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.

A hotel sign with the name "Straford Inn" and a stone pillar.

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

1. Stratford Inn

Siskiyou-Hargadine Historic District, 6.8 km from Winburn Mountain

David

AED 289

AED 323 total

includes taxes & fees

1 Nov - 2 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 breakfast bar with a toaster, fruit bowl, bread baskets, and a display case with pastries.

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

2. Prospero's Flagship Inn

6.2 km from Winburn Mountain

Karla

AED 210

AED 234 total

includes taxes & fees

11 Oct - 12 Oct

A hotel room with a large bed, a separate bathroom with a bathtub, a window with curtains, and a view of the outdoors.

A wooden balcony with a view of a forested area.

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

3. Callahan's Mountain Lodge

11 km from Winburn Mountain

Karen

AED 392

AED 453 total

includes taxes & fees

6 Oct - 7 Oct

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 covered outdoor seating area with benches and potted plants.

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

4. Timbers INN and Suites

6.1 km from Winburn Mountain

Robin

AED 198

AED 220 total

includes taxes & fees

20 Oct - 21 Oct

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

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

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

AED 390

AED 435 total

includes taxes & fees

31 Oct - 1 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 bar area with a high ceiling, a TV mounted on the wall, and a bar counter with various bottles.

An outdoor patio with lounge chairs and a table, surrounded by autumn foliage and a view of mountains.

6. Ashland Hills Hotel & Suites

7 km from Winburn Mountain

Krishnaharsha

AED 406

AED 490 total

includes taxes & fees

2 Nov - 3 Nov

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 multi-story building with a modern architectural design, featuring a mix of balconies and windows.

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

7. Holiday Inn Express & Suites Ashland by IHG

6.8 km from Winburn Mountain

Adam

AED 353

AED 393 total

includes taxes & fees

2 Nov - 3 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 gray sofa, a small wooden table, a framed picture on the wall, a floor lamp, and a carpeted floor.

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

8. Comfort Inn & Suites Ashland

10.7 km from Winburn Mountain

Christina

AED 403

AED 409 total

includes taxes & fees

3 Nov - 4 Nov

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

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

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.

9. Ashland Springs Hotel

Historic Downtown District, 7.1 km from Winburn Mountain

Susan

AED 312

AED 405 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

10. Lithia Springs Resort

10.2 km from Winburn Mountain

Steven

AED 293

AED 371 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

11. Ashland Commons Hostel

7.6 km from Winburn Mountain

Brenda

AED 259

AED 288 total

includes taxes & fees

18 Oct - 19 Oct

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

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

12. The Peerless Hotel by WanderLodges

Historic Railroad District, 7.2 km from Winburn Mountain

Jaye

AED 499

AED 757 total

includes taxes & fees

6 Oct - 7 Oct

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

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

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

A hotel room with a bed, a sofa, a table with a bottle, glasses, and a fruit basket.

13. Plaza Inn & Suites at Ashland Creek

7.6 km from Winburn Mountain

Alan

AED 443

AED 494 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

14. Country Willows Inn and Estate

5.1 km from Winburn Mountain

raymon

AED 712

AED 722 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

Historic Downtown District, 7.5 km from Winburn Mountain

Stephen

AED 474

AED 528 total

includes taxes & fees

1 Nov - 2 Nov

A large, two-story house with a wrap-around porch and a steeply pitched roof.

A kitchen with a built-in island, pendant lighting, and a view into the dining area.

A modern living room with a sofa, coffee table, and a TV. There is a large window with curtains, a mirror, and a view of a bedroom.

A bar with multiple shelves of bottles, tables, and chairs arranged for patrons.

16. Winchester Inn

Historic Downtown District, 6.9 km from Winburn Mountain

Deirdre

AED 499

AED 616 total

includes taxes & fees

5 Nov - 6 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.

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

17. Americas Best Value Inn Phoenix Medford

18.5 km from Winburn Mountain

Steven

AED 250

AED 281 total

includes taxes & fees

18 Oct - 19 Oct

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

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.

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

18. Arden Forest Inn

7.9 km from Winburn Mountain

Thomas

AED 578

AED 644 total

includes taxes & fees

5 Nov - 6 Nov

A modern kitchen with wooden beams, a dining area with a rug, and a large island.

A two-story house with a blue exterior, a red roof, and a front porch.

