The Best Hotels Closest to Winburn Mountain in Ashland for 2026

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Our top choices for Winburn Mountain hotels

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 lobby with leather sofas, a rug, and lamps.

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

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

1. Stratford Inn

Siskiyou-Hargadine Historic District, 6.8 km from Winburn Mountain

David

SAR 275

SAR 307 total

includes taxes & fees

1 Nov - 2 Nov

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

A wooden balcony with a view of a forested area.

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

2. Callahan's Mountain Lodge

11 km from Winburn Mountain

Karen

SAR 473

SAR 537 total

includes taxes & fees

5 Oct - 6 Oct

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

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

A covered outdoor seating area with benches and potted plants.

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

3. Timbers INN and Suites

6.1 km from Winburn Mountain

Robin

SAR 220

SAR 245 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

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

4. Holiday Inn Express & Suites Ashland by IHG

6.8 km from Winburn Mountain

Adam

SAR 383

SAR 427 total

includes taxes & fees

26 Oct - 27 Oct

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.

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

5. Best Western Windsor Inn

7.1 km from Winburn Mountain

Dennis

SAR 399

SAR 445 total

includes taxes & fees

31 Oct - 1 Nov

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

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.

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

6. Prospero's Flagship Inn

6.2 km from Winburn Mountain

Jenny

SAR 231

SAR 257 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

7. Ashland Hills Hotel & Suites

7 km from Winburn Mountain

Krishnaharsha

SAR 426

SAR 513 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

8. Comfort Inn & Suites Ashland

10.7 km from Winburn Mountain

Christina

SAR 422

SAR 429 total

includes taxes & fees

7 Oct - 8 Oct

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

A spacious room with a large dining table, chairs, a sofa, and a coffee table. There are ceiling fans, large windows, and potted plants.

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

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

9. The Peerless Hotel by WanderLodges

Historic Railroad District, 7.2 km from Winburn Mountain

Jaye

SAR 510

SAR 774 total

includes taxes & fees

6 Oct - 7 Oct

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.

10. Ashland Commons Hostel

7.6 km from Winburn Mountain

Brenda

SAR 251

SAR 280 total

includes taxes & fees

6 Oct - 7 Oct

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 modern bedroom with a large bed, bedside tables, and a view of the outdoors.

11. Grandview of Ashland

7.8 km from Winburn Mountain

Sonja

SAR 727

SAR 1,496 total

includes taxes & fees

5 Oct - 6 Oct

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 two-story house with a porch, a staircase, and a garden.

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

12. Lithia Springs Resort

10.2 km from Winburn Mountain

Steven

SAR 299

SAR 379 total

includes taxes & fees

1 Nov - 2 Nov

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

A garden with a pond, stone walls, and various plants.

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

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

13. Country Willows Inn and Estate

5.1 km from Winburn Mountain

raymon

SAR 728

SAR 738 total

includes taxes & fees

1 Nov - 2 Nov

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.

14. Americas Best Value Inn Phoenix Medford

18.5 km from Winburn Mountain

Steven

SAR 255

SAR 287 total

includes taxes & fees

18 Oct - 19 Oct

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.

15. Plaza Inn & Suites at Ashland Creek

7.6 km from Winburn Mountain

Alan

SAR 453

SAR 505 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

16. Ashland Springs Hotel

Historic Downtown District, 7.1 km from Winburn Mountain

Susan

SAR 319

SAR 414 total

includes taxes & fees

1 Nov - 2 Nov

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

A restaurant with multiple tables and booths, large windows with a view of trees, and hanging decorative light fixtures.

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

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

Historic Downtown District, 7.5 km from Winburn Mountain

Dawn

SAR 484

SAR 540 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A compact living space with a kitchenette, a sofa, a coffee maker, and a small refrigerator.

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

18. Palm Cottages

6.3 km from Winburn Mountain

Eric

SAR 716

SAR 799 total

includes taxes & fees

1 Nov - 2 Nov

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

A modern bathroom with a sink, mirror, and toiletries.

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.

19. Paschal Winery

14.5 km from Winburn Mountain

Christine

SAR 498

SAR 1,564 total

includes taxes & fees

12 Oct - 13 Oct

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

A clear swimming pool with a wooden fence, surrounded by lounge chairs.

20. Ashland Motel - Oregon

6.2 km from Winburn Mountain

Madrik A.

SAR 291

SAR 325 total

includes taxes & fees

4 Oct - 5 Oct

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Compare popular hotels close to Winburn Mountain

Property	Property class	Guest rating
Stratford Inn	9.4 Exceptional 1,783 reviews	View
Callahan's Mountain Lodge	8.8 Excellent 1,137 reviews	View
Timbers INN and Suites	8.8 Excellent 1,008 reviews	View
Holiday Inn Express & Suites Ashland by IHG	9.2 Wonderful 1,011 reviews	View
Best Western Windsor Inn	9.0 Wonderful 1,001 reviews	View

Top Winburn Mountain Hotel Reviews

Stratford Inn

10/10 Excellent

"I enjoy the Stratford because it is an attractive and comfortable place to stay and is in walking distance of Ashland’s numerous attractions."

Ashland Motel - Oregon

8/10 Good

"The room itself was cute and clean. The outside and the AC unit were a little dated but worked well. I did really miss having an ice machine but it was clearly stated that was not an offered amenity so it was not a surprise. The staff was wonderful and the description was informative and accurate. A great overall experience."

Ashland Hills Hotel & Suites

8/10 Good

"Overall we enjoyed the stay. Staff was friendly and bed was comfortable. Breakfast was not included which would have been nice."

