Pros

  • A short drive to Southern Oregon University and downtown Ashland
  • Simple rooms and suites with Keurig coffeemakers and mini-fridges
  • Suites with kitchenettes or whirlpool tubs available
  • Large outdoor swimming pool with adjacent whirlpool hot tub
  • Sunny fitness center with cardio and weight machines
  • Shuttle to Oregon Shakespeare Festival May through October
  • Free Wi-Fi throughout, continental breakfast, and on-site parking
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Cons

  • Not much within walking distance
  • No on-site restaurant for lunch and dinner
  • Generic room decor lacks charm
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Bottom Line

The 91-room Best Western Windsor Inn is a mid-range chain hotel on the outskirts of Ashland. Rooms have generic chain decor, but come with nice perks such as Keurig coffeemakers, while some suites have whirlpool tubs for two. Amenities include a large outdoor pool that's open in warmer months, a fitness room, and a free hot and cold continental breakfast. While the hotel offers a shuttle to the Oregon Shakespeare Festival, guests wanting to walk around town might prefer to stay somewhere more central, such as the Ashland Springs Hotel. 

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Amenities

  • Fitness Center
  • Internet
  • Jacuzzi
  • Pets Allowed
  • Pool

Oyster Hotel Review

Best Western Windsor Inn

Scene

Mid-range chain hotel with vaguely Bavarian decor scheme

The exterior of this Best Western evokes a Bavarian lodge, with a large triangular facade decked out in multicolored trim. Even the lobby feels folksy, thanks largely to low ceilings and an all-wood reception desk, though the decor is likely a nod to the Oregon Shakespeare Festival, Ashland's signature attraction. Most of the grounds are occupied by a large parking lot, though there's also an outdoor swimming pool and a bit of greenery surrounding the property. The breakfast room is more typical of a value chain hotel, with dark-brown carpeting and matching chairs along with big windows that let in plenty of light and a flat-screen TV in the corner. Guests here are mostly tourists and road-trippers passing through, and it's a good choice for families with children as well as business travelers. 

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Location

Right off Interstate-5, near the municipal airport and Southern Oregon University

The Best Western Windsor Inn is located just off I-5 (exit 14), a 20-minute drive north of the Oregon/California border. It's located right by the Ashland Municipal Airport, and it's a five-minute drive to Southern Oregon University and less than a 10-minute drive into the center of town. The hot springs at Jackson Wellspring are about an eight-minute drive from the hotel. The closest commercial airport is in Medford, a 20-minute drive away. Crater Lake National Park is about an hour and a half away by car. It's a three-hour drive to Eugene and a four-and-a-half-hour drive to Portland, Oregon. 

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Rooms

Rooms and suites with generic decor, some with whirlpool hot tubs or well-stocked kitchenettes

The hotel offers a variety of room types, all of which share a generic decor scheme, unsurprising for a chain hotel. Rooms have patterned carpets, cherry-colored wooden desks and dressers, mini-fridges, and flat-screen TVs. Beds have white linens and blue-scale striped cushions, runners, and padded headboards, while framed photographs of Oregon mountains add a little warmth to the plain cream-colored walls. Bathrooms have shower/tub combos and separate vanity areas with double basins and small hairdryers. Spacious suites have extras such as kitchenettes or whirlpool hot tubs. Those with kitchenettes offer four-burner stoves, a huge selection of cookware and utensils, ovens, microwaves, and double basins. ADA Accessible units are also available.

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Features

Free continental breakfast, shuttle to Shakespeare Festival, fitness room, pool, and ample parking

Although there's no proper restaurant on-site, the hotel does offer a free breakfast with standard continental fare plus eggs and meats. There's also a sunny fitness center in a carpeted room with a treadmill, an elliptical, and a weight-training station. The outdoor swimming pool is large and gets a lot of sunlight, and there's also a large whirlpool hot tub. The hotel has a business center with a PC computer and a printer, and Wi-Fi is free throughout the property. Free parking is available on-site, with spaces for trucks and RVs. The hotel also offers a free shuttle to the Oregon Shakespeare Festival May through October. 

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Oyster Hotel Review

Best Western Windsor Inn

Scene

Mid-range chain hotel with vaguely Bavarian decor scheme

The exterior of this Best Western evokes a Bavarian lodge, with a large triangular facade decked out in multicolored trim. Even the lobby feels folksy, thanks largely to low ceilings and an all-wood reception desk, though the decor is likely a nod to the Oregon Shakespeare Festival, Ashland's signature attraction. Most of the grounds are occupied by a large parking lot, though there's also an outdoor swimming pool and a bit of greenery surrounding the property. The breakfast room is more typical of a value chain hotel, with dark-brown carpeting and matching chairs along with big windows that let in plenty of light and a flat-screen TV in the corner. Guests here are mostly tourists and road-trippers passing through, and it's a good choice for families with children as well as business travelers. 

See More Scene

Location

Right off Interstate-5, near the municipal airport and Southern Oregon University

The Best Western Windsor Inn is located just off I-5 (exit 14), a 20-minute drive north of the Oregon/California border. It's located right by the Ashland Municipal Airport, and it's a five-minute drive to Southern Oregon University and less than a 10-minute drive into the center of town. The hot springs at Jackson Wellspring are about an eight-minute drive from the hotel. The closest commercial airport is in Medford, a 20-minute drive away. Crater Lake National Park is about an hour and a half away by car. It's a three-hour drive to Eugene and a four-and-a-half-hour drive to Portland, Oregon. 

See More Location

Rooms

Rooms and suites with generic decor, some with whirlpool hot tubs or well-stocked kitchenettes

The hotel offers a variety of room types, all of which share a generic decor scheme, unsurprising for a chain hotel. Rooms have patterned carpets, cherry-colored wooden desks and dressers, mini-fridges, and flat-screen TVs. Beds have white linens and blue-scale striped cushions, runners, and padded headboards, while framed photographs of Oregon mountains add a little warmth to the plain cream-colored walls. Bathrooms have shower/tub combos and separate vanity areas with double basins and small hairdryers. Spacious suites have extras such as kitchenettes or whirlpool hot tubs. Those with kitchenettes offer four-burner stoves, a huge selection of cookware and utensils, ovens, microwaves, and double basins. ADA Accessible units are also available.

See More Rooms

Features

Free continental breakfast, shuttle to Shakespeare Festival, fitness room, pool, and ample parking

Although there's no proper restaurant on-site, the hotel does offer a free breakfast with standard continental fare plus eggs and meats. There's also a sunny fitness center in a carpeted room with a treadmill, an elliptical, and a weight-training station. The outdoor swimming pool is large and gets a lot of sunlight, and there's also a large whirlpool hot tub. The hotel has a business center with a PC computer and a printer, and Wi-Fi is free throughout the property. Free parking is available on-site, with spaces for trucks and RVs. The hotel also offers a free shuttle to the Oregon Shakespeare Festival May through October. 

See More Features

Best Rates

Amenities

  • Balcony / Terrace / Patio

  • Cabanas

  • Cable

  • Fitness Center

  • Free Breakfast

  • Full Kitchen

  • Internet

  • Jacuzzi

  • Kids Allowed

  • Meeting / Conference Rooms

  • Pets Allowed

  • Pool

  • Poolside Drink Service

  • Rental Car Service Desk Onsite

  • Separate Bedroom / Living Room Space

  • Swim-Up Bar

Disclaimer: This content was accurate at the time the hotel was reviewed. Please check our partner sites when booking to verify that details are still correct.