A wooden staircase leading to a kitchen with a central island and bar stools.

A bedroom with a bed, a wooden floor, a patterned rug, a sofa, and a wardrobe.

19. The Mountain Ave House by WanderLodges

7 km from Winburn Mountain

Joyce

AED 790

AED 1,413 total

includes taxes & fees

7 Oct - 8 Oct

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

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

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.

20. Ashland Motel - Oregon

6.2 km from Winburn Mountain

Madrik A.

AED 266

AED 297 total

includes taxes & fees

19 Oct - 20 Oct

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Compare popular hotels close to Winburn Mountain

Property	Property class	Guest rating
Stratford Inn	9.4 Exceptional 1,792 reviews	View
Prospero's Flagship Inn	8.4 Very good 1,476 reviews	View
Callahan's Mountain Lodge	8.8 Excellent 1,140 reviews	View
Timbers INN and Suites	8.8 Excellent 1,000 reviews	View
Best Western Windsor Inn	9.0 Wonderful 1,005 reviews	View

Top Winburn Mountain Hotel Reviews

Ashland Springs Hotel

10/10 Excellent

"The Ashland Springs Hotel always provides a satisfying experience. It's extremely convenient for visiting the Oregon Shakespeare Festival, and Lark's Restaurant is one of the consistently best in Ashland. The rooms tend to be small (at least the ones we've stayed in). Ours didn't have a dresser, which was a bit inconvenient. The mezzanine is a very nice place to sit and have breakfast or afternoon tea. We will be coming back again."

Stratford Inn

10/10 Excellent

"This property is fun, efficient, has what you need and want but isn't stuffy or pretentious. Beds were comfortable. The pillows... There were options and I made it work. The breakfast the first day was nice. The second day, the hotel was full and items went quickly. But the coffee was good and plenty of it. The location is just right. Out of the fray but close enough to walk to the theaters and many restaurants. Overall, was a great value and function. Hit all the marks I was looking for, for this trip."

Ashland Hills Hotel & Suites

10/10 Excellent

"Great hotel with its retro decor and beautiful location in Ashland! Very clean, nice pool area and friendly staff. I've stayed here before a few years ago - but missing the breakfast that was available before. Otherwise, a very nice stay for our Oregon Shakespeare Festival trip!"

Baymont by Wyndham

10/10 Excellent

"I've stayed here many times now and always a great experience."

Comfort Inn & Suites Ashland

10/10 Excellent

"Lovely stay, room very clean and comfortable, and the staff were all very nice. Will definitely stay there again."

Relax Inn At Ashland

8/10 Good

"Quaint, renovated motel. Nice touches but not high end. Nice location, staff friendly. As rated, would go back. Dog allowed, micro/fridge in room. Great coffee kiosk next door, organic fair trade coffee and organic milk."

Plaza Inn & Suites at Ashland Creek

10/10 Excellent

"Nice location close to the creek and fun eating establishments in town. Free EV charging in the garage was a nice plus."

Holiday Inn Express & Suites Ashland by IHG

8/10 Good

"Great location near I-5. Clean and comfortable room"

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."

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 AED 220

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. Prospero's Flagship Inn

3. Callahan's Mountain Lodge

4. Timbers INN and Suites

5. Best Western Windsor Inn

6. Ashland Hills Hotel & Suites

7. Holiday Inn Express & Suites Ashland by IHG

8. Comfort Inn & Suites Ashland

9. Ashland Springs Hotel

10. Lithia Springs Resort

11. Ashland Commons Hostel

12. The Peerless Hotel by WanderLodges

13. Plaza Inn & Suites at Ashland Creek

14. Country Willows Inn and Estate

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

16. Winchester Inn

17. Americas Best Value Inn Phoenix Medford

18. Arden Forest Inn

19. The Mountain Ave House by WanderLodges

20. Ashland Motel - Oregon

Compare popular hotels close to Winburn Mountain

Top Winburn Mountain Hotel Reviews

Ashland Springs Hotel

Stratford Inn

Ashland Hills Hotel & Suites

Baymont by Wyndham

Comfort Inn & Suites Ashland

Relax Inn At Ashland

Plaza Inn & Suites at Ashland Creek

Holiday Inn Express & Suites Ashland by IHG

Ashland Motel - Oregon

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