Free
Children allowed

Facilities

Offsite parking discounted rates available
Non-smoking rooms
Air conditioning
Restaurant
Family rooms
Luggage storage
Fax/photocopying
Facilities for disabled guests
Non-smoking throughout
Concierge service
See all facilities

Review Highlights

Pros:
Charming location
Amazing breakfast
Cons:
Old building issues
Staff availability after hours

Categories

Cleanliness
8.49
Some reviews indicated cold breakfasts and issues with old carpeting.
Service
9.96
Generally high praise for helpful and friendly staff, although some service issues mentioned.
Location
10
Repeatedly described as excellent with a charming downtown position.
Room Quality
9.45
Rooms are spacious and comfortable, though some noted age and creakiness.
Amenities
9.48
Amenities like breakfast and bar are highlighted positively, but there were some complaints about the breakfast temperature.
Value for Money
9.44
Value considered high due to included breakfast and overall experience.
Food and Beverage
9.99
Breakfast is frequently praised as outstanding, with mentions of delicious food.
Overall Experience
10
Overall positive sentiment; many patrons express intent to return and high satisfaction.
* This sentiment is summarized by AI based on user reviews.
Updated at: 2026-01-28 06:54

Property Description

Luxurious Accommodations
Winchester Inn, located just 300 metres from the Oregon Shakespeare Festival, offers elegantly appointed rooms with 600 thread count sheets, down feather bedding, and private balconies or patios. The rooms are equipped with modern amenities including flat-screen TVs and air conditioning, ensuring a comfortable stay for all guests.

Gourmet Dining Experience
Guests at Winchester Inn can indulge in a 2-course gourmet breakfast included in their stay, prepared with fresh ingredients. The on-site bar and restaurant with an outdoor patio offer a perfect setting to unwind and enjoy delicious meals. Additionally, a coffee bar is available for guests to grab a quick pick-me-up throughout the day.

Concierge Service and Convenience
The hotel provides concierge service to assist guests with any inquiries or bookings, ensuring a seamless and enjoyable stay. With free parking on-site and proximity to Southern Oregon University and Rogue Valley Airport, Winchester Inn offers convenience and accessibility for all travelers.

Book your stay at Winchester Inn now for a luxurious and memorable experience!

Important information:

Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.
Please inform of your expected arrival time in advance. You can use the Special Requests box when booking, or contact the property directly using the contact details in your confirmation.

Check-in and check-out hours:
Check-out: 11:00 AM
Airport code: MFR

Property Policies

  • Parking

    Free private parking is possible on site (reservation is not needed).

  • Internet

    WiFi is available in all areas and is free of charge.

  • Pets

    Pets are not allowed.

  • Children and extra bed policy

    Children of any age are allowed.
    Children up to and including 2 years old stay for free when using an available cot.
    Children up to and including 8 years old stay for free when using an existing bed.
    Children up to and including 8 years old stay for free when using an available extra bed.
    People 9 years old and over stay for US$45 per person per night when using an available extra bed.
    Any type of extra bed or child's cot/crib is upon request and needs to be confirmed by management.
    Supplements are not calculated automatically in the total costs and will have to be paid for separately during your stay.

Location

Guest Reviews

9.6
Based on 572 reviews
Cleanliness: 8.49
Service: 9.96
Location: 10
Room Quality: 9.45
Amenities: 9.48
Value for Money: 9.44
Food and Beverage: 9.99
Overall Experience: 10
A
amanda • solo_traveller • us
10
Cozy, incredible, delicious. One of (if not the) best places I've ever stayed.
Pros:

The complimentary breakfast is insane! SO delicious and high-end, I plan to stay here at least five more times just to try everything haha But really, this place is nothing short of amazing. The staff, the fresh baked cookies and ice in the room waiting for me, the spa tub, the windows overlooking the city, the boujee feel of the decor, the awesome old staircase leading to my room, absolutely everything about this place is incredible. I am planning another trip to Ashland just to stay here again, it was that awesome. I hope this place and other unique places like it stay in business a very long time.

Cons:

I have zero complaints, I will say the main door key didn't work that well and I kept having to try and retry opening it, but the staff knows this and I'm sure they will fix it, they obviously pay attention to the needs of the building.

2026-03-06 • via Nuitee
S
Susan • couple • us
10
Excellent breakfast and super nice staff!
Pros:

Wonderful property! Everything top notch.
Last minute pricing was a blessing.

Cons:

Comfy, well supplied, quaint !

2026-03-02 • via Nuitee
B
Bonita • couple • us
10
A not to miss lodging experience in Ashland.
Pros:

Lovely property and gracious staff. Extra touches such as cookies in the room, ice in ice bucket, phone call to relay room was ready for early check in. Complimentary breakfast was fabulous!

