A stone bridge over a calm stream with autumn leaves.

Winery Hotels in Ashland

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Winery Hotels in Ashland

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

An outdoor patio with a fire pit, seating, and potted plants.

A lobby with leather sofas, a rug, and lamps.

A restaurant with wooden chairs and tables, large windows, and a dragon sculpture.

1. Stratford Inn

Siskiyou-Hargadine Historic District

$89

$100 total

includes taxes & fees

Nov 1 - Nov 2

An outdoor dining area with round tables, white chairs, and umbrellas.

A cozy room with a wooden bathtub, two armchairs, a TV, and a stone fireplace.

A wooden balcony with a view of a forested area.

2. Callahan's Mountain Lodge

Ashland

$107

$124 total

includes taxes & fees

Oct 5 - Oct 6

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

A man sitting at a table with a notebook, writing. The table has a cup, a small plant, and some pumpkins on it.

A living room with a sofa, armchair, coffee table, and a TV. There are plants, a lamp, and a bookshelf.

3. Ashland Commons Hostel

Ashland

$71

$79 total

includes taxes & fees

Oct 4 - Oct 5

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

A spacious living room with large windows, dark wooden flooring, and a cozy seating area with multiple chairs and a bench.

A room with four armchairs, a bench, and a table with a lamp. There are large windows with a view of greenery outside.

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

Historic Downtown District

$129

$144 total

includes taxes & fees

Nov 1 - Nov 2

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

A room with a brick wall, a wooden dresser, a chair, and a bed.

A room with a brick wall, wooden floor, green-framed windows, and two upholstered chairs.

A spacious bedroom with a four-poster bed, wooden furniture, and a view of the outdoors.

5. The Peerless Hotel by WanderLodges

Historic Railroad District

$151

$223 total

includes taxes & fees

Oct 5 - Oct 6

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 grand staircase with wooden balusters and a carpeted landing.

6. Abigail’s Bed & Breakfast Inn

Skidmore Academy Historic District

$260

$290 total

includes taxes & fees

Oct 27 - Oct 28

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

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

A rustic building with a porch, surrounded by lush greenery and a sign indicating it is a forest.

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

7. Arden Forest Inn

Ashland

$180

$201 total

includes taxes & fees

Oct 5 - Oct 6

A deck with a fire pit, outdoor seating, and a view of the countryside.

A bed with a striped bedspread, a blanket, and an open book. There is a window with a view of trees and hills.

A modern kitchen with a central island, large windows, and a dining area with a view.

A spacious living room with a large sofa, a coffee table, and a view of the outdoors.

8. Grandview of Ashland

Ashland

$227

$432 total

includes taxes & fees

Oct 14 - Oct 15

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

A compact kitchen with white cabinets, a dining table with chairs, a refrigerator, and a built-in oven.

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.

9. Hanna's House by WanderLodges

Historic Railroad District

$143

$236 total

includes taxes & fees

Oct 4 - Oct 5

A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

A spacious living room with a large TV, comfortable seating, and a chandelier.

A living room with a glass coffee table, a television, a chair, and a view of mountains through the window.

A two-story house with a prominent staircase leading to the entrance.

10. Barclay Klum House by WanderLodges

Ashland

$140

$284 total

includes taxes & fees

Oct 4 - Oct 5

A spacious kitchen with a central island, bar stools, and a fireplace.

A modern kitchen with a large island, white cabinetry, and a view of the city.

A spacious dining area with a long wooden table and cushioned chairs, a bookshelf, and a fireplace.

A cozy living room with a sofa, a woven hanging chair, a round pouf, and a large abstract painting.

11. Paschal Winery

Talent

$140

$424 total

includes taxes & fees

Oct 8 - Oct 9

A parking lot with a white convertible car, a motel sign, and a building with a blue door.

A compact kitchenette with a microwave, coffee maker, and a small refrigerator. A television is mounted on the wall above the kitchenette.

A motel with multiple blue doors, a parking lot, and a small garden area.

A bedroom with a bed, bedside tables, a nightstand, a bench, and artwork on the wall.

12. The City Center Motel

City Center Medford

$64

$72 total

includes taxes & fees

Oct 11 - Oct 12

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 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.

A deck with outdoor seating, a bar area, and a fire feature.

13. Compass by Margaritaville in Medford

Medford

$152

$183 total

includes taxes & fees

Oct 12 - Oct 13

A living room with a stone fireplace, a gray sofa, a wooden coffee table, and a lamp on a side table.

A sign for Wine Country Inn with a traditional design, surrounded by greenery and a residential building in the background.

A garden with wooden chairs, a pergola, and a house in the background.

A two-story building with a porch, a flagpole with an American flag, and a sign that reads "Visitor Information."

14. Wine Country Inn

Jacksonville

$114

$126 total

includes taxes & fees

Oct 5 - Oct 6

A hotel room with two beds, a desk with a flat-screen TV, a lamp, and a window with curtains.

A billiards room with green-striped wallpaper, a framed black-and-white photo, and a large beer advertisement.

An indoor swimming pool with clear blue water, large windows, and a view of greenery outside.

A compact kitchen with wooden cabinets, a white countertop, a microwave, and two stools.

15. Red Lion Hotel Rogue Regency Medford Airport

Medford

$93

$110 total

includes taxes & fees

Oct 20 - Oct 21

A two-story house with a covered porch and a sign indicating 'KH KUBLI HAUS'.

A covered outdoor seating area with a sofa, a table with a bottle and snacks, and a patterned rug.

A hotel room with a bed, a chair, a side table with a lamp, and a wall-mounted light fixture.

A room with a white sofa, a wooden coffee table, wicker chairs, a large window with curtains, and a wall mural.

16. Kubli Haus

Jacksonville

$294

$325 total

includes taxes & fees

Oct 4 - Oct 5

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

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.

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

17. Lady Geneva Bed and Breakfast

City Center Medford

$241

$271 total

includes taxes & fees

Oct 5 - Oct 6

A kitchen with a stainless steel sink, wooden cabinets, a black stove, and a window with curtains.

A patio with a table set for a meal, surrounded by a wooden fence and a blue chair.

A bathroom with a white sink, mirror, and shower curtain. There is a framed picture on the wall and a window above the shower.

18. Rosewood Studio by WanderLodges

Medford

$119

$185 total

includes taxes & fees

Oct 14 - Oct 15

A room with a table and chairs, a window with blinds, and a wall with a welcome sign.

A room with a wooden dining table, chairs, a TV, a heater, and two beds with patterned bedspreads.

A hotel room with a wooden dresser, a television mounted on the wall, a large window with blinds, and a painting on the wall.

A room with a wooden desk, a television mounted on the wall, a refrigerator, a microwave, and a large framed picture of a landscape.

19. Travelers Inn Medford

Medford

$71

$82 total

includes taxes & fees

Oct 5 - Oct 6

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

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

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

A modern kitchen with a dining area, featuring a white table, black chairs, and a wooden floor.

20. Magnolia Hotel

Jacksonville Historic District

$165

$183 total

includes taxes & fees

Nov 3 - Nov 4

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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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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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