Name: Winchester Inn
Address: 35 South 2nd Street, Historic Downtown District, Ashland, Oregon, United States of America, Ashland, Jackson County, United States of America
Rating: 9.43

Guest reviews

9.4

Superb

Based on 454 verified reviews

Who stays here?

Business

4%

Couple

67%

Family

12%

Group

14%

Solo

1%

What guests think

AI-generated summary based on recent guest reviews

Across many reviews, Winchester Inn is praised for its walkable downtown Ashland location, comfortable rooms, and standout complimentary breakfast and restaurant, with consistently friendly, professional service enhancing relaxing stays for theatergoers and leisure travelers.

Facilities

Cleanliness

Rooms

Service

Location

Dining

Was this helpful?

10

Damon

4 weeks ago

·

Stayed 2 nights

Fabulous breakfast and a great room. Location is right in town, can't really get a better location for the theatres and downtown restaurants. I stay here often.

10

Stacey

15 Jan 2026

·

Stayed 1 night

The room is fantastic!! Highly recommend!

2

Mei

13 Jan 2026

·

Stayed 1 night

Why it calls itself hotel really puzzles me. Very dated dirty carpet, loud split heating/ac, not to mention nobody checks you in at 11pm with poor instructions. Will NEVER stay here.

8

James

4 Jan 2026

·

Stayed 1 night

Property was beautiful. Room was large, clean and nicely appointed. The only disappointment was not getting to sample the highly rated breakfast as we learned after we made our booking that the kitchen and restaurant were shut down for a yearly deep clean.

10

Willy

23 Dec 2025

·

Stayed 1 night

Beautiful B&B. This will now be our favorite stop in Ashland.

35 South 2nd Street, Historic Downtown District, Ashland, Oregon, United States of America

Location

A stay at Winchester Inn places you in the heart of Ashland, steps from Oregon Cabaret Theatre and 3 minutes by foot from Ashland Library. This inn is 0.2 mi (0.3 km) from Lithia Park and 0.2 mi (0.3 km) from Oregon Shakespeare Festival.

Oregon Cabaret Theatre(0.1 Miles)

Ashland Library(0.2 Miles)

Lithia Park(0.2 Miles)

Oregon Shakespeare Festival(0.2 Miles)

Thomas Theatre(0.2 Miles)

Angus Bowmer Theatre(0.2 Miles)

More location info

Property policies

Check-in instructions

Everything you need to know for a smooth check-in.

Check-in

Check-out

From 16:00 to 21:00

Before 11:00

Good to know

Additional policies and info about this property.

Optional extras

Additional paid services you can request.

FAQs

Yes, free self-parking is available on-site. However, parking is limited.

A complimentary cooked-to-order breakfast is served daily from 8 AM to 9:30 AM.

Check-in is from 4:00 PM to 9:00 PM, and check-out is at 11:00 AM. Early or late check-in/check-out may be available upon request, but additional charges may apply.

The property features step-free entrances and wheelchair-accessible facilities in public areas. Guests are encouraged to contact the property for specific accessibility needs.

The property is located in the heart of Ashland, just steps from the Oregon Cabaret Theatre and a 3-minute walk from Ashland Library. It is 0.2 miles from Lithia Park and the Oregon Shakespeare Festival.

Children are welcome at the property. There is no specified minimum age for children to stay for free.

Winchester Inn

Amenities

Property description

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