2026-02-24 • via Nuitee
S
Sue • couple • us
10
Pros:

The free breakfast was a culinary delight!
Off season prices were extremely reasonable.

2026-02-22 • via Nuitee
K
Kevin • solo_traveller • us
10
Pros:

Extra touches, cookies at 3:00PM. Good washing accessories

2026-01-30 • via Nuitee
J
Janet • couple • us
10
Pros:

Everything!

2026-01-27 • via Nuitee
E
Eartha • couple • us
8
2026-01-25 • via Nuitee
M
Martin • couple • au
8
Thoroughly recommend this property for an overnight stop.
Pros:

Charming location with well appointed rooms. Huge breakfast.

Cons:

Pillows were a bit soft for our liking.

2026-01-24 • via Nuitee
N
Nancy • couple • us
8
Memorable inn with amazing breakfast. Great location to walk downtown. But you’re kind of on your own after 5 pm in wint
Pros:

Great historic inn with period furnishings. Great location to walk downtown. Breakfast is amazing!!!!!

Cons:

Carpet needs replacing. No staff around after 5:00 p.m., at least in winter.

2026-01-22 • via Nuitee
E
Eleanor • couple • us
10
Lovely room, with fabulous, attached restaurant and bar. Top location. Very classy. Treat yourself!
Pros:

The room was spacious. We had a room with a king bed and an extra single bed, and a large sitting area. Bathroom was spacious and clean with robes for lounging. The breakfast that was included was fabulous. We have stayed here many times. The bar was great and we also had dinner here one night which was a highlight for us. The staff is also extremely friendly and helpful.

Cons:

We don't have any complaints.

2026-01-20 • via Nuitee
A
Alexa • couple • us
9
Winchester is well appointed, great downtown location, and generous amenities
Cons:

The breakfast was disappointing. My meal arrived cold.

2026-01-20 • via Nuitee
A
amada • couple • us
10
Delightful
Pros:

The location was good and the property itself was beautiful. Our bed was very comfortable and our room was oversized and very clean. The breakfast was amazing.

2026-01-19 • via Nuitee
C
Claire • couple • us
10
2026-01-19 • via Nuitee
A
anna • couple • us
5
Not what i expected.
Pros:

Great location. Friendly staff and good breakfast!

Cons:

It’s very old. Creaky floor, full carpet and small room.

2026-01-19 • via Nuitee
W
Wendy • couple • us
6
Since my husband could have wound up eating walnuts was unacceptable. And there was no effort to.
Pros:

My husband had a recorded walnut allergy, and the staff delivered cookies with walnuts. Luckily, I noticed before he ate one. This could have been horrible. They did not offer us anything to replace it. Very disappointing and could have had serious consequences! Also, the bathroom door did not shut.

Cons:

I got these backwards. See above for dislike. What we enjoyed was the location. The breakfast was deliciius

2026-01-19 • via Nuitee
K
Kristy • extended_group • mx
10
I would stay at the Winchester each time I was in Ashland, if I could. No better place around!
Pros:

I've stayed at the Winchester many times in the past. This trip was much like the others. The room was sparkling clean. The Breakfast was the best breakfast you could get, which is included in the room price. A fabulous choice on the menu. In the room there are great little things waiting for you like, home made cookies, which are amazing; a variety of teas; coffee and a bottle of wine (which you pay for). We couldn't ask for anything more on top of the beautiful grounds and the antique environment, you might expect a horse & carriage to come pick you up.

Cons:

I liked everything, I must admit!

2026-01-17 • via Nuitee
M
Matthew • couple • us
10
This is our third time here. We will be back
Pros:

Location is excellent, right in the middle of town. Able to walk to most things. The breakfast is outstanding.

Cons:

We liked everything

2026-01-13 • via Nuitee
C
Cathompson5 • Couples • Medford, Oregon
10
Truly enjoyable
Pros:

The bed and the pillows are incredibly comfortable. It’s difficult to get out of bed in the morning, but worth it for the breakfast that is insanely good. Portions for the breakfast are amazing and the taste is really exceptional. We love everything about this place and have stayed a few times now. Everyone is really kind, check-in is really easy, location is perfect.

2026-01-10 • via Tripadvisor
T
Ted • couple • us
9
Pros:

Charming place, wonderful people, really good food.

2026-01-10 • via Nuitee
K
Kyra • couple • us
10
A gem in the off season!
Pros:

Outstanding breakfast, lovely grounds, loved the fireplace in our room. Off season it’s a great deal and wonderful place to stay. Wouldn’t be able to experience this place in high season.

Cons:

Only complaint we had was the plethora of placards in the room. Putting all the instructions, menus etc would have been been much nicer in a nice book.
Would be nice if could encourage other guests not to slam their doors. You wouldn’t think you’d need to tell people to be considerate but seems it’s needed.

2026-01-10 • via Nuitee