Business Hotels in Ashland

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Business Hotels in Ashland

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

A hotel entrance with a sign, a pedestrian crossing sign, and a road with trees.

A wooden deck with white lounge chairs and a table, surrounded by a wooden fence and trees.

A breakfast bar with a toaster, fruit bowl, bread baskets, and a display case with pastries.

Prospero's Flagship Inn

Ashland

$62

$69 total

includes taxes & fees

Sep 7 - Sep 8

A spacious lobby with a large wooden floor, a green peace sign decoration, and a large window offering a view of the outdoors.

A bar area with a high ceiling, a TV mounted on the wall, and a bar counter with various bottles.

A spacious living room with a high ceiling, large windows, and a mix of seating arrangements including a sofa and chairs.

A hotel with a swimming pool, multiple balconies, and a view of the surrounding landscape.

Ashland Hills Hotel & Suites

Ashland

$129

$154 total

includes taxes & fees

Sep 7 - Sep 8

A modern hotel room with a dark wood wardrobe, a black refrigerator, a microwave, a sink, and a chair.

A Holiday Inn Express hotel with a modern design, featuring a prominent entrance and a parking lot.

An indoor swimming pool with clear water, a diving board, and a lifeguard sign.

A hotel lobby with a reception desk, seating area, and a view of the hallway.

Holiday Inn Express & Suites Ashland by IHG

Ashland

$117

$130 total

includes taxes & fees

Sep 28 - Sep 29

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

A hotel room with a bed, a desk with a TV, a chair, and a microwave.

A hotel lobby with a reception desk, blue upholstered sofas, a patterned carpet, and a decorative wall.

A kitchen with a countertop displaying various food items, a refrigerator, and a coffee machine.

Comfort Inn & Suites Ashland

Ashland

$110

$111 total

includes taxes & fees

Sep 28 - Sep 29

A pool area with lounge chairs and a hot tub, surrounded by a building with a balcony and stairs.

A restaurant with high ceilings, large windows, and a mix of seating arrangements including tables and booths.

A hotel room with a large bed, a separate sitting area, a large bathtub, and a flat-screen TV.

Best Western Windsor Inn

Ashland

$113

$125 total

includes taxes & fees

Sep 21 - Sep 22

An outdoor patio area with tables and chairs, string lights, and potted plants.

A spacious lobby with a grand chandelier, a fireplace, and a large window offering a view of the outdoors.

A spacious lobby with a high ceiling, ornate chandelier, and multiple seating areas.

A building with a snow-covered entrance and a tree in the foreground.

Ashland Springs Hotel

Historic Downtown District

$197

$235 total

includes taxes & fees

Sep 27 - Sep 28

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

A traditional living room with a fireplace, patterned furniture, and large windows with curtains.

A multi-story hotel with a balcony and outdoor seating area, surrounded by lush greenery and a mountainous backdrop.

A room with a large puzzle on a table, a lamp, a chair, a plant, and a window with a view of a building.

Plaza Inn & Suites at Ashland Creek

Ashland

$179

$200 total

includes taxes & fees

Sep 7 - Sep 8

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

A swimming pool with a wooden deck, a lifebuoy, and white plastic chairs.

A home office with a desk, computer, and office chair. There is a brown leather sofa and a patterned rug.

A room with a desk, computer, office chair, and a bookshelf. There are three doors with blinds, a patterned rug, and a potted plant.

Cedarwood Inn of Ashland

Ashland

$97

$108 total

includes taxes & fees

Sep 6 - Sep 7

A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

A single-story house with a covered porch, a small garden with rocks and a tree, and a mailbox.

A spacious living room with a wooden floor, a sofa, a dining table, and a kitchen area visible through an open doorway.

A compact kitchen with white cabinets, a microwave, and a sink. There is a dining area with a wooden table and chairs, and a small seating area with a blue chair and a table.

Hanna's House by WanderLodges

Historic Railroad District

$179

$277 total

includes taxes & fees

Sep 10 - Sep 11

Two rocking chairs facing a pond with a waterfall, surrounded by lush greenery and wooden fences.

A kitchen with wooden cabinets, a built-in dishwasher, a large island with a wooden countertop, and a view of the outdoors through large windows.

A room with a television, a wooden table with a lamp, a chair, and a small plant. There is a wooden door leading to an outdoor area with a chair and a table.

A traditional living room with a fireplace, red sofas, a coffee table, and a patterned rug.

A Cowslip's Belle Inn

Ashland

$223

$304 total

includes taxes & fees

Sep 7 - Sep 8

A spacious lobby with a plush sofa, a reception desk, and large windows offering a view of the outdoors.

A modern dining area with black leather chairs and tables, a kitchen area with a coffee machine, and a decorative plant centerpiece.

A hotel room with two beds, a desk, a chair, a window with curtains, and artwork on the walls.

A multi-story building with a blue roof, labeled as 'Americas Best Value Inn by Vantage.'

