Tel:  +1 541-488-1113     ‍‍‍ [email protected]

Logo for the RedTail InnLogo for Winchester Inn located in Ashland, Oregon


Main House

Garden Room

Sylvan Room

Queen Ann Room

Sunset Room

Patio Room

Robert Gordon Suite

Peter Benjamin Room

Marjorie Roy Room

Courtyard Suite

Belvedere Suite

Eastlake Room

Enders Room

Fordyce Suite

Hargadine Suite

Catharine M. Room

Andrew G. Room

Barbara Howard Suite

Eleanor Rose Suite

Brighton Suite

Silverdale Suite

Duet Suite

Heritage House

Larkspur Cottage

Carriage House

Enders Cottage

Louisa Suite

Orliena Suite

The RedTail Inn

Red McCall Suite

Guest rooms

Our Guest Rooms are spread throughout the property. Rooms feature queen and king beds with their own private baths.  All guest rooms have flat screen TVs, honor bars, Antica Farmacista toiletries, robes, and gourmet breakfast for two.

Some guest rooms do feature a fireplace or private balcony. Please inquire upon booking.

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Looking for Hotels in Ashland Oregon?

We find that at the Winchester Inn you have all of Ashland at your fingertips.

Every Winchester Inn guest room is appointed with fresh flowers and afternoon pastry treats, plush terry cloth robes, flat screen televisions, and Antica Farmacista toiletries in the ensuite bathroom. Evening turndown service insures everything is perfect for you arrival back to the room. Additional services available for our guests include morning through evening valet service, same day laundry service and room service at breakfast. Rooms are serviced twice daily by housekeeping.

Complimentary high speed wireless internet access is available throughout the property. Enjoy the gardens with many small sitting areas to accommodate a quiet moment with a book or glass of wine. Explore all our unique lodging options – many with romantic fireplaces and beautiful views of the hills across Ashland.

As of 2017, the Winchester Inn will have a total of 21 rooms and suites, each that invokes a color palette that pulls from classic and contemporary styling. Inquire as to which room is the perfect fit for your travels to Ashland.


Our Suites all share the same distinction, luxury. Each suite showcase itself in unique ways, offering soaking tubs, jacuzzi baths or magnificent showers with beautifully intricate marble tile.  All suites feature luxurious beds and that extra space that you might need to really relax, as well as flat screen TVs, honor bars, Antica Farmacista toiletries, robes, and gourmet breakfast for two.

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Our cottages are the perfect accommodation for couple or families with the ability to share the same building but maintain privacy, each features distinct spaces that set them apart from the rest of the property with extra spaces for larger groups to gather and relax.  All cottages come with private entrances and feature flat screen TVs, honor bars, Antica Farmacista toiletries, robes, and gourmet breakfast for all guests.

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