Hotel, 3-star2520 Ashland Street, Ashland, OR, United StatesShow on map
Guests rate it highest for service, location and value.
8.8853ReviewsEnglish Tudor-style Architecture: Step into a charming world of English Tudor-style architecture at Best Western Windsor Inn in Ashland, Oregon. The distinctive design sets the tone for a unique and memorable stay.
Modern Amenities: Enjoy modern comforts in our contemporary rooms, complete with a cable TV, refrigerator, and coffee machine. Stay cool with air conditioning and relax in a private bathroom with complimentary toiletries.
Relaxation and Convenience: Unwind in the outdoor swimming pool and hot tub, or explore the colourful rose gardens. Stay on top of work at the business centre. With the Oregon Shakespeare Festival just a short drive away, Best Western Windsor Inn offers the perfect blend of relaxation and convenience.
Ready to experience the charm and comfort of Best Western Windsor Inn? Book your stay now and make unforgettable memories in Ashland, Oregon.
8.8
Rated 8.8 out of 10 by 853 guests who stayed here.
The room and the whole facility was clean and well taken care of. Ryan, at the front desk was very knowledgeable and helpful, though grumpy.
The light in the bathroom was very low. Better lighting would have been better…
that my dog had a place to go potty
didn’t have time to use the pool
Comfortable bed, quiet room and good breakfast.
Good location, good parking, comfortable bed. Good breakfast options, pool
Refrigerator froze my food!
Very clean and well kept, a decent look and hot tub. We had a spacious room with a fridge. The staff were all pleasant and helpful.
Lovely room
Shower curtain rod poorly installed. Shower curtain kept slipping to the middle.
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.
2520 Ashland Street, Ashland, OR, United States
Guests rate the location 9.6 out of 10 — exceptional.
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.
Check-in from 3:00 PM
Check-out by 11:00 AM
Children welcome
No pets
Free parking on site
Non-smoking rooms available
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.
Please note that the property does not have elevators. Please let the Best Western Windsor Inn know your floor preference when booking by using the Special Requests box.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. A deposit may be required at the property.
Check-in is from 3:00 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.
No — the property states that pets are not allowed.
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.
Yes — a pool is listed among the property's facilities. Seasonal closures are common, so we'll confirm it's open for your dates.
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.
Yes — internet access is listed among the property's facilities.
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.
The property lists a front desk staffed 24 hours, so a late arrival should be possible. Standard check-in is from 3:00 PM. Rooms are still released after a cut-off at some properties regardless of the desk hours, so tell us your arrival time and we'll have them hold it.
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.
2520 Ashland Street, Ashland, OR.
Nothing to do with the booking above. The same market, priced the same way, for if this one is not it.