Plaza Inn & Suites at Ashland Creek

8/10 Good

"If you are attending an Oregon Shakespeare Festival play, this property is beautifully located about a 10-minute walk from the festival grounds, various restaurants, and Lithia Park. My assigned room wasn't one of the best rooms as it had no balcony or view of the river, but it worked very well for me as I was walking to and from the festival grounds and my room was on the ground floor near an entrance to the play route. Covered parking was nice to have. Breakfast was very good, but always the same and served in a very nice room with access to a balcony overlooking the river so nice for summer or early fall. Tiny tubes of shampoo and other amenities worked fine if you were only staying a day but luckily were replenished daily."

Cedarwood Inn of Ashland

10/10 Excellent

"Good location, good value."

Baymont by Wyndham

8/10 Good

"Had a problem with the TV they replaced it the same day."

Best Western Windsor Inn

8/10 Good

"Staff were helpful and pleasant. Breakfast was generous. Bed was comfy."

Palm Cottages

10/10 Excellent

"Cute motel style place. Room was cute and clean. Walking distance (about 1 mile) to downtown Ashland restaurants and shows."

Country Willows Inn and Estate

10/10 Excellent

"Beautiful property with gardens and a heated pool. Great staff, breakfast was inventive and quite tasty. Is 10 minutes from town but easy to drive and no real parking issues even at play times. We will be back next year"

Other attractions near Winburn Mountain

Mount Ashland Ski Area

8.6/10 (228 reviews)

Hit the slopes in Ashland with a visit to Mount Ashland Ski Area. Discover the top-notch restaurants and entertainment choices in this walkable area.

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Lithia Artisans Market

8.8/10 (3 reviews)

You can find out about the history of Ashland with a trip to Lithia Artisans Market. Experience the entertainment choices and lively festivals in this walkable area.

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Bull Gap Lower Trailhead

8.8/10 (3 reviews)

You can take time to visit Bull Gap Lower Trailhead during your travels to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.

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Ariel Ski Lift

6.0/10 (1 review)

You can take time to visit Ariel Ski Lift during your travels to Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.

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Windsor Ski Lift

You can take time to visit Windsor Ski Lift during your travels to Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.

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Comer Ski Lift

7.2/10 (12 reviews)

You can take time to visit Comer Ski Lift during your travels to Ashland. Discover the top-notch restaurants and lively festivals in this walkable area.

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Weisinger Family Winery

You can enjoy a tasting or tour at Weisinger Family Winery during your travels to Ashland. Wander around the area's picturesque gardens or experience its lively festivals.

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Schneider Museum of Art

10.0/10 (1 review)

You can spend time studying the exhibits at Schneider Museum of Art in Ashland. Experience the entertainment choices and lively festivals in this walkable area.

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Frequently asked questions

What's the area like around Winburn Mountain?

Winburn Mountain is located in Ashland. This welcoming area is known for its picturesque gardens and array of dining options. You'll find 200 hotels and other accommodations within a few miles for a convenient home base.

Where is the best place to stay near Winburn Mountain?

Ashland Hills Hotel & Suites is one of the top choices for your stay based on our traveler data, and this hotel offers a restaurant and an outdoor pool. It's located 4.4 mi (7 km) from Winburn Mountain. Other good options within a few miles include Prospero's Flagship Inn and Stratford Inn.

How many hotels are there near Winburn Mountain?

Expedia has 200 hotels and other accommodations a few miles from Winburn Mountain.

If I need to cancel the hotel reservation for my stay near Winburn Mountain, will I receive a refund?

Yes, you'll find most hotel bookings are fully refundable if you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of check in. If you have a non-refundable reservation, you might be able to cancel it and receive a refund within a 24-hour period of booking. Add your dates and click on "Search", then use the filter option "fully refundable" to get the best options available near Winburn Mountain.

Where can I learn more about changing or cancelling my trip in the area near Winburn Mountain?

To find more details about changing or cancelling your stay near Winburn Mountain, head over to our customer service page.

What can I see and do near Winburn Mountain?

You'll want to browse the exhibits at Schneider Museum of Art and ScienceWorks Hands-On Museum. You can check out the local talent at Oregon Cabaret Theatre, Oregon Shakespeare Festival, and Allen Elizabethan Theatre. You might spend a leisurely day outdoors at Lithia Park and North Mountain Park.

Find hotels near Winburn Mountain, Ashland from SAR 245

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winburn Mountain hotels

1. Stratford Inn

2. Callahan's Mountain Lodge

3. Timbers INN and Suites

4. Holiday Inn Express & Suites Ashland by IHG

5. Best Western Windsor Inn

6. Prospero's Flagship Inn

7. Ashland Hills Hotel & Suites

8. Comfort Inn & Suites Ashland

9. The Peerless Hotel by WanderLodges

10. Ashland Commons Hostel

11. Grandview of Ashland

12. Lithia Springs Resort

13. Country Willows Inn and Estate

14. Americas Best Value Inn Phoenix Medford

15. Plaza Inn & Suites at Ashland Creek

16. Ashland Springs Hotel

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

18. Palm Cottages

19. Paschal Winery

20. Ashland Motel - Oregon

Compare popular hotels close to Winburn Mountain

Top Winburn Mountain Hotel Reviews

Stratford Inn

Ashland Motel - Oregon

Ashland Hills Hotel & Suites

Plaza Inn & Suites at Ashland Creek

Cedarwood Inn of Ashland

Baymont by Wyndham

Best Western Windsor Inn

Palm Cottages

Country Willows Inn and Estate

Other attractions near Winburn Mountain

Mount Ashland Ski Area

Lithia Artisans Market

Bull Gap Lower Trailhead

Ariel Ski Lift

Windsor Ski Lift

Comer Ski Lift

Weisinger Family Winery

Schneider Museum of Art

Frequently asked questions