Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Ashland's Historic Railroad District captures Oregon's cultural heart with Victorian charm and artistic soul. Tree-lined streets connect 19th-century buildings where theater and history share the spotlight. The Shakespeare Festival brings brick walkways alive with theatrical buzz. Art galleries in former rail buildings showcase local talent amid cobblestone plazas adorned with bronze sculptures.
Farm-to-table restaurants serve Pacific Northwest cuisine in converted Victorian spaces, perfect for dining with regional wines. Boutique inns and historic bed & breakfasts offer intimate stays with period furnishings and modern comforts. The pedestrian-friendly design makes exploring a joy, with attractions within an easy stroll through this walkable cultural haven.
Step back in time as you stroll the tree-lined streets of Skidmore Academy Historic District, where Victorian architecture meets theatrical flair. Ornate 19th-century buildings, including the original Skidmore Academy, tell the story of Ashland's rich heritage. The district sits conveniently close to Oregon Shakespeare Festival venues, where world-class performances bring creative energy to this peaceful neighborhood.
Intimate cafes and bistros cater to theater-goers with pre-show dining featuring seasonal Pacific Northwest ingredients. Charming bed-and-breakfasts in converted Victorian homes offer cozy accommodations with period furnishings. The walkable streets connect easily to downtown Ashland, making exploration a breeze without the need for public transportation.
Historic Downtown District brings Shakespeare to life in Ashland's charming center. The renowned Oregon Shakespeare Festival anchors the neighborhood with Tudor-style theaters surrounded by Victorian storefronts. Lithia Park offers a peaceful escape with bubbling mineral springs, while art galleries and boutiques fill historic buildings beneath colorful awnings.
Farm-to-table restaurants showcase local Oregon wines, though reservations are essential during festival season. Accommodation options include Victorian bed & breakfasts and boutique inns within this highly walkable neighborhood. Most attractions sit within a three-block radius, making cars unnecessary for exploring this theatrical paradise.
Siskiyou-Hargadine Historic District offers a step back in time with pristine Victorian and Craftsman homes lining tree-canopied streets. Take a leisurely stroll through architectural history while enjoying the peaceful vibe just steps from Ashland's cultural buzz. The Oregon Shakespeare Festival and Oregon Cabaret Theatre are an easy walk away, making this neighborhood perfect for theater enthusiasts.
Accommodations range from charming bed & breakfasts in restored Victorians to boutique inns with period furnishings. Downtown Ashland's diverse restaurants and artisan shops are just a 5-10 minute walk away. The neighborhood's uncrowded sidewalks and proximity to Lithia Park create an ideal base for exploring Ashland without a car.
If you want to see a show while you're in town, try and grab some tickets at Oregon Shakespeare Festival in Historic Downtown District. If you enjoy the show and want to see another, Allen Elizabethan Theatre, Oregon Cabaret Theatre, and Thomas Theatre are all a short walk away.
Explore the great outdoors at Lithia Park, a lovely green space in Ashland. Discover the top-notch restaurants and entertainment choices in this family-friendly area.
You can make plans for a show at Oregon Cabaret Theatre during your trip to Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.
Commune with nature and explore the great outdoors at Howard Prairie Lake during your travels in Ashland. While in this family-friendly area, you can savor the top-notch restaurants.
Immerse yourself in world-class theater at the Oregon Shakespeare Festival, running nearly year-round. Explore charming boutiques and farm-to-table eateries along Main Street before hiking in nearby Lithia Park.
"The hotel was very clean and conveniently located within walking distance to the theater and downtown. The staff was friendly, and we really enjoyed our stay. We would definitely stay here again and highly recommend it."
"Close walk to the plays and Main Street dining! Beautifully restored hotel with all the amenities. Loved our stay, will definitely choose The Peerless next time in Ashland!"
"I loved that the working people were very kind to my older Vizsla medical Service dog. I have owned her for 11years—she is now 12. She has been my first & only service dog, and the best! The man who tried to kill me on September 28, 2012 is now dead…so my life in California has returned where I grew up—Redding! 瑩♥️"
If you need the flexibility to change your plans to Ashland, most properties provide refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where should I stay in Ashland if I want a cheap accommodation?
Where can I stay in Ashland if I want a vacation rental instead of a traditional hotel?
If you're looking for a good alternative to a hotel, look over our selection of 131 vacation homes. You can also consider one of the 49 apartments or 61 cottages.
What will the weather in Ashland be like during my trip?
The warmest months in Ashland are usually August and July with an average temp of 65°F. December and January are the chilliest months when the average temp is 37°F. The rainiest months are December and March.
Why should I book my Ashland hotel with Hotels.com?
There are plenty of reasons to book your Ashland travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.
Find out more about Ashland
Find out more about Ashland
Visitors to Ashland like this welcoming city's gardens, entertainment, restaurants, and festivals. Activities like hiking give you a chance to enjoy the outdoors while you're in town. Nature lovers can visit Lithia Park and Emigrant Lake. There's plenty more to see, including sights like Allen Elizabethan Theatre and Oregon Shakespeare Festival.
