The Best Hotels Closest to Windsor Ski Lift in Ashland for 2026

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Our top choices for Windsor Ski Lift 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 restaurant with wooden chairs and tables, large windows, and a dragon sculpture.

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

1. Stratford Inn

Siskiyou-Hargadine Historic District, 12.1 km from Windsor Ski Lift

David

AED 269

AED 300 total

includes taxes & fees

2 Nov - 3 Nov

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

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

A wooden balcony with a view of a forested area.

2. Callahan's Mountain Lodge

8.8 km from Windsor Ski Lift

Karen

AED 370

AED 430 total

includes taxes & fees

4 Oct - 5 Oct

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

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.

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

3. Comfort Inn & Suites Ashland

15.9 km from Windsor Ski Lift

Christina

AED 403

AED 409 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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.

4. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Krishnaharsha

AED 393

AED 475 total

includes taxes & fees

2 Nov - 3 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.

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

5. Ashland Commons Hostel

12.9 km from Windsor Ski Lift

Brenda

AED 261

AED 291 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

6. Best Western Windsor Inn

11.9 km from Windsor Ski Lift

Dennis

AED 390

AED 435 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 entrance with a sign, a pedestrian crossing sign, and a road with 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 wooden deck with white lounge chairs and a table, surrounded by a wooden fence and trees.

7. Prospero's Flagship Inn

11.4 km from Windsor Ski Lift

Jenny

AED 226

AED 252 total

includes taxes & fees

2 Nov - 3 Nov

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

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

8. The Peerless Hotel by WanderLodges

Historic Railroad District, 12.6 km from Windsor Ski Lift

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

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

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

9. Plaza Inn & Suites at Ashland Creek

12.9 km from Windsor Ski Lift

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

10. Country Willows Inn and Estate

10 km from Windsor Ski Lift

raymon

AED 712

AED 722 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A covered outdoor seating area with benches and potted plants.

11. Timbers INN and Suites

11.3 km from Windsor Ski Lift

Robin

AED 198

AED 220 total

includes taxes & fees

18 Oct - 19 Oct

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.

12. Holiday Inn Express & Suites Ashland by IHG

11.6 km from Windsor Ski Lift

Adam

AED 353

AED 393 total

includes taxes & fees

2 Nov - 3 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.

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

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

Historic Downtown District, 12.8 km from Windsor Ski Lift

Dawn

AED 474

AED 528 total

includes taxes & fees

1 Nov - 2 Nov

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

A building with a stone facade, a glass door entrance, and a visible interior with a counter and signage.

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

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

14. Baymont by Wyndham

11.7 km from Windsor Ski Lift

Brian

AED 311

AED 346 total

includes taxes & fees

4 Oct - 5 Oct

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 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.

15. Palm Cottages

11.6 km from Windsor Ski Lift

Eric

AED 701

AED 781 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.

16. Lithia Springs Resort

15.4 km from Windsor Ski Lift

Steven

AED 293

AED 371 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

17. Ashland Motel - Oregon

11.5 km from Windsor Ski Lift

Madrik A.

AED 285

AED 318 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

18. Winchester Inn

Historic Downtown District, 12.3 km from Windsor Ski Lift

Deirdre

AED 494

AED 609 total

includes taxes & fees

27 Oct - 28 Oct

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 garden pathway leading to a building with a pergola and hanging flower baskets.

A spacious dining area with a wooden table and chairs, large windows with a view of the outdoors, and a chandelier.

19. Abigail’s Bed & Breakfast Inn

Skidmore Academy Historic District, 13.4 km from Windsor Ski Lift

Kim

AED 955

AED 1,065 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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

20. Cedarwood Inn of Ashland

10.9 km from Windsor Ski Lift

Toby

AED 334

AED 373 total

includes taxes & fees

6 Oct - 7 Oct

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Compare popular hotels close to Windsor Ski Lift

Property	Property class	Guest rating
Stratford Inn	9.4 Exceptional 1,785 reviews	View
Callahan's Mountain Lodge	8.8 Excellent 1,138 reviews	View
Comfort Inn & Suites Ashland	9.0 Wonderful 1,032 reviews	View
Ashland Hills Hotel & Suites	8.8 Excellent 1,532 reviews	View
Ashland Commons Hostel	9.4 Exceptional 74 reviews	View

Top Windsor Ski Lift Hotel Reviews

Holiday Inn Express & Suites Ashland by IHG

8/10 Good

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

Relax Inn At Ashland

10/10 Excellent

"Reasonable prices, total cleanness, responsive staff."

