Winchester Inn
Hotel, 5-star35 South 2nd Street, Ashland, OR, United StatesShow on map
Exceptional
One of our highest-scored stays, according to its guests.
9.6659Reviews- Check-in from 4:00 PMCheck-out by 11:00 AM.
- Exceptional locationGuests rate the location 10.0 out of 10, at 35 South 2nd Street.
- Free parkingThe property states parking on site is free for guests.
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!
What this place offers
- WiFi available
- Free WiFi
- Parking
- Free Parking
- Non-smoking rooms
- Air conditioning
- Restaurant
- Heating
- Family rooms
- Garden
Rooms
9.6
Exceptional
Rated 9.6 out of 10 by 659 guests who stayed here.
- Cleanliness8.5
- Service10.0
- Location10.0
- Rooms9.4
- Amenities9.5
- Value9.4
- Food & drink10.0
Guests mention
Charming locationAmazing breakfast
MichaelUnited StatesWhat a delight!
Everything about the property--and I mean everything!--was top notch and exceptional: the welcome, the room, breakfast, housekeeping, historic architecture, landscaping, location. We love the place and will make it part…
KathyUnited StatesWonderful stay in Ashland.
The room had nice morning light, large windows, a comfortable king bed and a large bathroom. We loved having the balcony. Breakfast was excellent.
The room was on the second floor and if you aren't good with stairs,…
HarryUnited StatesGreat place to stay if you are attending the Oregon Shakespeare Festival.
Small, quiet and very convenient to the theaters. Helpful and considerate staff. Excellent restaurants.
Very high bed that could be a challenge to get in and out of.
JoelUnited StatesA Two-night Stay in a 5-star Hotel
From the staff to the facility, this rates as a 5 Star hotel. I plan to make this my go-to hotel for future visits.
While I gave this the highest possible rating, the bed and sofa bed were very uncomfortable. The main…
DeniseUnited StatesSpectacular accommodations, service and food. Highly recommend.
The dinner and breakfast were outstanding. All of the staff were amazing, kind and professional.
Nothing!
RossUnited StatesGreat location, nice facility and excellent staff.
The breakfast and service were good, but a little more variety day to day would be appreciated.
The room size and location were very good for our needs.
The room, the family suite off the driveway was well appointed,…
Reviews are written by guests who booked through our supplier and stayed, shown as written and in their own language. Category scores are the supplier’s reading of recent reviews, updated January 2026.
Where you’ll be
35 South 2nd Street, Ashland, OR, United States
Guests rate the location 10.0 out of 10 — exceptional.
Things to know
Cancellation
Each room shows its own terms before you pay.
Most rates can be cancelled free until a date shown on the room.
Non-refundable rates are marked as such.
House rules
Check-in from 4:00 PM
Check-out by 11:00 AM
Children welcome
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No pets
Free parking on site
Non-smoking rooms available
Payment & property
Paid when you book, not at the desk.
Rates include the taxes and fees we can read.
The property may take a card at check-in for incidentals.
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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.
What we’d check for you here
- How many rooms they will hold at once, for how long, and on what terms.
- That the step-free room is actually free on your dates, and whether it is a roll-in shower or a bath, which the listing never says.
- Whether there is room for a pickup, a trailer or a van, not just a car.
- Whether breakfast is in the rate or added at checkout, and what time it runs.
- Whether the rate moves for your dates, and what it includes.
- What the property actually charges at the desk on top of the rate.
Questions about Winchester Inn
What time is check-in and check-out at Winchester Inn?
Check-in is from 4:00 PM. Check-out is by 11:00 AM. If you're arriving late, tell us and we'll ask the property to hold the room.
Does Winchester Inn allow pets?
No — the property states that pets are not allowed.
Is there parking at Winchester Inn?
Yes — the property states that parking on site is free. Whether a space can be reserved in advance varies, so we check it against your dates.
Is breakfast included at Winchester Inn?
Breakfast is offered at the property. Whether it's included depends on the rate — the board type is shown on each room once you put your dates in.
Does Winchester Inn have Wi-Fi?
Yes — internet access is listed among the property's facilities.
Can I book a block of rooms at Winchester Inn?
The property lists meeting and banquet space, which usually means it handles group business — but how many rooms it will hold at once, for how long, and at what rate are set case by case and are not in any feed. Tell us the dates and the number of rooms and we'll get those terms from the property in writing before anything is charged.
Does Winchester Inn have wheelchair accessible rooms?
The property lists step-free or accessible facilities. That flag is the one least able to settle the question: a hotel can carry it and still have a step at the entrance, or a bath rather than a roll-in shower, and it does not say whether the accessible room is free on your dates. Tell us what you need and we'll ask the property directly rather than reading you the flag.
How do I book Winchester Inn?
Put your dates in above and book online, or call (888) 789-8585 and we'll do it for you — including things a booking form can't handle, like a block of rooms, a monthly rate or an invoice for your employer.
Where is Winchester Inn?
35 South 2nd Street, Ashland, OR.
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