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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 885 traveller reviews
Rating: 5 492
Rating: 4 291
Rating: 3 69
Rating: 2 21
Rating: 1 12

Simple, clean, affordable!

26/04/2017 thefourwalls805, Templeton, California

Needed a place to overnight that was affordable and found the Best Western Windsor Inn the right choice. The staff was great, room was clean, and location convenient. Downtown Ashland was a 5 minute d... more


Who knew? Outstanding room at decent price.

24/04/2017 Douglas L, San Diego, California

Ashland is on I-5, but it's not the de riguer stop. Somehow it became so for my wife and I. This Best Western was wonderful. Others were staying there by the time we arrived, but there was a host of o... more


Nice stay

23/04/2017 72Gianna, Bend, Oregon

Well located, comfortable, clean, caring staff. Easy access to downtown Ashland with its many good restaurants to choose from. Parking is an issue especially when attending plays at the Shakespeare Fe... more

Owner Response
AshlandWindsor, Guest Relations Manager at BEST WESTERN Windsor Inn, responded to this review
Dear Gianna, Thank you for choosing to stay with us during your recent trip to Ashland. I am so happy to hear that our location was convenient for you while you were attending the Shakespeare Festival. I also appreciate the feedback about your room being clean and comfortable, and that our staff were caring and professional. During the Summer months we provide a complimentary shuttle to and from the Shakespeare Festival. If you find yourself back in Ashland this Summer, we would be happy to accommodate you! Sincerely, Chloe Guest Relations

Easy access, good value

18/04/2017 V1555JRsusanh, Corvallis, United States

Easy access for travel on I-5. Nice room, clean, good breakfast. Great location, just a short drive to see plays or lovely walk through park. Rooms are nice, staff super friendly. After a long drive ... more

Owner Response
AshlandWindsor, Guest Relations Manager at BEST WESTERN Windsor Inn, responded to this review
Dear Guest, Thank you for providing such a complimentary review from your stay with us. I am delighted to hear that you found our location conveniently right off of Interstate-5, and it was only a quick drive to see plays downtown, or visit beautiful Lithia Park. I am also happy to hear that you enjoyed your room, and that our staff was super friendly. We look forward to seeing you again soon! Sincerely, Chloe Guest Relations

Wonderful Best Western

17/04/2017 Ellekaysnap, Eugene, Oregon

I enjoyed my stay. Great staff! Comfortable and clean room! Wonderful stay! I arrived late in the evening and the desk clerk was very friendly and helpful. I have already talked to friends and family ... more

Owner Response
AshlandWindsor, Guest Relations Manager at BEST WESTERN Windsor Inn, responded to this review
Dear Guest, Thank you for taking the time to tell us about your wonderful stay! I am happy to hear that your received a warm welcome after your late arrival. We are so glad you enjoyed the comforts of your guest room, and that it was a very clean room. Thank you for telling others about your positive experience here, and we look forward to seeing you on your next trip through Ashland. Sincerely, Chloe Guest Relations