Callahan's Mountain Lodge

10/10 Excellent

"The new smaller portion menu is a plus and minus. Less food, same price. No add one is a big minus. I miss Shawn, the bartender, he gave it a step up..I miss the breakfast included, the new management does not do any bonues to people staying over night. We were on a time crunch and could not do a full service breakfast plus costs. The al a catre or grab and go way one of our reasons for using Callahans as our stop over. Our room was okish. I don't like the soap/shampoo/conditioner dispensers. Since 2 of the 3 were missing. Our room had a broken lock, so I could not get into my room with the key card. The new management needs to upgrade the locks on all doors, take care of guests and make sure all of the amenities are available. We talked to staff, they are happy with the new management, they are taken care of, in return, the guests are suffering. We've stayed her many times. We see good and bad with the new management. Usually I would give a 5 star review, I think with our current experience, it's maybe a 3+ish. We drive to pnw 3-5 times a year. Next time we might power through to a better location with better amenities, for the same price. I'm sad to leave this honest review, because we have always loved Callahans. We've referred Callahans. This last trip was sub par. All of the staff are wonderful, I fully think this is a management issue. Not a staff issue. On a positive side note, Sunshine, the server is a ray of sunshine. Thank you"

Cedarwood Inn of Ashland

8/10 Good

"I like the new improvements. But curtains didn’t cover all the length of the windiws"

Comfort Inn & Suites Ashland

8/10 Good

"We would definitely stay here again"

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."

Baymont by Wyndham

8/10 Good

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

Other attractions near Windsor Ski Lift

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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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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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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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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Winburn Mountain

Commune with nature and explore the great outdoors at Winburn Mountain during your travels in Ashland. Experience the area's entertainment choices and lively festivals.

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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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Tashi Choling Buddhist Center

7.6/10 (4 reviews)

Find out about the history of Ashland when you take a trip to Tashi Choling Buddhist Center. Wander around the area's picturesque gardens or experience its acclaimed theater scene.

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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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Frequently asked questions

What's the area like around Windsor Ski Lift?

Windsor Ski Lift is located in a family-friendly area of Ashland known for its picturesque gardens and array of dining options. Ashland is home to 303 hotels and other accommodations, so you can find something that's perfect for your stay.

Where is the best place to stay near Windsor Ski Lift?

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. You'll find it 7.3 mi (11.8 km) from Windsor Ski Lift. Other good choices in the area include Prospero's Flagship Inn and Callahan's Mountain Lodge.

If I need to cancel the hotel reservation for my stay near Windsor Ski Lift, will I receive a refund?

Yes, most hotel bookings are fully refundable as long as you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If you have a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of booking. Plug in your dates, click on "Search", then you can use the "fully refundable" filter to get the top deals on offer near Windsor Ski Lift.

Where can I learn more about changing or cancelling my trip in the area near Windsor Ski Lift?

For more details about picking new dates or cancelling your stay near Windsor Ski Lift, click here.

What can I see and do near Windsor Ski Lift?

Explore nature at Bull Gap Lower Trailhead and Winburn Mountain. If you're looking for something to do, plan a visit to Mount Ashland Ski Area, Comer Ski Lift, and Ariel Ski Lift while you're in the area. If you want to see more of the surrounding area, you can plan a visit to Tashi Choling Buddhist Center and Lithia Artisans Market.

Find hotels near Windsor Ski Lift, Ashland from AED 220

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Our top choices for Windsor Ski Lift hotels

1. Stratford Inn

2. Callahan's Mountain Lodge

3. Comfort Inn & Suites Ashland

4. Ashland Hills Hotel & Suites

5. Ashland Commons Hostel

6. Best Western Windsor Inn

7. Prospero's Flagship Inn

8. The Peerless Hotel by WanderLodges

9. Plaza Inn & Suites at Ashland Creek

10. Country Willows Inn and Estate

11. Timbers INN and Suites

12. Holiday Inn Express & Suites Ashland by IHG

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

14. Baymont by Wyndham

15. Palm Cottages

16. Lithia Springs Resort

17. Ashland Motel - Oregon

18. Winchester Inn

19. Abigail’s Bed & Breakfast Inn

20. Cedarwood Inn of Ashland

Compare popular hotels close to Windsor Ski Lift

Top Windsor Ski Lift Hotel Reviews

Holiday Inn Express & Suites Ashland by IHG

Relax Inn At Ashland

Callahan's Mountain Lodge

Cedarwood Inn of Ashland

Comfort Inn & Suites Ashland

Ashland Motel - Oregon

Ashland Hills Hotel & Suites

Plaza Inn & Suites at Ashland Creek

Baymont by Wyndham

Other attractions near Windsor Ski Lift

Mount Ashland Ski Area

Comer Ski Lift

Ariel Ski Lift

Bull Gap Lower Trailhead

Winburn Mountain

Lithia Artisans Market

Tashi Choling Buddhist Center

Weisinger Family Winery

Frequently asked questions