Skip to main content
  1. Hotel reviews homepage
  2. US hotel reviews
  3. Oregon hotel reviews
  4. Ashland hotel reviews
  5. Reviews of Best Western Windsor Inn

Reviews of Best Western Windsor Inn This rating is a reflection of how the property compares to the industry standard when it comes to price, facilities and services available. It's based on a self-evaluation by the property. Use this rating to help choose your stay!

2520 Ashland Street, Ashland, OR 97520, United States

#9 of 22 hotels in Ashland

Guests' Choice

Review Score

Based on 513 hotel reviews

8.6

Score breakdown

  • Cleanliness

    9.1

  • Comfort

    9.1

  • Location

    9.0

  • Facilities

    8.7

  • Staff

    9.4

  • Value for money

    8.7

  • Free Wifi

    9.0

Verified guest reviews from real Bookers

Real Bookers. Real stays. Real opinions.

Read more– opens a dialog box
Write a Review

Showing 1 - 25

  • Reviewed: September 4, 2025

    10
    Exceptional
    • Leisure trip
    • Group
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night
    • Submitted from a mobile device

    Location and breakfast

    Stayed in August 2025

  • Reviewed: August 31, 2025

    8.0
    "There golden sleep doth reign"
    • Leisure trip
    • Couple
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 4 nights

    Would prefer: regular coffeemaker over wasteful Keurig, refillable toiletries rather than single-use plastic bottles, a microwave in room would have been nice but no big deal as one in dining area is available. Ground floor 111 was good but pretty annoyed that we could not un-hear the rhythmic sounds of romance in the room above us late one night :- (

    Very good hot breakfast with lots of offerings (and real silverware!), wonderful dining room attendant Leticia who works hard, always has a smile and a greeting; good pool, comfortable king bed, Direct TV has TCM and good channels that we like, double sinks in bath area are great, good seating with nice upholstered bench, two upholstered chairs, a dining table, a desk with swivel chair, a good amount of layered lighting in the room, appreciate the clock radio and plentiful electrical outlets in table lamps, good quality wi-fi. Also appreciate the laminated cards with hotel information and TV channels in the room. All-in-all, a convenient place to stay to attend OSF plays and Ashland activities. While not in the central city, it's an easy drive from the hotel to the buzz of the plaza.

    Stayed in August 2025

  • Reviewed: August 30, 2025

    10
    Great accommodation in Ashland
    • Leisure trip
    • Couple
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night
    • Submitted from a mobile device

    Good location, plenty of parking, very comfortable bed

    Stayed in August 2025

  • Reviewed: August 29, 2025

    8.0
    Great place for pets
    • Leisure trip
    • Family with young children
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night
    • Submitted from a mobile device

    The rooms could use some updating, but they are still spacious, clean, and comfortable.

    Staff was very helpful and friendly. The grassy dog area was beautiful. The room was spacious. The bed was comfortable.

    Stayed in August 2025

  • Reviewed: August 28, 2025

    10
    A perfect place to stay.
    • Couple
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night
    • Submitted from a mobile device

    The check-in was easy and the staff helpful and friendly. The room was in a perfect location, especially for my handicapped husband. The actual room was very clean and comfortable. The breakfast area was roomy and the variety of food was excellent. We thoroughly enjoyed our stay!

    Stayed in August 2025

  • Reviewed: August 27, 2025

    10
    We would certainly stay here again. I felt like a luxury hotel with a reasonable price.
    • Family with young children
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night
    • Submitted from a mobile device

    It was hard to find something we didn't like. We did notice there was not a microwave in the room.

    Well-appointed rooms. Pleasant employees. Comfortable bed and pillows, quiet night's rest. Breakfast was great with much to choose from.

    Stayed in August 2025

  • Reviewed: August 23, 2025

    10
    Fantastic, best stay this year.
    • Leisure trip
    • Family with young children
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night

    The room is equipped with a standard height toilet. Traveling seniors would especially enjoy having a higher rise (17 inch seat) model. We have 3 of the 17 inch units at home which makes our rising to a standing position much easier. Our experieance is that the cost premium for such a unit is very small compare to the comfort recieved.

    We have traveled to many places in the USA, usually staying at publicly available lodging. The staff was friendly and quick to offer suggestions and answer any questions. The facilities were clean, well-kept, and comfortable. Breakfast was an ample offering of well-prepared eggs, bacon and pastries. The coffee was good too. The location was near I5 freeway, yet incredibly quiet. This is our top-rated offering after several years of travel.

    Stayed in August 2025

  • Reviewed: August 21, 2025

    10
    Convenient, comfortable and wonderful staff.
    • Leisure trip
    • Couple
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 6 nights

    Nothing I can think of. Always stay here when I come to Ashland.

    Great helpful staff, easy check-in and checkout, good location, clean room.

    Stayed in August 2025

  • Reviewed: August 16, 2025

    10
    I will return again
    • With a pet
    • Leisure trip
    • Solo traveler
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night

    Very congenial staff at the desk when I arrived and in the breakfast dining room. The pet relief area was wonderful!!!! Also, I loved the pet care package I received when I arrived. The room was very clean and superb!!!

