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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

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

1. Stratford Inn

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

David

AED 289

AED 323 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 covered outdoor seating area with benches and potted plants.

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.

2. Timbers INN and Suites

11.3 km from Windsor Ski Lift

Robin

AED 198

AED 220 total

includes taxes & fees

15 Oct - 16 Oct

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.

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

3. Callahan's Mountain Lodge

8.8 km from Windsor Ski Lift

Karen

AED 448

AED 510 total

includes taxes & fees

26 Oct - 27 Oct

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 breakfast bar with a toaster, fruit bowl, bread baskets, and a display case with pastries.

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.

4. Prospero's Flagship Inn

11.4 km from Windsor Ski Lift

Karla

AED 210

AED 234 total

includes taxes & fees

11 Oct - 12 Oct

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

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.

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

A hotel with a swimming pool, multiple balconies, and a view of the surrounding landscape.

A spacious living room with a high ceiling, large windows, and a mix of seating arrangements including a sofa and chairs.

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

6. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Krishnaharsha

AED 402

AED 485 total

includes taxes & fees

2 Nov - 3 Nov

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

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

7. Holiday Inn Express & Suites Ashland by IHG

11.6 km from Windsor Ski Lift

Adam

AED 353

AED 393 total

includes taxes & fees

3 Nov - 4 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 kitchen with a countertop displaying various food items, a refrigerator, and a coffee machine.

8. Comfort Inn & Suites Ashland

15.9 km from Windsor Ski Lift

Christina

AED 426

AED 433 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.

9. Ashland Commons Hostel

12.9 km from Windsor Ski Lift

Sam

AED 261

AED 291 total

includes taxes & fees

7 Oct - 8 Oct

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

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

A bar area with a marble countertop, wine bottles, and glasses. There are hanging pendant lights and a 'No Minors' sign.

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

10. Lithia Springs Resort

15.4 km from Windsor Ski Lift

Steven

AED 293

AED 371 total

includes taxes & fees

1 Nov - 2 Nov

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

A building with a snow-covered entrance and a tree in the foreground.

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.

11. Ashland Springs Hotel

Historic Downtown District, 12.4 km from Windsor Ski Lift

Susan

AED 312

AED 405 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

12. The Peerless Hotel by WanderLodges

Historic Railroad District, 12.6 km from Windsor Ski Lift

Jaye

AED 487

AED 744 total

includes taxes & fees

7 Oct - 8 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 hotel room with a bed, a sofa, a table with a bottle, glasses, and a fruit basket.

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

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

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

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

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

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

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

A living room with a fireplace, two armchairs, a sofa, and a TV mounted on the wall.

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

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

A bedroom with a bed, a nightstand, a lamp, a chair, a potted plant, and a door.

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

16. Arden Forest Inn

13.3 km from Windsor Ski Lift

Thomas

AED 595

AED 663 total

includes taxes & fees

14 Oct - 15 Oct

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, 12.8 km from Windsor Ski Lift

Stephen

AED 474

AED 528 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

18. Ashland Motel - Oregon

11.5 km from Windsor Ski Lift

Madrik A.

AED 266

AED 297 total

includes taxes & fees

18 Oct - 19 Oct

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 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.

19. Baymont by Wyndham

11.7 km from Windsor Ski Lift

Brian

AED 311

AED 346 total

includes taxes & fees

12 Oct - 13 Oct

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 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.

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

20. Palm Cottages

11.6 km from Windsor Ski Lift

Eric

AED 701

AED 781 total

includes taxes & fees

1 Nov - 2 Nov

View all properties

Compare popular hotels close to Windsor Ski Lift

Property	Property class	Guest rating
Stratford Inn	9.4 Exceptional 1,796 reviews	View
Timbers INN and Suites	8.8 Excellent 1,000 reviews	View
Callahan's Mountain Lodge	8.8 Excellent 1,140 reviews	View
Prospero's Flagship Inn	8.4 Very good 1,477 reviews	View
Best Western Windsor Inn	9.0 Wonderful 1,006 reviews	View

Top Windsor Ski Lift Hotel Reviews

Ashland Hills Hotel & Suites

10/10 Excellent

"The room was very cleann and quiet."

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."

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."

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."

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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

Filter by

Star rating

Guest rating

Our top choices for Windsor Ski Lift hotels

1. Stratford Inn

2. Timbers INN and Suites

3. Callahan's Mountain Lodge

4. Prospero's Flagship Inn

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 Commons Hostel

10. Lithia Springs Resort

11. Ashland Springs Hotel

12. The Peerless Hotel by WanderLodges

13. Plaza Inn & Suites at Ashland Creek

14. Country Willows Inn and Estate

15. Winchester Inn

16. Arden Forest Inn

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

18. Ashland Motel - Oregon

19. Baymont by Wyndham

20. Palm Cottages

Compare popular hotels close to Windsor Ski Lift

Top Windsor Ski Lift Hotel Reviews

Ashland Hills Hotel & Suites

Ashland Springs Hotel

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

Palm Cottages

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