Property style
This 5-star hotel in ASHLAND, OR offers accommodations suited for a variety of travel needs.
Hotel details & availability
Winchester Inn
ASHLAND, OR
Current availability and rates for Winchester Inn
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Hotel overview
About Winchester Inn
A quick planning snapshot for Winchester Inn in ASHLAND, OR.
Winchester Inn is a hotel located in ASHLAND, OR. Expect upscale amenities, quality service and a premium experience.
Winchester Inn is set in Ashland, only 300 metres from Oregon Shakespeare Festival. Guests can enjoy the on-site bar and restaurant, featuring an outdoor patio. Free parking is also included. Each room at this hotel is air conditioned and features a flat-screen TV. Bedding includes 600 thread count sheets, along with a down feather bed, pillows, and comforter. Certain rooms have a seating area for your convenience. A balcony or patio are featured in certain rooms. Every room includes a private bathroom, complete with Egyptian cotton towels. For your comfort, you will find bathrobes and free imported toiletries. Guests will be provided a 2-course gourmet breakfast each at no additional cost. A coffee bar is also available to guests at the Winchester Inn. You will find concierge service at the property. The hotel is located 2.5 km from Southern Oregon University. Rogue Valley Airport is 24 km away.
Best for
Winchester Inn in ASHLAND, OR can be suitable for couples, families, groups and business travelers, depending on the room type and services you choose.
Booking tip
When checking availability at Winchester Inn, pay attention to the room type, board plan (such as breakfast or all inclusive) and the cancellation policy to find the option that best matches your trip. The hotel is located in ASHLAND, OR, which offers local dining, shopping and entertainment options for visitors.
Destination base
Stay in ASHLAND, OR with access to local attractions, dining and transportation options.
Compare before booking
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Location
ASHLAND, OR
Category
5 stars
Check-in
2026-11-08
Check-out
2026-11-15
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Good to know before booking
Room features, services, facilities, fees and included amenities can vary by selected room type,
rate, destination rules and property policy. Review the available option details before checkout.
Room details vary
Room features, services and facilities can change by selected room type and rate.
Local fees may apply
Taxes, resort fees or destination fees may apply depending on local rules and property policy.
Some extras cost more
Parking, spa access, premium drinks or transfers may require an extra charge.
Frequently asked questions about Winchester Inn
Quick answers about availability, location and trip fit before you continue to room options.
How can I check availability for Winchester Inn?
Use the availability button on this page to search your dates, room options and current rates.
Where is Winchester Inn located?
Winchester Inn is located in ASHLAND, OR. The listed address is 35 SOUTH 2ND STREET.
Is Winchester Inn suitable for families or couples?
Many hotels in ASHLAND, OR welcome different types of travelers. Exact services for families, couples or business travelers depend on the property and the selected room type.