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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 1127 traveller reviews
Rating: 5 651
Rating: 4 352
Rating: 3 79
Rating: 2 27
Rating: 1 19

Water was warm for showers not hot disappointed

24/06/2018 leesgrl, sparks nv

We were there for a camp for our kid Only complaint is showers were warm only no hot water for shower morning or night otherwise it’s A ok place to stay didn’t have many choices to stay in Ashland . ... more


Delightful stay & perfect location

23/06/2018 Margaret M,

Staff were wonderful, sauna / pool were a bonus after early morning hike and an afternoon stroll through Lithia park Thank you for the beautiful linens and towels which been lost amongst most lodging ... more


Wonderful Every Time

22/06/2018 Benson S,

I am in the Rogue Valley once a month and love to stay here, It's affordable, the rooms are spacious and very quiet and the beds are comfortable. I have a dog and there is lots of room for walking wit... more

Owner Response
AshlandWindsor, Guest Relations Manager at Best Western Windsor Inn, responded to this review
Thank you for staying with us, Benson! We're delighted to hear that you have had consistently wonderful experiences with us. We love having guests' pets come along for the visit! We hope you can return again very soon.

Simple Accommodations

17/06/2018 Nancy S, South Berwick, Maine

Arrived with my sister for a graduation! Stayed one night, the next two nights had two adjoining rooms with additional family members. The buffet breakfast was great with a large variety of items. My ... more

Owner Response
AshlandWindsor, Guest Relations Manager at Best Western Windsor Inn, responded to this review
Hi Nancy, thank you for staying with us and sharing your experience. We apologize for the confusion and miscommunication, as well as the inconvenience this caused your party. We are very sorry to hear that this experience has tarnished your family's perception of our hotel. We thank you for your feedback. We will share your comments with our team as we continuously strive to improve. We hope you will visit us again in the future.

Ashland for visiting relatives

02/06/2018 skb3840SpringLake_MI, Spring Lake, MI

Really well maintained with large rooms. Shower and toilet separate room from wash basins (2). Very good breakfast buffet with the usual offerings and kept well stocked and clean. Easy access off I5 o... more

Owner Response
AshlandWindsor, Guest Relations Manager at Best Western Windsor Inn, responded to this review
Thank you for staying with us and sharing your experience! We're delighted to hear that you had a wonderful experience while visiting your family here in Ashland. We hope you'll be able to return again soon!