shakespeare Festival.

Located on a quiet hillside with English tiered gardens graced with a picturesque gazebo, this vintage collection of Victorian dwellings are just up the street from the world- renowned Oregon Shakespeare Festival, the Oregon Cabaret Theatre, shopping, and exciting art galleries.

However, it is not its proximity to Ashland's theaters that distinguishes this inn. Innkeepers Michael and Laurie Gibbs have created a destination in itself. The rooms are a wonderful assemblage of Victorian charm and contemporary amenities.

The critically acclaimed Alchemy Restaurant and Bar boasts an award winning menu featuring craft cocktails and boutique wines. Premiere among their special events is the Dickens' Christmas Feast.

Amenities include: Air-conditioning, Breakfast included, Business friendly, Children welcome, Conference facilities, Corporate rates, Fireplaces, Internet access, Spa services, Wedding facilities, Whirlpool tubs

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Contact Information

For reservations call 1.800.972.4991

Phone: 1.541.488.1113

Innkeeper: Michael, Laurie and Drew Gibbs

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Location & Directions

Just one half block above Main Street downtown Ashland on South Second Street.

35 S. Second Street, Ashland, OR, 97520, United States

Specials & Packages


Wine and Cheese - Wine and cheese in room. Please call us with wine preferences. - $50One Dozen Roses - $50Enjoy a half dozen chocolate truffles made by our skilled chefs. - $30Bouquet of Flowers - $50...

Wine Lover's Package

When you check into your room, you will find a bottle of sparkling wine as well as a special selection from the Inn's sommelier especially for your pleasure. Please let them know your preferences on wine.