Top B&B in Ashland, OR

A stone bridge over a calm stream with autumn leaves.

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B&B in Ashland

A resort with a covered walkway, potted plants, and a statue.

A well-maintained garden with a paved walkway, surrounded by lush greenery and trees.

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

A bar area with a marble countertop, wine bottles, and glasses. There are hanging pendant lights and a 'No Minors' sign.

1. Lithia Springs Resort

Ashland

$94

$115 total

includes taxes & fees

Nov 16 - Nov 17

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

A room with a bay window, two upholstered chairs, a round ottoman, and a small wooden table.

A patio area with string lights, potted plants, and a stone pathway.

A spacious living room with a large sofa, a dining area with a table and chairs, and a chandelier.

2. McCall House Boutique Inn

Historic Downtown District

$208

$232 total

includes taxes & fees

Nov 4 - Nov 5

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

A rustic wooden barn with a sloped roof, surrounded by a field of white daisies.

A gazebo with a wooden roof and white curtains, surrounded by lush greenery and autumn-colored trees.

A sunlit room with large windows, a dining table, chairs, and a sofa.

3. Country Willows Inn and Estate

Ashland

$215

$219 total

includes taxes & fees

Nov 1 - Nov 2

A garden pathway with wisteria and red flowers, surrounded by lush greenery.

A cozy library with bookshelves, a fireplace, and comfortable seating.

A garden with a red pergola, a stone fountain, and purple flowers.

A bedroom with a bed, a nightstand, a lamp, a chair, a potted plant, and a door.

4. Arden Forest Inn

Ashland

$152

$169 total

includes taxes & fees

Nov 4 - Nov 5

A two-story house with a porch, surrounded by a well-maintained garden with various flowers and shrubs.

A porch with three wooden chairs with floral upholstery, a wooden bench, and a view of a house in the background.

A spacious dining area with a wooden table and chairs, large windows with a view of the outdoors, and a chandelier.

A garden pathway leading to a building with a pergola and hanging flower baskets.

5. Abigail’s Bed & Breakfast Inn

Skidmore Academy Historic District

$260

$290 total

includes taxes & fees

Oct 27 - Oct 28

A large, white, multi-story house with a stone foundation, multiple chimneys, and a well-maintained lawn.

A spacious living room with leather sofas, a fireplace, and wooden beams on the ceiling.

A white house with a black gate, outdoor seating, and a stone pathway.

A stone staircase leading up to a white building with a bell tower, surrounded by greenery and a view of hills.

6. Hummingbird Estate Wine & Suites

Central Point

$191

$194 total

includes taxes & fees

Oct 27 - Oct 28

A red brick building with a balcony and a covered entrance.

A spacious living area with a wooden staircase, a red sofa, a potted plant, and a table with a vase.

A cozy living room with a fireplace, leather armchair, and a bookshelf filled with books.

A leopard print sofa with a fluffy white throw, a 'Love more' pillow, a small table with a lamp and flowers, and a tray with glasses and a bottle.

7. Lady Geneva Bed and Breakfast

City Center Medford

$234

$263 total

includes taxes & fees

Oct 27 - Oct 28

An outdoor patio with seating under a pergola, string lights, and a fire pit.

Two people holding wine glasses in a modern living room with a bookshelf and pendant lights.

A hotel entrance with a black door, a '245' sign above, and a 'HELLO' mat at the threshold.

A spacious entryway with a dark wooden door, large windows, a rug, a chair, and a small table with a plant.

8. Magnolia Hotel

Jacksonville Historic District

$147

$163 total

includes taxes & fees

Oct 27 - Oct 28

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Top neighborhoods in Ashland

A rusted metal bridge in a forested area.

A wooden railway bridge with graffiti, surrounded by greenery.

A wooden log cabin with two red-framed windows.

The exterior of Ashland Food Cooperative with a sign reading "Do You Have Your Bags Today?" and a dog and bike free zone sign.

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.

A grassy field with trees and a distant view of rolling hills.

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.

A building with a purple awning labeled "Caldera Tap House" and a sign with a beer mug illustration.

A historic building with a classical facade, a person standing on the steps, and a wheelchair-accessible sign.

A display window with a large red flower and a sign reading "Oregon Shakespeare Festival Welcome Center".

A building corner with ornate architectural details and arched windows overlooking a cityscape.

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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A wood duck standing on rocks with moss and greenery in the background.

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.

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A snowy forest with tall evergreen trees covered in snow.

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.

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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.

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North Mountain Park

8.4/10 (37 reviews)

North Mountain Park is 0.7 mi (1.2 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. Want to stretch your legs some more? Head to Lithia Park, located nearby.

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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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Ashland Library

8.4/10 (126 reviews)

Ashland Library is worth a pic or two when discovering Siskiyou-Hargadine Historic District.

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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.

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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

What's Ashland Like for B&Bs?

Interested in an accommodation in Ashland with a comfy feel where it's easy to meet other travelers? Choose one of our 13 B&Bs available on Hotels.com and enjoy a memorable stay. After a tasty breakfast at your B&B, you'll be set to discover what's unique about this welcoming destination. Visitors to Ashland highly recommend the entertainment choices and restaurants. Consider visiting Allen Elizabethan Theatre, Angus Bowmer Theatre, and Oregon Shakespeare Festival before returning to your bed & breakfast.