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 Thomas Theatre.
Cottages in Ashland
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Oct 9 - Oct 11Top 5 hotels in Ashland at a glance
- Paschal Winery — 4.5-star hotel in Talent. Guest rating: 9.8/10 — Exceptional.
- Forest Cabin by Crater Lake & Klamath Falls — 3-star hotel in Klamath Falls.
Cottages in Ashland
$155
$439 total
includes taxes & fees
Aug 18 - Aug 19
Forest Cabin by Crater Lake & Klamath Falls
Forest Cabin by Crater Lake & Klamath FallsKlamath Falls
$109
$213 total
includes taxes & fees
Aug 16 - Aug 17
Top neighborhoods in Ashland
- Historic Railroad District
- Skidmore Academy Historic District
- Historic Downtown District
- Siskiyou-Hargadine Historic District
Photo by Inna Blair
Historic Railroad District
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.
Photo by Shannon Willitts
Skidmore Academy Historic District
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.
Photo by Shannon Willitts
Photo by Patrick Glassford
Photo by Shannon Willitts
Photo by Shannon Willitts
Historic Downtown District
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
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.
Top landmarks in Ashland
Photo by Patrick Glassford
Oregon Shakespeare Festival
9.2/10 (620 reviews)
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, Thomas Theatre, Allen Elizabethan Theatre, and Angus Bowmer Theatre are all a short walk away.
Photo by Shannon Willitts
Lithia Park
9.6/10 (1,250 reviews)
Lithia Park is 0.5 mi (0.9 km) from central Ashland, why not stop by during your stay. It's also full of great shops and restaurants, so you can spend the afternoon having a wander. Want to stretch your legs some more? Head to North Mountain Park, located nearby.
Mount Ashland Ski Area
8.6/10 (228 reviews)
Skiers and snowboarders might want to test out the slopes at Mount Ashland Ski Area, a skiing spot located 7.8 mi (12.5 km) from central Ashland.
Howard Prairie Lake
8.4/10 (33 reviews)
Howard Prairie Lake is 16.1 mi (26 km) from central Ashland, why not stop by during your stay.
Emigrant Lake
8.4/10 (70 reviews)
Emigrant Lake is 6.3 mi (10.2 km) from central Ashland, why not stop by during your stay. It's also full of great shops and restaurants, so you can spend the afternoon having a wander.
Allen Elizabethan Theatre
9.4/10 (131 reviews)
If you want to see a show while you're in town, try and grab some tickets at Allen Elizabethan Theatre in Historic Downtown District. If you enjoy the show and want to see another, Thomas Theatre, Oregon Shakespeare Festival, and Angus Bowmer Theatre are all a short walk away.
Oregon Cabaret Theatre
9.0/10 (144 reviews)
If you want to see a show while you're in town, try and grab some tickets at Oregon Cabaret Theatre in Historic Downtown District. It's also full of great shops and restaurants, so you can spend the afternoon having a wander. If you enjoy the show and want to see another, Oregon Shakespeare Festival, Thomas Theatre, and Allen Elizabethan Theatre are all a short walk away.
Thomas Theatre
9.4/10 (144 reviews)
If you want to see a show while you're in town, try and grab some tickets at Thomas Theatre in Historic Downtown District. If you enjoy the show and want to see another, Allen Elizabethan Theatre, Oregon Shakespeare Festival, and Angus Bowmer Theatre are all a short walk away.
Learn more about Ashland
Between Shakespeare and the sublime, this artsy enclave captivates with its cultural punch far beyond its size. The Oregon Shakespeare Festival transforms three theaters into worlds of drama nearly year-round, drawing theater lovers who linger after standing ovations. Main Street's independent boutiques and farm-to-table restaurants showcase local creativity without pretension. Lithia Park unfolds like a living painting—creek-side paths wind through 93 acres where picnickers claim spots beneath ancient trees. Southern Oregon University adds youthful energy to this intellectual haven. After hiking nearby trails, soak tired muscles in Lithia Plaza's mineral-rich fountains (warning: the water tastes terrible). For a perfect day, catch a matinee, browse gallery-quality crafts, then toast the sunset with local wines.
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