    Stayed in August 2025

  • Reviewed: August 12, 2025

    8.0
    Very Good
    • Leisure trip
    • Couple
    • King Suite with Kitchen - Non-Smoking
    • Stayed 1 night

    The AC got problem

    Location, private and safe

    Stayed in August 2025

  • Reviewed: August 10, 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • Queen Room with Two Queen Beds - Non-Smoking/Pet-Friendly
    • Stayed 1 night
    • Submitted from a mobile device

    The guy at the front desk was particularly charming

    Stayed in August 2025

  • Reviewed: August 5, 2025

    9.0
    Charming, comfortable and near a supercharger and brewery
    • Leisure trip
    • Couple
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night

    The property has undeniable charm with its half-timbered façade and beautifully mature landscaping. Despite being close to the freeway, it feels like a peaceful oasis. We slept with the windows open instead of using the AC, and while we could faintly hear the freeway in the distance, the sound was soft and far less intrusive than the hum of the air conditioner. One of the greatest perks is the Tesla Supercharger located right next to the hotel - an incredibly convenient feature for EV drivers. Also next door is the Caldera Brewery, which serves a solid selection of beers, including some good sours.

    Stayed in July 2025

  • Reviewed: July 30, 2025

    10
    Very helpful staff, beautiful stay
    • Leisure trip
    • Group
    • Queen Room with Two Queen Beds - Disability Access/Non-Smoking
    • Stayed 1 night
    • Submitted from a mobile device

    Nothing

    Beautiful landscaping, really good breakfast

    Stayed in July 2025

  • Reviewed: July 29, 2025

    10
    It was relaxing and beautiful
    • Leisure trip
    • Family with young children
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night
    • Submitted from a mobile device

    No complaints

    Nice architecture and pool was great. Grounds were clean and well maintained.

    Stayed in July 2025

  • Reviewed: July 24, 2025

    10
    We were impressed.
    • Leisure trip
    • Family with young children
    • Queen Room with Two Queen Beds - Non-Smoking/Pet-Friendly
    • Stayed 1 night
    • Submitted from a mobile device

    We thought it was very impressive place to stay. It was beautiful and well maintained. The breakfast area was huge, loved that. Nice pool and hot tub. Room was clean and spacious. We will be back.

    Stayed in July 2025

  • Reviewed: July 23, 2025

    8.0
    Comfortable Stay with Good Amenities
    • Leisure trip
    • Group
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night

    Minor issues - Drip coffee at morning breakfast was a bit watered down. Gym dumbbells (fairly standard across hotel chains) are non existent, but lifting machines and treadmill are good enough.

    Friendly staff at check in and breakfast. Clean rooms. Comfortable beds. Plenty of parking. Good location to hit up a show in town. Large gym with plenty of open space for working out. Overall, a good overnight stay while road tripping to Portland. A bit pricey for a class level of hotel, but a good place to stay if can be booked on discount.

    Stayed in July 2025

  • Reviewed: July 7, 2025

    8.0
    Clean older facility that was unfortunately what we expected
    • Leisure trip
    • Couple
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night
    • Submitted from a mobile device

    Our door wouldn’t stay closed without using the deadbolt. The bed felt very used, kinda sank in areas. Parking was very tight for our large truck. Ice machine was broken. Lighting was dim in our room. Very expensive considering the basic room.

    Friendly helpful staff. Good location. Relatively quiet

    Stayed in July 2025

  • Reviewed: July 3, 2025

    8.0
    Very Good
    • Leisure trip
    • Family with young children
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night
    • Submitted from a mobile device

    The unit was nice and spacious. We had a small issue with the A/C, but nothing major. We also found a beer bottle cap on the rug near our bed. Otherwise we enjoyed our short stay there

    Stayed in July 2025

  • Reviewed: June 21, 2025

    10
    It was a perfect overnight rest for after a very long drive.
    • Leisure trip
    • Couple
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night
    • Submitted from a mobile device

    The pool was great for swimming laps!

    Stayed in June 2025

  • Reviewed: June 21, 2025

    9.0
    Great location
    • Leisure trip
    • Solo traveler
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night

    Great location for travelers.

    Stayed in May 2025

  • Reviewed: June 17, 2025

    9.0
    Good stay
    • Leisure trip
    • Solo traveler
    • Queen Room with Two Queen Beds - Non-Smoking/Pet-Friendly
    • Stayed 7 nights
    • Submitted from a mobile device

    Numerous outlets did not work. Also the comforters slide off the bed so difficult to use.

    Breakfast good. Nice place to stay

    Stayed in June 2025

  • Reviewed: June 11, 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • Queen Room with Two Queen Beds - Disability Access/Non-Smoking
    • Stayed 1 night
    • Submitted from a mobile device

    Location, front desk staff, pool, breakfast.

    Stayed in June 2025

  • Reviewed: June 10, 2025

    10
    Very clean and comfortable!
    • Leisure trip
    • Family with young children
    • King Suite with Wet Bar - Non-Smoking
    • Stayed 1 night
    • Submitted from a mobile device

    The only thing I think needs improvement was the bed. It was not very comfortable, and I could feel the springs.

    The room was very clean and stocked. I liked how the bedroom has its own door and the bathroom was located outside of the bedroom. The plugs were easily accessible and the air conditioner was awesome.

    Stayed in June 2025

  • Reviewed: June 8, 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • King Room - Non-Smoking/Pet-Friendly
    • Stayed 1 night

    Excellent breakfast.

    Stayed in May 2025

Showing 1 - 25

We Price Match
We Price Match
Low rates • No booking fees • Find something cheaper? We'll refund the difference!

Guests also reviewed these properties: