Best Western Windsor Inn
Hotel, 3-star2520 Ashland Street, Ashland, OR, United StatesShow on map
Fabulous
Guests rate it highest for service, location and value.
8.8853Reviews- Check-in from 3:00 PMCheck-out by 11:00 AM. The front desk is staffed around the clock, so a late arrival is fine.
- Exceptional locationGuests rate the location 9.6 out of 10, at 2520 Ashland Street.
- Free parkingThe property states parking on site is free for guests.
English 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.
What this place offers
- Fitness facilities
- WiFi available
- Free WiFi
- Parking
- Free Parking
- Non-smoking rooms
- Air conditioning
- Fitness center
- Swimming pool
- 24-hour front desk
Rooms
8.8
Fabulous
Rated 8.8 out of 10 by 853 guests who stayed here.
- Cleanliness8.6
- Service9.6
- Location9.6
- Rooms8.6
- Amenities8.1
- Value9.1
- Food & drink8.1
Guests mention
Friendly staffClean roomsGood location
MaryUnited StatesWe love Ashland and have stayed here before so we knew it would be just fine.
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…
EdithUnited Statesnice place to stay
that my dog had a place to go potty
didn’t have time to use the pool
StevenUnited StatesComfortable bed, quiet room and good breakfast.
RebeccaUnited StatesGood location, good parking, comfortable bed. Good breakfast options, pool
Refrigerator froze my food!
JudithUnited StatesVery 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.
PatUnited StatesLovely 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.
Where you’ll be
2520 Ashland Street, Ashland, OR, United States
Guests rate the location 9.6 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 3:00 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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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.
What we’d check for you here
- 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.
- That the desk is staffed when you land, and that the room is held past cut-off.
- The pet fee and any size limit, which is where these bookings usually come apart.
- 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 Best Western Windsor Inn
What time is check-in and check-out at Best Western Windsor Inn?
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.
Does Best Western Windsor Inn allow pets?
No — the property states that pets are not allowed.
Is there parking at Best Western Windsor 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.
Does Best Western Windsor Inn have a pool?
Yes — a pool is listed among the property's facilities. Seasonal closures are common, so we'll confirm it's open for your dates.
Is breakfast included at Best Western Windsor 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 Best Western Windsor Inn have Wi-Fi?
Yes — internet access is listed among the property's facilities.
Does Best Western Windsor 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.
Can I check in late at Best Western Windsor Inn?
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.
How do I book Best Western Windsor 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 Best Western Windsor Inn?
2520 Ashland Street, Ashland, OR.
Other places we book in Ashland
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