2520 Ashland Street, Ashland, OR 97520-1412
Phone: 541/488-2330   |   Fax: 541/482-1068   |   91 Rooms
Check Out Time: 11:00 AM   |   Check In: 3:00 PM   |   Online Reservations

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 Ashland’s 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.


Hotel Amenities & Services

  • Exercise facilities
  • Wireless internet connection in public areas
  • 100 % smoke-free hotel
  • Complimentary full breakfast, choice of breads, cereal, fruit, hot eggs, hot breakfast meat, other hot items, yogurt, juice, and coffee.
  • Outdoor pool
  • Spa
  • Complimentary breakfast
  • Exercise facility
  • Guest laundry, onsite
  • Ice/vending machines
  • 24-hour front desk
  • Free parking
  • Parking for the physically challenged
  • Conference facilities
  • Fax services
  • Photocopy services
  • Truck/RV parking, limted availability
  • Exterior corridor
  • Free wireless Internet access available in public areas and all guest rooms
  • Air-conditioning
  • Physically challenged services, ADA rooms include a portable shower bench.
  • Hearing impaired services, We have a TTY kit available upon request.
  • Physically challenged facilities
  • Local shuttle, Shuttle to Shakespeare festival runs May through October, must reserve with at least 1 hour notice. Please call front desk for availability and other questions.
  • Outdoor parking, 24 hours
  • Motor coach parking, free
  • Gardens
  • Shuttle to & from Oregon Shakespeare Festival


Take advantage of the savings and fun with this special offer available at the best western windsor inn in Ashland.


Conveniently located, the best western windsor inn in Ashland, Oregon is shown on the map. Detailed driving directions from popular points or nearby cities are listed below. For those with GPS, here you go:

Longitude: 42.185405  /  Latitude: -122.662495


Driving Directions to Hotel


From: I-5 Southbound. Exit # 14 and go east over Interstate 5 and the BEST WESTERN Windsor Inn is ½ mile on right.

From: I-5·Northbound. Exit # 14 and go east, the BEST WESTERN Windsor Inn is ½ mile on right.


We care about the quality of your stay with us. Below are nearby attractions, shopping and restaurants that are popular with our guests. Listed locations are nearby with approximate distance listed where available.

Most Popular Area Attractions

Oregon Shakespeare Festival

Established in 1935, the Oregon Shakespeare Festival takes place in southern Oregon in the city of Ashland. Spanning annually from February to November, OSF is a repertory theatre with a focus on Shakespeare.

The Oregon Shakespeare Festival is hosted on a four-acre campus – or Festival Courtyard – which includes the Angus Bowmer Theatre, Thomas Theatre, and the iconic Elizabethan Theatre.

Southern Oregon University

Southern Oregon University, located in Ashland, began as Ashland Academy in 1872. It became an official state normal school in 1887, but it closed in 1890, due to lack of funding. In 1895, the school reopened and was named Southern Oregon State Normal School. The school was built on its current location, after another closure from 1909 to 1926. Throughout the years and accreditation from the American Association of Teachers Colleges, the school was finally named Southern Oregon University in 1997.

This four-year university is a member of the Council of Public Liberal Arts Colleges and offers bachelor and master degrees from its College of Arts and Sciences, the School of Education and the School of Business. Over 5,000 students attend the main campus, as well as attend classes at the satellite campus in MedfordOregon Health Science University is also located on the main campus. While in Southern Oregon, partake in a guided tour of campus to learn more about this wonderful university. Make the most of your time in Ashland, by checking into one of the local Best Western hotels and enjoy the comfortable accommodations.

More Area Attractions & Services

Distances to Popular Points of Interest

  • 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

Local Area Recreation Opportunities

  • Outdoor pool
  • Spa
  • 0.50 mile(s) from Oak Knoll Golf Course, public golf course
  • 3.00 mile(s) from Emigrant Lake, jet-ski rentals, swimming and water slides
  • 3.00 mile(s) from Lithia Park, over 500 acres of walking trails and ponds
  • 6.60 mile(s) from Emigrant Lake, Park offers camping, swimming, picnicking, rv park, hiking, boating, rock climbing, canoeing and fishing for bass crappie and trout.
  • 15.00 mile(s) from Mount Ashland Ski Resort
  • 46.60 mile(s) from Applegate Lake, Applegate is home to many birds, wildlife, and several extraordinary fisheries; trout & bass being most popular. Trails around the lake lead you on the 17.5 mile shoreline. The lake offers convenient boat launching, day use areas, swimming, RV & tent camping, and a general store.
  • 64.00 mile(s) from Illinois River, The river offers marvelous recreation opportunities, including whitewater that provides plenty of excitement for small rafts and kayaks. The wild section flows through a steep canyon for 29 miles between Briggs & Nancy Creeks, featuring 150 rapids

Nearby Restaurants


Enjoy your stay with us even more by checking out some of the most popular area points of interest and local area events happening in or near Ashland. Chase the links to explore the local region even more.

Local Events Worth Considering:

February 2015

February 20 - November 1, 2015
Ashland Shakespeare Festival

Ashland's famous festival gets underway for the 2015 seasons. Notable productions include Much Ado about Nothing, Guys and Dolls, and Pericles.

August 2015

August 15 - 16, 2015
Wild Rivers Music Festival

Brookings's Azalea Park hosts this two-day music festival.

August 7 - 9, 2015
Pirates of the Pacific Festival

Enjoy this fun-filled pirate adventure show, complete with music, re-enactments, and cannon fire. It is held in Brookings.

September 2015

September 4 - 6, 2015
Slam'n Salmon Ocean Derby

This exciting 3-day event gathers fishermen and friends in salmon-catching contests at Brookings.

September 4 - 6, 2015
Lake County Fair and Round-up

Lakeview's classic rodeo event gets under way, with bull riding, bareback riding, barrel racing, and more.

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