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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
  • Low rate guarantee
  • Free WIFI
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Rooms & Rates


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
TripAdvisor Traveller Rating: Rating: Based on 848 traveller reviews
Rating: 5 462
Rating: 4 286
Rating: 3 67
Rating: 2 21
Rating: 1 12

It was ok

15/02/2017 Shanna R, Madera, California

Clean, quiet, easy access to the freeway and to grocery stores. The hotel looks nice, it is clean, the rooms are clean. The check in was less than pleasing and check out was just awful. The only p... more

Owner Response
AshlandWindsor, General Manager at BEST WESTERN Windsor Inn, responded to this review
Dear Shanna R, Thank you for your review. I really appreciate you taking the time to let me know about your stay! I'm glad that the stay was clean and quiet for you, and I apologize about the customer service issues you experienced. I'll be using your feedback to work with the staff members you mentioned to improve on our customer service skills so we can provide superior service to all of our guests! I hope you give us another chance to impress you on your next trip through town. If you would like, I would be happy to discuss your stay further with you. Please give me a call at 1-800-334-2330 or email me at info@windsorashland.com. Sincerely, Jessie Karlovich General Manager

Great value, excellent breakfast.

14/02/2017 susanaaronb, Yreka, California

This hotel was very clean, enjoyed our stay. The breakfast was one of the best complimentary hotel breakfast I have had and I have stayed at numerous hotels for work and pleasure. It is a convenient ... more


Great value, tasty breakfast included, extremely friendly & helpful staff

13/02/2017 Joe_from_CO, Ithaca, NY

This the second time we've stayed here for a ski trip to Mt. Ashland. The value is hard to beat -- with an included hot buffet breakfast with a wide variety including eggs, waffles, pancakes, sausage ... more



12/02/2017 758kayp, Portland, Oregon

Room was very clean and quiet! Staff very friendly and accommodating. Check in was very quick and efficientt. Breakfast was good and many selections to choose from. Would stay here again if in Ashla... more


Best Western Windsor Ashland review

06/02/2017 Franklin F, Auburn, Washington

Nice clean hotel, great service nice location. Note, if you use google to find the hotel, it routes you through Ashland. Stay on the freeway to the last Ashland exit to find the hotel. The breakfast w... more