The Best Hotels to Book in Ashland, Oregon

Experience Oregon's spectacular landscape for yourself with a stay in Ashland
Experience Oregon's spectacular landscape for yourself with a stay in Ashland | Courtesy of Ashland Springs Hotel / Expedia
Photo of Julia Sayers Gokhale
28 October 2021

It might not have the world-renown of its bigger sibling cities, but small Ashland – in the south of Oregon – is a cultural gem. People come from all over for its famous Shakespeare Festival, which isn’t a one-off event, but rather a series of plays that run from February to October. Year-round recreation draws visitors to Ashland for hiking in the Siskiyou and Cascade mountain ranges, skiing at Mt Ashland Ski Area or wandering the peaceful Lithia Park. Discover this undercover star yourself with a stay in one of these unique hotels, bookable on Culture Trip.

Ashland Springs Hotel, for art deco details

4.5/5 (928 Reviews)
Ashland Springs Hotel
Courtesy of Ashland Springs Hotel / Expedia
Price Drop
Now from $112 per night
Wherever you stand in Ashland, there’s one building that towers over everything else – the sugar cube-white, art deco building that houses the Ashland Springs Hotel has been a local landmark since 1925. It originally opened as the Lithia Springs Hotel, but underwent a massive restoration in 2000 and reopened as Ashland Springs Hotel. Inside, European opulence abounds with crystal chandeliers, grand columns and a two-story lobby. Pastel-colored guest rooms feature arched windows framing views of the surrounding mountain ranges.
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Best Western Windsor Inn, for chalet-style chic

4.4/5 (963 Reviews)
Best Western Windsor Inn
Courtesy of Best Western Windsor Inn / Expedia
Price Drop
Now from $103 per night
With its red and green exposed exterior beams, steeply pitched roofs and ornately balustraded balconies, this Best Western is less classic roadside motel, and more Swiss mountain lodge. Cozy guest quarters are situated around an outdoor pool and year-round hot tub, several restaurants are within walking distance of the hotel, and downtown Ashland is just a 10-minute drive. The hotel also recently added electric vehicle charging to the site to accommodate those on an ecofriendly road trip through Oregon.
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Lithia Springs Resort, for a spa-themed stay

4.7/5 (949 Reviews)
Lithia Springs Resort
Courtesy of Lithia Springs Resort / Expedia
Price Drop
Now from $109 per night
Take a deep breath and relax at one of the most peaceful hotels in Ashland. Lithia Springs Resort encourages rejuvenation via the freshwater springs found deep beneath the resort. Rich in sulphur and other rejuvenating minerals, the waters’ restorative benefits can be enjoyed in your own soaking tub, mineral shower or at the spa. Peaceful nooks can be found throughout the grounds of the resort, including a saline swimming pool, koi pond and romantic gazebo. Taste Southern Oregon wines from the Applegate Valley at the on-site Wine Garden.
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Ashland Hills Hotel & Suites, for old-school cool

4.5/5 (1479 Reviews)
Ashland Hills Hotel and Suites
Courtesy of Ashland Hills Hotel and Suites / Expedia
Price Drop
Now from $115 per night
At the base of the Siskiyou Mountains, many of the retro-chic rooms and suites of this recently revamped hotel have balconies with expansive mountain views. Snag a spot on a bright orange lounger by the pool and order poolside snacks from Luna Cafe. When you’re ready to venture out, grab a cruiser bike from the hotel and zip around to nearby restaurants and attractions. For a unique souvenir, the hotel offers guests the option to make an Oregon gift box from local wines and cheeses.
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Plaza Inn & Suites at Ashland Creek, for a Shakespearean showstopper

4.5/5 (1161 Reviews)
Plaza Inn and Suites at Ashland Creek
Courtesy of Plaza Inn and Suites at Ashland Creek / Expedia
Price Drop
Now from $154 per night
In town for the Shakespeare Festival? Double down on the drama with a stay at this Shakespearean-themed boutique, within walking distance of Ashland’s theater district, as well as other attractions like Lithia Park and more than 70 downtown restaurants. After a night on the town, retreat to the hotel and enjoy an evening snack— the hotel offers nightly complimentary cookies and PB&J sandwiches.
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  • Comfort Inn & Suites, for college convenience

    4.3/5 (969 Reviews)
    Comfort Inn and Suites Ashland
    Courtesy of Comfort Inn and Suites Ashland / Expedia
    Price Drop
    Now from $91 per night
    A grand portico marks your arrival to the Ashland Comfort Inn & Suites. The hotel is located near Southern Oregon University, making it a popular stay during graduations and other university events. Even if you don’t have a student at the college, the hotel encourages taking a walk through the tree-lined campus. Spacious suites at Comfort Inn are great for families. The hotel is located less than a 10-minute drive to downtown Ashland.
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    Arden Forest Inn, for woodland wonderment

    4.9/5 (19 Reviews)
    Arden Forest Inn
    Courtesy of Arden Forest Inn / Expedia
    Price Drop
    Now from $122 per night
    The Arden Forest Inn is an enchanting and magical stay unlike any other hotel in Ashland. The bed and breakfast features five suites, all with their own private paths. For more than 30 years, the owners have welcomed guests to their forest abode and regaled them with their extensive knowledge of theater and Shakespeare. After enjoying a home-made breakfast spread, wander the inn’s private gardens and discover peaceful walkways, sculptures, gazebos and a heated pool.
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    Country Willows Inn, for farm-themed fun

    5/5 (84 Reviews)
    Country Willows Inn
    Courtesy of Country Willows Inn / Expedia
    Price Drop
    Now from $164 per night
    Farmstead chic describes Country Willows Inn perfectly. Sit in an Adirondack chair under a willow tree or hike beside babbling brooks at this bed and breakfast, located on 5 acres (2ha) of land. Rooms at the inn, as well as a private cottage, were inspired by European country houses. Barn suites take their design influence from Southern Oregon and the Northwest. On summer afternoons, the inn hosts live music in their gardens.
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