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, Seasonal shuttle to & from the Oregon Shakespeare Festival. Must reserve with at least one hour notice. Please call front desk for availability and other questions.
  • Outdoor parking, 24 hours
  • Motor coach parking, free
  • Gardens
  • Seasonal shuttle to & from Oregon Shakespeare Festival. Inquire with front desk for availability.


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

OC&E Woods Line State Trail

Stretched across 105 miles of central Oregon landscape, the OC&E Woods Line State Trail is a recreational trail, reaching from Klamath Falls to the Thompson Reservoir. The trail was established in 1992 on the old lines of the Oregon, California and Eastern Railroads.

Approximately eight miles of the trail is paved making an ideal surface for skating, jogging, bicycling and running. Many visitors enjoy riding on horseback, mountain biking and hiking through the Winema National Forest, or fishing in the Sprague River.

Oregon Shakespeare Festival

Established in 1935, the Oregon Shakespeare Festival takes place in southern Oregon in the city of Ashland. Held 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

Founded in 1872, Southern Oregon University is a public, liberal arts college set in the rural college town of Ashland. Enrolling roughly 6,200 students, the school houses the College of Arts and Sciences, School of Business, and School of Education.

In addition to serving as the southern Oregon satellite campus for the Oregon Health and Science University, SOU offers a satellite campus of its own in downtown Medford. Students and visitors enjoy cheering on the Southern Oregon Raiders as they compete in the Cascade Collegiate Conference.

Upper Klamath Lake

Upper Klamath Lake

Upper Klamath Lake

The largest lake in the state, Upper Klamath Lake is set in southern Oregon, between Klamath Falls and Fort Klamath.

At 30 miles long and eight miles wide, the lake remains a vital water source for irrigation in the upper Klamath Basin.

Upper Klamath Lake is monitored by the U.S. Fish and Wildlife Service in order to protect the fish populations living in the lake.

Visit this incredible lake for an wonderful day of aquatic recreation, viewing sites like the Link River Dam, Wocus Bay, and the shores of the Winema National Forest.

More Area Attractions & Services

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:

December 2015

December 4-6, 2015
2015 Crescent City Annual Holiday Bazaar

A great place to get some holiday shopping done while visiting Brookings. The market will be held at the Del Norte County Fairgrounds – technically in Crescent City – opening at 5 p.m., 10 a.m., and noon, respectively.

January 2016

January 2, 2016
2015 Free Tours of the Historic Holly Theatre

On select Saturdays, Medford visitors are invited to take a free tour of the historic Holly Theatre, the largest remaining grand movie palace in the city. The tours begin at 11 a.m.

January 2016

First Friday's Each Month
2015 Ashland's First Friday Art Walk

Visit the Historical Downtown and Railroad Districts in Ashland and take in the culture on the first Friday of each month this year. Music, food, art, and more are sprinkled throughout the city. The even begins at 5 p.m.

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