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Recent guest reviews

We loved this quaint beautiful cozy inn. The room was beautiful, the grounds were so pretty. Will definitely return. Highly recommend this quaint inn.

The breakfasts were wonderful! Several choices each morning which is different from most B&Bs. It was quiet, although we were there midweek. Staff is very nice and friendly. I did get a deal, so not sure I would pay the regular price to stay, but it was well worth it for us this time.

Gorgeous and comfortable with numerous high quality touches. Very courteous and helpful staff, a first class operation in every way.

Grat hotel and right downtown, only a couple of blocks from the Oregon Shakespeare Festival heaters. Unbelievable breakfast and super friendly staff!

S. 2nd St. Ashland OR

Hotel highlights

  • Free cooked-to-order breakfast
  • Free WiFi in rooms and public areas
  • Free parking
  • Onsite dining

Located in Historic Downtown District, Winchester Inn is adjacent to Oregon Cabaret Theatre and within a 5-minute walk of Ashland Library. This 21-room, 3.5-star inn welcomes guests with free breakfast, free in-room WiFi, and free self parking.


Dining

Free cooked-to-order breakfast is included with your stay and awaits you each morning from 8 AM to 9:30 AM. You can enjoy a drink at the bar/lounge or visit the onsite restaurant for a bite to eat.


Rooms

All of Winchester Inn's 21 individually decorated rooms provide coffee makers, fans, and phones. Flat-screen TVs come with cable channels, and guests can stay connected with free WiFi. Bathrooms offer hair dryers and designer toiletries, and pillowtop beds with Egyptian cotton sheets and down comforters ensure a restful night. Ironing boards are also available.


Property features

Guests of Winchester Inn enjoy free WiFi in public areas, a meeting room, and free newspapers. If you plan to drive, free parking is available. Front-desk staff can assist with tours or tickets, dry cleaning/laundry, and luggage storage. Additional amenities include a terrace, a garden, and a gift shop.

Room options

Double Room, 1 Bedroom (Sylvan)

1 Queen Bed and 1 Double Sofa Bed | Sleeps 2

Suite, 1 King Bed (Barbara Howard)

1 King Bed | Sleeps 2

Suite, 1 Queen Bed with Sofa bed (Courtyard)

1 Queen Bed and 1 Double Sofa Bed | Sleeps 2

Suite, 1 King Bed (Fordyce)

1 King Bed | Sleeps 2

Guest reviews for Winchester Inn

Everyone (2) Couples (2)
5
Partner Couples

We loved this quaint beautiful cozy inn. The room was beautiful, the grounds were so pretty. Will definitely return. Highly recommend this quaint inn.

By on Jul 24, 2021

5
Partner Couples

The breakfasts were wonderful! Several choices each morning which is different from most B&Bs. It was quiet, although we were there midweek. Staff is very nice and friendly. I did get a deal, so not sure I would pay the regular price to stay, but it was well worth it for us this time.

By , from Corvallis on May 11, 2019

Review comment responded on May 16, 2019

Thank you so much for joining us. It is wonderful to hear that you enjoyed your stay!

5
Everyone

Gorgeous and comfortable with numerous high quality touches. Very courteous and helpful staff, a first class operation in every way.

By , from Oregon on Nov 13, 2018

Review comment responded on Nov 15, 2018

Bill, Thank you so much for taking the time to write about your time at the Winchester Inn. We are delighted to hear that you enjoyed your stay and loved the small touches around the property. We hope to see you next time you're in Ashland.

5

great location upscale decor

Everyone

Grat hotel and right downtown, only a couple of blocks from the Oregon Shakespeare Festival heaters. Unbelievable breakfast and super friendly staff!

By , from Chico, CA on Aug 17, 2018

Review comment responded on Aug 23, 2018

Thank you for taking the time to review the Winchester and your stay. We are delighted to hear about your experience and would like to apologize about our internet, it is an ongoing issue we are working to fix. We do pride ourselves in our customer service and are happy to hear it met your expectations. We do hope to see you next time you are visiting Ashland

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