Top Guest Houses in Ashland, OR

A stone bridge over a calm stream with autumn leaves.

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Recommended hotels in Ashland

A grand lobby with a high ceiling, large windows, and a central staircase.

1. Ashland Springs Hotel

Historic Downtown District

$120 total

includes taxes & fees

Dec 13 - Dec 14

An indoor swimming pool with clear water, tiled edges, and a blue mosaic border. There are lounge chairs and potted plants near the windows.

2. Stratford Inn

Siskiyou-Hargadine Historic District

$84 total

includes taxes & fees

Nov 15 - Nov 16

A sign for Prospero's Flagship Inn with a star emblem and a pedestrian crossing sign nearby.

3. Prospero's Flagship Inn

Ashland

$66 total

includes taxes & fees

Nov 16 - Nov 17

A well-lit room with a sofa, chairs, and a coffee table. There are bookshelves filled with books and decorative items.

4. Lithia Springs Resort

Ashland

$115 total

includes taxes & fees

Nov 16 - Nov 17

A Holiday Inn Express hotel with a two-story structure, a parking lot, and a landscaped area with shrubs and a tall tree.

5. Holiday Inn Express & Suites Ashland by IHG

Ashland

$103 total

includes taxes & fees

Dec 10 - Dec 11

A spacious living room with hardwood flooring, a large window with a view, and a peace sign decoration.

6. Ashland Hills Hotel & Suites

Ashland

$128 total

includes taxes & fees

Nov 23 - Nov 24

A hotel entrance with outdoor seating, potted plants, and a well-lit facade.

7. Comfort Inn & Suites Ashland

Ashland

$96 total

includes taxes & fees

Dec 13 - Dec 14

8. Callahan's Mountain Lodge

Ashland

$109 total

includes taxes & fees

Dec 11 - Dec 12

A spacious lobby with a reception desk, seating area, and large windows.

9. The Bard's Inn, BW Signature Collection by Best Western

Historic Downtown District

$93 total

includes taxes & fees

Dec 6 - Dec 7

An outdoor dining area with a table set for two, surrounded by chairs, a red umbrella, and a stone water feature.

10. Plaza Inn & Suites at Ashland Creek

Ashland

$129 total

includes taxes & fees

Nov 15 - Nov 16

11. Best Western Windsor Inn

Ashland

$126 total

includes taxes & fees

Nov 18 - Nov 19

A swimming pool with a clear view of the poolside area, including lounge chairs and a covered seating area.

12. Timbers INN and Suites

Ashland

$89 total

includes taxes & fees

Nov 15 - Nov 16

A two-story building with a wooden facade, large windows, and a front porch with chairs.

13. The Peerless Hotel by WanderLodges

Historic Railroad District

$157 total

includes taxes & fees

Nov 23 - Nov 24

A large, two-story house with a wrap-around porch and a steeply pitched roof.

14. Winchester Inn

Historic Downtown District

$178 total

includes taxes & fees

Nov 15 - Nov 16

A balcony with a view of a residential area, a black pickup truck, and a white RV parked in the foreground.

15. Ashland Commons Hostel

Ashland

$55 total

includes taxes & fees

Nov 15 - Nov 16

A hotel room with a desk, laptop, two beds, and a round mirror.

16. Ashland Motel - Oregon

Ashland

$90 total

includes taxes & fees

Nov 15 - Nov 16

A dining area with a wooden table and chairs, a potted plant, and a window with blinds.

17. Cedarwood Inn of Ashland

Ashland

$84 total

includes taxes & fees

Nov 13 - Nov 14

A Victorian-style building with ornate architectural details, large windows, and a red door.

18. McCall House Boutique Inn

Historic Downtown District

$195 total

includes taxes & fees

Nov 13 - Nov 14

A backyard with a swimming pool, patio furniture, a small pond, and a wooden cabin.

19. Country Willows Inn and Estate

Ashland

$214 total

includes taxes & fees

Nov 13 - Nov 14

A hotel room with a bed, bedside tables, a desk, a chair, a dresser, and a painting on the wall.

20. Baymont by Wyndham Ashland OR

Ashland

$100 total

includes taxes & fees

Nov 13 - Nov 14

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Top neighborhoods in Ashland

A rusted metal bridge in a forested area.

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.

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A town with buildings and trees in autumn colors, surrounded by mountains.

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.

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A paved pedestrian area with trees, a white building with a green awning, and a dog walking.

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.

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A tree-lined street with a mountain backdrop.

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.

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Top landmarks in Ashland

A statue of a person in a brown outfit with a hat and sunglasses, holding a pipe and a book, standing on a pedestal in a park with green bushes and trees.

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, Allen Elizabethan Theatre, Oregon Cabaret Theatre, and Thomas Theatre are all a short walk away.

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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, Allen Elizabethan Theatre, and Thomas Theatre are all a short walk away.

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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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About the destination

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 Angus Bowmer Theatre.