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!


Hotel Amenities & Services

  • 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

  • 3.00 mile(s) from Oregon Shakespeare Festival, largest rotating repertory theatre
  • 3.00 mile(s) from Downtown Ashland
  • 3.00 mile(s) from Oregon Cabaret Theatre, musical theatre and dinner
  • 3.00 mile(s) from Hanson Howard Gallery, fine-art gallery
  • 14.00 mile(s) from Harry & David Tours, Come see how America's favorite treats are made--and taste a few yourself!
  • 15.10 mile(s) from Caterian Theatre, Medford's state-of-the-art community performing arts center.
  • 19.50 mile(s) from Britt Festival, Presents dozens of summer concerts, featuring world-class artists in classical music, jazz, blues, folk, bluegrass, world, pop, and country music.
  • 19.80 mile(s) from Rogue Creamery, Step inside the unassuming cinderblock creamery to discover an assortment of some of the best hand-milled cheddar cheese in the world. There are delicacies to delight every palette. The Rogue Creamery is home of the Rogue River Blue, the finest blue cheese in the world.
  • 20.00 mile(s) from Jacksonville Oregon, historic city with museums
  • 30.00 mile(s) from Table Rock, Once a sanctuary for Takelma Indians, today these cliff-edged mesas near Medford are a haven for hikers and endangered wildfowers.
  • 45.00 mile(s) from Hellgate Jetboat Excursion, tours down Rogue River
  • 94.00 mile(s) from Oregon Caves National Monument, Nestled deep inside the Siskiyou Mountains, the caves formed as rainwater from the ancient forest above dissolved the surrounding marble and created one of the world's few marble caves. The highly complex geology found on the Monument contributes to the unusual and rare plants and animals found nowhere else but here. Experience the extensively decorated and adventurous "Marble Halls of Oregon."
  • 97.10 mile(s) from Crater Lake National Park, One of the Natural Wonders of the World, Crater Lake is like no place else on earth.
  • 110 mile(s) from Wildlife Safari, The Wildlife Safari is a fun-filled family destination where you can view over 500 animals in their natural habitat, roaming free as they do in the wild! Visitors to the park drive through a 4.5 mile trek to see animals from Africa, Asia, and the Americas.
  • 15.00 mile(s) from Rogue Valley Mall, indoor shopping mall

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

  • Choose from a wide selection of restaurants near this Ashland, Oregon hotel.
  • Adjacent to Oak Tree Northwest, American, and Mexican cuisine
  • 0.50 mile(s) from Wild Goose, American
  • 1.00 mile(s) from Jade Dragon, Chinese
  • 1.00 mile(s) from Apple Cellar, American
  • 1.00 mile(s) from Pizza Hut,
  • 1.00 mile(s) from McDonald's
  • 2.00 mile(s) from Omar's, steak and seafood


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:

January 2014

Second Saturday of Each Month
Free Kids Day

Hit up the Crater Rock Museum and let the kids play in the dirt, but this time it's for education purposes! They will learn about fossils, geodes, and even dinosaurs. The museum opens at 10 a.m.

March 2014

February 15 - May 11, 2014
Prehistoric Predators

Travel back in time and walk among the dinosaurs at the ScienceWorks Hands-on Museum in Ashland. These impressive robots can track you as you pass through their environment. Times vary per day.

March 29 - April 27, 2014
Far Out! Southern Oregon in the 1960s

Stop by and see the array of photographs and other artifacts that tell stories and illustrate what life would have been like back in the 1960s. Times vary per day.

April 2014

April 26, 2014
Ahh Shucks! Oyster Feed Head on down to the Oregon Institute of Marine Biology for live music and fresh Oysters, or hotdogs if you prefer. It all starts at noon.

May 2014

May 3, 2014
Celtic Cultural Festival

A day long event full of Celtic music, dance, songs, and stories at the Southwestern Oregon Community College.

June 2014

June 1, 2014
Oregon Gran Fondo Downtown Cottage Grove fills with hundreds of cyclists as they ride for 117, 71, or 31 miles in this kick off event for the Oregon Triple Crown Series. Start times vary based on length.

July 2014

July 26, 2014
Rolf Prima Tri at the Grove This USATriathlon sanctioned race takes place at the Cottage Grove Lake. Start times vary for Olympic and Sprint distances.

September 2014

September 20, 2014
Cycle the Lakes Join in on this fun and active event starting in Bohemia Park with three different lengths to choose, 32, 67, or 102 miles. Starts times and routes vary based upon length.
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