2 Star Hotels in Ashland

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2 Star Hotels in Ashland

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.

A patio with stone flooring, wooden chairs, and a wooden fence in the background.

1. Best Western Windsor Inn

Ashland

$106

$118 total

includes taxes & fees

Oct 31 - Nov 1

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

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

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

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

2. Stratford Inn

Siskiyou-Hargadine Historic District

$113

$125 total

includes taxes & fees

Oct 18 - Oct 19

A breakfast buffet area with labeled food stations, including hot food, cereal, and fruit.

A hotel room with a blue sofa, a black coffee table, a bed with white linens, and a large window with curtains.

A hotel bathroom with a wooden door, a sink with a mirror, a towel rack, a coffee maker, and a black refrigerator.

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

3. Holiday Inn Express & Suites Ashland by IHG

Ashland

$102

$114 total

includes taxes & fees

Oct 28 - Oct 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 room with a gray sofa, a small wooden table, a framed picture on the wall, a floor lamp, and a carpeted floor.

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

4. Comfort Inn & Suites Ashland

Ashland

$113

$114 total

includes taxes & fees

Oct 25 - Oct 26

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

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

A hotel room with a large bed, two bedside tables with lamps, a wooden headboard, a framed picture on the wall, a mirror above the sink, and striped carpeting.

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

5. Prospero's Flagship Inn

Ashland

$62

$69 total

includes taxes & fees

Oct 18 - Oct 19

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 kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with stools.

6. Ashland Commons Hostel

Ashland

$71

$79 total

includes taxes & fees

Oct 19 - Oct 20

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

A modern hotel lobby with a leather sofa, a coffee table, a patterned rug, a reception desk, and a wall-mounted snack station.

A hotel room with a large bed, a desk, and a window with curtains.

A Zen garden with a statue, surrounded by various plants and rocks.

7. Timbers INN and Suites

Ashland

$68

$75 total

includes taxes & fees

Nov 1 - Nov 2

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.

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

Historic Downtown District

$125

$139 total

includes taxes & fees

Nov 3 - Nov 4

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

A pathway leading to a building with a decorative archway, surrounded by flowering trees and a well-maintained lawn.

A hotel reception area with a Dell computer, a calendar, and a window with a view of the outside.

A coffee machine with a digital display, a coffee pot, a cup, and a coffee pod.

9. Ashland Motel - Oregon

Ashland

$81

$90 total

includes taxes & fees

Oct 18 - Oct 19

A hotel room with two beds, a large framed picture of a mountain, a lamp, and a window with curtains.

A modern living room with a brown leather sofa, a black coffee table, and a kitchen area with wooden cabinets and a marble backsplash.

A reception area with a wooden counter, a clock, a television, and a window with blinds.

A hotel kitchen with marble tiles, a coffee machine, a refrigerator, and a counter with various items.

10. Baymont by Wyndham

Ashland

$90

$100 total

includes taxes & fees

Oct 16 - Oct 17

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

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.

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

11. The Peerless Hotel by WanderLodges

Historic Railroad District

$127

$197 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.

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

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

A bedroom with a bed, bedside tables, a nightstand, a dresser, a chair, a rug, and a painting on the wall.

12. Cedarwood Inn of Ashland

Ashland

$75

$84 total

includes taxes & fees

Oct 18 - Oct 19

A wooden cabin with a deck and stairs, surrounded by trees.

A spacious living area with large windows, a sofa, a chair, and a wooden floor.

A cozy cabin interior with a wooden table, sofa, and a fireplace.

A wooden deck with a grill, chairs, and a kitchen visible through open doors.

13. Green Springs Inn

Ashland

$82

$108 total

includes taxes & fees

Oct 18 - Oct 19

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a covered seating area.

A dining table set with plates, cutlery, and glasses, with two leather stools and a window with blinds in the background.

A well-maintained garden with a variety of plants and a wooden fence.

A hotel room with a bed, a mirror, a round mirror, a door leading to a bathroom, a nightstand with a lamp, and a framed picture on the wall.

14. Palm Cottages

Ashland

$201

$224 total

includes taxes & fees

Oct 16 - Oct 17

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

A multi-story hotel with a central courtyard, balconies, and a mix of exterior colors.

A modern hotel lobby with a reception desk, seating area, and a large window offering a view of the outdoors.

A hotel room with a bed, a desk, a chair, a nightstand, and a wall-mounted TV.

15. Americas Best Value Inn Phoenix Medford

Phoenix

$68

$77 total

includes taxes & fees

Oct 18 - Oct 19

A modern kitchen with wooden cabinets, a central island, and a black backsplash with 'EAT' written on it.

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

An outdoor patio area with wicker furniture and a wooden fence.

A reception desk with a "Welcome to the Pacific Wonderland" sign, a digital check-in station, and a "Hilton Honors" sign.

16. Hampton Inn Medford

Medford

$101

$114 total

includes taxes & fees

Oct 24 - Oct 25

A modern lobby with seating, a television, and artwork on the walls.

A modern breakfast area with a digital menu board, a coffee machine, and a yogurt dispenser.

A hotel room with two beds, a desk, an orange chair, and a large window.

A Holiday Inn Express & Suites building with a covered entrance, multiple floors, and a parking lot.

17. Holiday Inn Express & Suites Medford by IHG

Medford

$103

$116 total

includes taxes & fees

Nov 15 - Nov 16

A covered outdoor seating area with a table and chairs, surrounded by trees and a building with a red door in the background.

A coffee station with a coffee machine, multiple coffee dispensers, and a variety of coffee pods and bottles.

A motel with a two-story structure, multiple red doors, and a parking area marked "No Parking."

A bedroom with a large bed, a wooden headboard, and three framed landscape paintings on the wall.

18. Crater Lake Gateway - Highway 140

Klamath Falls

$99

$108 total

includes taxes & fees

Oct 18 - Oct 19

A clear view of a lake with a mountain in the background, a dock, and a chair on a deck.

A lodge surrounded by dense forest and a calm lake.

A snowy landscape with tall evergreen trees, a clear blue sky, and a flagpole with an American flag.

A wooden interior with a bar area, leather seating, and large windows offering a view.

19. Rocky Point Resort

Klamath Falls

$95

$108 total

includes taxes & fees

Oct 18 - Oct 19

A river surrounded by dense trees and a grassy area with a clear view of the river.

A Maple Leaf Motel sign with a white picket fence and a red car parked in front.

A hotel room with two beds, a nightstand, wall-mounted lamps, and framed artwork.

A motel with a signboard, a fenced parking area, and a building with a porch.

20. Maple Leaf Motel

Shady Cove

$107

$115 total

includes taxes & fees

Nov 1 - Nov 2

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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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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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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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