Americas Best Value Inn Phoenix Medford

Phoenix

$80

$90 total

includes taxes & fees

Sep 29 - Sep 30

An outdoor seating area with wicker furniture, a stone wall, and a fire feature.

A hotel reception desk with a modern design, including a wooden panel wall, a large decorative wall piece, and a digital kiosk.

A Fairfield Inn & Suites hotel with a modern design, featuring a prominent entrance and a stone pillar.

A modern lounge area with a stone wall, a flat-screen TV, a fireplace, and comfortable seating.

Fairfield Inn & Suites by Marriott Medford

Medford

$129

$145 total

includes taxes & fees

Sep 6 - Sep 7

A hotel lobby with seating areas, a television, and a bowl of fruit on a table.

A swimming pool with a blue tiled edge, a pool lift, and a lifeguard chair.

A hotel room with two beds, a desk, a chair, a TV, and a wardrobe.

A self-service breakfast area with a refrigerated display case, a coffee machine, and various food items.

Holiday Inn Express Hotel & Suites Medford-Central Point by IHG

Central Point

$95

$107 total

includes taxes & fees

Oct 4 - Oct 5

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

A modern living room with a stone fireplace, blue walls, and patterned furniture.

A hotel room with a large mirror, a sink, a bed, a desk, and a chair.

A kitchen counter with a stone backsplash, coffee makers, and various kitchen items.

Best Western Crater Lake Highway White City/Medford

White City

$95

$97 total

includes taxes & fees

Oct 4 - Oct 5

A modern hotel lobby with multiple seating areas, including round tables and chairs, and a bar area with stools.

A bar area with wooden slats, a flat-screen TV, and stools.

A modern hotel with a two-story structure, a covered entrance, and a parking lot.

A reception area with a wooden reception desk, a modern chair, and a large window with blinds.

Springhill Suites By Marriott Medford Airport

Medford

$110

$123 total

includes taxes & fees

Sep 27 - Sep 28

A Comfort Inn sign surrounded by autumn leaves.

A hotel lobby with a reception desk, seating area, and a television mounted on the wall.

A hotel room with a large bed, two bedside tables, a nightstand, a mirror, and a wall-mounted lamp.

A hotel room with a blue sofa, a wooden table, a bed with a blue and white bedspread, a desk with a lamp, and two framed pictures on the wall.

Comfort Inn South

Medford

$88

$99 total

includes taxes & fees

Oct 4 - Oct 5

A spacious indoor seating area with blue sofas and round tables, large windows with a view of the beach and umbrellas, and a flat-screen TV mounted on the wall.

A hotel room with two beds, a desk, a TV, and a window with a view of the mountains.

A spacious indoor area with a long table and chairs, large windows with a view of the beach, and a bar area.

A hotel lobby with a wooden reception desk, a large chandelier, and a compass-themed floor design.

Compass by Margaritaville in Medford

Medford

$161

$193 total

includes taxes & fees

Sep 6 - Sep 7

A modern hotel room with a dining table, a sofa, a TV, a desk, and a kitchen area with a refrigerator and dishwasher.

A compact kitchen with a refrigerator, microwave, and dishwasher, a small dining table with chairs, and a large mirror on the wall.

A lobby with a sectional sofa, a small table, a television, and a patterned rug.

A gym with treadmills, ellipticals, and weight machines.

Candlewood Suites Medford by IHG

Medford

$101

$114 total

includes taxes & fees

Oct 4 - Oct 5

A modern hotel lobby with a reception desk, seating area, and a fireplace.

A modern hotel lobby with a curved seating area, a fireplace, and a mix of tables and chairs.

A hotel reception area with a reception desk, a flat-screen TV mounted on the wall, and a seating area with chairs.

A modern hotel with a prominent American flag, a covered entrance, and a sign reading "Springhill Suites by Wyndham."

SpringHill Suites by Marriott Medford

Medford

$116

$131 total

includes taxes & fees

Sep 27 - Sep 28

A Courtyard hotel with a covered entrance, a van, and a parking lot.

A modern hotel lobby with a reception desk, a seating area, and a large screen displaying information.

A modern living room with a sectional sofa, a coffee table, and a fireplace.

An outdoor patio area with tables and chairs, a pergola with lights, and a view of the cityscape in the background.

Courtyard by Marriott Medford Airport

Medford

$123

$139 total

includes taxes & fees

Sep 11 - Sep 12

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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 pond with ducks, surrounded by trees and a small bridge.

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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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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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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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, Oregon Shakespeare Festival, Oregon Cabaret Theatre, and Angus Bowmer Theatre are all a short walk away.

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Angus Bowmer Theatre

10.0/10 (11 reviews)

If you want to see a show while you're in town, try and grab some tickets at Angus Bowmer Theatre in Historic Downtown District. If you enjoy the show and want to see another, Allen Elizabethan Theatre, Oregon Shakespeare Festival, and Oregon Cabaret Theatre are all a short walk away.

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