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Hotels in Ashland
3 Hotels
Best Western Windsor Inn
2520 Ashland St

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. 

Ashland Hills Hotel & Suites
2525 Ashland Street

The Ashland Hills Hotel and Suites is a 100-room, mid-range property on the outskirts of Ashland, with lots of perks not usually found in hotels at this price point. Moderately retro-style rooms and suites have flat-screen TVs, fridges, and coffeemakers, and some have private balconies. Some of the suites have pull-out sofa beds, but the hotel charges an extra fee for their use. Breakfast is included in room rates and Wi-Fi and parking are free. There's also a pair of tennis courts, an outdoor pool, a hot tub, and a tiny, worn fitness center, but no restaurant for lunch and dinner. Visitors may want to check out the similarly priced Best Western Windsor Inn, which also offers a free breakfast and has nicer fitness facilities.  

Ashland Springs Hotel
212 E Main St

The 70-room Ashland Springs Hotel is an upper-middle-range, historic boutique property with lots of on-site features. The rates are surprisingly low, especially given its convenient city center location right by the Oregon Shakespeare Festival venue. Rooms have European-style decor, air-conditioning, and flat-screen TVs with cable. There's also a great on-site restaurant serving a menu of locally sourced Northwest cuisine, and breakfast, afternoon tea, and cookies are included in room rates. Wi-Fi and parking are also free, and there are five elegant event spaces for meetings and weddings. However, there's no fitness center or pool on-site; guests looking for a more active vacation -- or those visiting in the summer with kids in tow -- may prefer the Ashland Hills Hotel & Suites, a sister property with a pool, a tiny fitness room, and a couple of tennis courts.