Free
Children allowed

Facilities

WiFi available
Free WiFi
Parking
Free Parking
Non-smoking rooms
Air conditioning
Restaurant
Heating
Family rooms
Garden
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.
A deposit may be required at the property.

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 628 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
E
Edward couple it
9
Lovely victorian-style inn close to the Ashland theatres.
Pros:

This is a top-notch property in Ashland, we've visited multiple times before. It's close to the theatres. The breakfasts are very good. The furnishings are largely in an antique style.

Cons:

The breakfast, while free, is full of premium offerings that are not. You are presented every day with a strangely computed bill (with a credit for a free breakfast) to which you are asked to add a tip. I would prefer being asked to add a cumulative tip at check-out. Rooms haven't been updated in a while.

2026-07-24 via Nuitee
N
Nina couple us
10
Very pleasant stay in a very comfortable room; very attentive staff.
Pros:

Nicely served breakfast ordered from a menu. Wait staff was excellent. Didn't expect the $5 charge for the coffee at breakfast.

Cons:

Although it was not an issue for me, I would advise anyone that has mobility issues that there are stairs and hills on the property (no elevator).

2026-07-22 via Nuitee
T
Timothy couple us
10
2026-07-22 via Nuitee
L
Lloyd solo_traveller us
10
2026-07-21 via Nuitee
M
Marianne couple us
10
Beautiful stay in the heart of it all
Pros:

Great location and staff. Comfortable room and amazing breakfast. They even left ice and a treat in the afternoon, which made a huge difference.

2026-07-16 via Nuitee
K
Kathy extended_group us
9
2026-07-16 via Nuitee
S
Sheppard couple us
10
2026-07-16 via Nuitee
M
Marianne couple us
10
2026-07-16 via Nuitee
A
Amanda couple us
9
2026-07-15 via Nuitee
T
Ted solo_traveller us
10
Pros:

Charming place with wonderful staff.
So convenient and comfortable.
Rooms exceptionally well done and nice amenities.

Cons:

Dinner at chateaubriand 36 disappointing.
Very slow service, uncooked food, just can't risk going back.

2026-07-14 via Nuitee
M
Michelle couple us
10
We felt swaddled in luxury. I cannot imagine a better way to get away, see theater and relax.
Pros:

The English Gardens, the dining area, the rooms, the location-they were all stunning!

2026-07-13 via Nuitee
L
Lisa couple us
10
Lovely historic inn in a perfect location
Pros:

The property has a quaint, historic charm, yet offers up to date comforts (great bedding, nice bathroom, comfortable sitting area). Lots of nice little touches in the room, and the gardens are lovely. Our stay included a delicious breakfast with a variety of options. We were only here for one night, and I have a feeling that more nights would have made it even better, to have more time to settle in and really take advantage of what the inn has to offer. This is an ideal location for attending the Shakespeare festival -- the theaters are a five-minute walk from the inn, as is the rest of the main shopping/dining area of Ashland.

Cons:

Possibly nitpicky, but there were instruction sheets and signs on practically every surface of the room -- what to touch, what to use, what not to do, etc. It was too much! Also, the honor bar in the room isn't clear enough -- we first went to put our drinks and supplies in the fridge and were happy to see cold bottled water already there. Took us a minute to find the sign with the prices. Good thing we looked around before helping ourselves!

2026-07-13 via Nuitee
A
Andrea couple us
7
2026-07-11 via Nuitee
I
Indrajit couple us
10
An English cottage with luxe touches. Really special
Pros:

The inn is gorgeous and incredibly well maintained. The little flourishes-like delicious hand made treats from the pastry check left at the room every day—bring it a level of luxury and refinement far above its price point. From the incredible included breakfast every morning to the fabulous happy hour bar, the vide is serene and the venues are exceptional.

Cons:

Nothing at all to complain about!

2026-07-09 via Nuitee
I
Indrajit couple us
10
No better hotel in southern Oregon
Pros:

Incredible location, gorgeous large comfy rooms, insanely good breakfasts

Cons:

Everything great!

2026-07-09 via Nuitee
N
Natalia couple us
9
Charming Historic Inn in the Perfect Location
Pros:

We stayed at the Winchester Inn for one night and thoroughly enjoyed our visit. The location is perfect—within easy walking distance of downtown Ashland, restaurants, and shops.

Our room was very comfortable and had a lovely old-world charm that gave the inn a warm and welcoming atmosphere. It was a wonderful blend of historic character and modern comfort.

We would definitely stay here again and highly recommend the Winchester Inn to anyone visiting Ashland.

Cons:

N/A

2026-07-02 via Nuitee
E
Eden couple us
10
2026-07-02 via Nuitee
P
Patricia couple us
10
Great location, charming boutique hotel.
2026-07-02 via Nuitee
E
Eden couple us
10
2026-07-02 via Nuitee
P
patj239 Couples Gig Harbor, Washington
10
Fantastic B&B
Pros:

This our second stay here. We will be back. It is awesome B&B. The location is great, easy walk to the theaters. The breakfasts are very good with variety of choice.

2026-07-01 via Tripadvisor