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Best Western Windsor Inn

AAA - 3 Diamond

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Stay at this Ashland, Oregon hotel offering convenient access to the Shakespeare Festival, Southern Oregon University and the Mount Ashland Ski Resort.

Conveniently located right off the Interstate 5 in Southern Oregon, the Best Western Windsor Inn offers comfortable accommodations, full-service amenities and unbeatable customer service at an affordable price. This Ashland hotel boasts 91 recently remodeled guest rooms including suites and Jacuzzi rooms. Each room features cable television and high-speed Internet access for guests convenience. Enjoy an array of amenities including a delicious complimentary full breakfast, the largest outdoor swimming pool in Southern Oregon, year-round outdoor hot tub, exercise facility, limited business services and meeting facilities accommodating up to 250 guests. Pets are welcome!

The Best Western Windsor Inn is only about a five minute drive from downtown Ashland, which offers a variety of shops and restaurants. The Best Western Windsor Inn is the perfect way to enjoy a quiet and relaxing stay in Ashland. We are far enough away from the hustle and bustle of Ashlands downtown area--but still conveniently located to the best Ashland has to offer. Relax outside among our rose gardens and enjoy the views of the surrounding Ashland Hills and Siskiyou mountains. See a Shakespearean play at the Oregon Shakespeare Festival, the largest rotating repertoire theater, or spend the afternoon at Lithia Park walking the many trails. During the summer months enjoy rafting down the Rogue River, while in the winter Mount Ashland offers fantastic skiing. Other nearby attractions include Southern Oregon University, Emigrant Lake and historic Jacksonville, Oregon.

The friendly, helpful staff at the Best Western Windsor Inn is ready to ensure a fun-filled memorable stay in Ashland, Oregon. Make a reservation today and save! Enjoy your stay.

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2520 Ashland Street
United States
AAA - 3 Diamond


Pets: No Pets accepted
Check-in & Check-out
15:00:00 | 11:00:00


Location and Attractions

Getting there.

Sat nav users: type 97520-1412

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2520 Ashland Street
United States

What's nearby?


  • 15.00 mile(s) from Medford

  • 19.50 mile(s) from Jacksonville

  • 45.00 mile(s) from Grants Pass

  • 50.00 mile(s) from Yreka

  • 2.00 mile(s) from Southern Oregon University

  • 14.90 mile(s) from Rogue Community College

Room Theatre Classroom U-Shape Boardroom Banquet
Have an enquiry?
Contact events on 0845 620 0506


TripAdvisor Traveller Rating: Rating: Based on 936 traveller reviews
Rating: 5 529
Rating: 4 303
Rating: 3 69
Rating: 2 22
Rating: 1 13

Large and comfortable room

26/06/2017 Alex C,

Our room was large and comfortable. The beds were comfortable and the plethora of pillows was welcome. We used the laundry and we swam, while waiting for the laundry to finish. It was a good afternoon... more


Nice suprise in Ashland

26/06/2017 Andrea A, portland, United States

Coming back from 3 weeks on the road back to Portland we stopped at the Windsor Inn. It is one of the nicest Best Westerns I have stayed at. I normally don't go in the pool but this was inviting. D... more


convenient, comfortable, charming

26/06/2017 Don R, Kirkland, United States

Lovely grounds, very friendly and helpful staff. Enjoyed being able to walk to dinner (Caldera Brewing around the corner). Great stop for the first night of a road trip. Great value for the accomod... more


Fantastic Value

25/06/2017 Travelnista, San Jose, California

We've stayed here twice and will stay again. This is a very nice motel with beautiful views, great pool area and good breakfast. The rooms are spacious, clean, and seem recently renovated. Beds are co... more

Owner Response
AshlandWindsor, Guest Relations Manager at Best Western Windsor Inn, responded to this review
Dear Guest, Thank you so much for writing such a wonderful review of your most recent stay. It is great to hear that you enjoyed the beautiful views, great pool area, our full hot breakfast, and that you received a "fantastic" value! We appreciate your continued business, and hope to see you again next time you're travelling through the area. Sincerely, Chloe Guest Relations

Great Stay

21/06/2017 Sirilo G, Long Beach, California

Stayed 5 days. Great place to stay. Right off the 5 Fwy. Just minutes from downtown Ashland. Clean hotel/property. Excellent free breakfast with minor changes to menu daily. Friendly staff. Free Wi-Fi... more

Owner Response
AshlandWindsor, Guest Relations Manager at Best Western Windsor Inn, responded to this review
Dear Guest, Thank you for providing feedback from your recent five night stay. I am so happy to hear that the room was clean, the bed was comfortable, our staff was friendly, and that you enjoyed our full hot breakfast. We look forward to your future stays with us. Sincerely, Chloe Guest Relations