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

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

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

1. Stratford Inn

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

David

SAR 351

SAR 391 total

includes taxes & fees

26 Oct - 27 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 multi-story building with a modern architectural design, featuring a mix of balconies and windows.

2. Holiday Inn Express & Suites Ashland by IHG

11.6 km from Windsor Ski Lift

Lorenzo

SAR 360

SAR 402 total

includes taxes & fees

19 Nov - 20 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.

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

3. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Nicholas

SAR 390

SAR 473 total

includes taxes & fees

1 Nov - 2 Nov

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.

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

4. Best Western Windsor Inn

11.9 km from Windsor Ski Lift

Deborah

SAR 399

SAR 444 total

includes taxes & fees

31 Oct - 1 Nov

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

A wooden balcony with a view of a forested area.

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

5. Callahan's Mountain Lodge

8.8 km from Windsor Ski Lift

Meena

SAR 365

SAR 426 total

includes taxes & fees

30 Oct - 31 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.

6. Comfort Inn & Suites Ashland

15.9 km from Windsor Ski Lift

Bill

SAR 421

SAR 427 total

includes taxes & fees

22 Nov - 23 Nov

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

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

7. Timbers INN and Suites

11.3 km from Windsor Ski Lift

Sarah

SAR 234

SAR 261 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 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.

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

8. Prospero's Flagship Inn

11.4 km from Windsor Ski Lift

Mary

SAR 261

SAR 291 total

includes taxes & fees

4 Nov - 5 Nov

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

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.

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

9. Plaza Inn & Suites at Ashland Creek

12.9 km from Windsor Ski Lift

Bill

SAR 435

SAR 486 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

10. Lithia Springs Resort

15.4 km from Windsor Ski Lift

Steven

SAR 351

SAR 431 total

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a bed, bedside table, lamp, and a window with blinds.

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

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

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.

11. Winchester Inn

Historic Downtown District, 12.3 km from Windsor Ski Lift

Ellen

SAR 501

SAR 619 total

includes taxes & fees

9 Nov - 10 Nov

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

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

12. The Peerless Hotel by WanderLodges

Historic Railroad District, 12.6 km from Windsor Ski Lift

Jaye

SAR 349

SAR 594 total

includes taxes & fees

26 Oct - 27 Oct

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

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

13. Country Willows Inn and Estate

10 km from Windsor Ski Lift

Diane

SAR 727

SAR 738 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 living room with a sofa, armchair, coffee table, and a TV. There are plants, a lamp, and a bookshelf.

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

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

14. Ashland Commons Hostel

12.9 km from Windsor Ski Lift

Sam

SAR 251

SAR 280 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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.

15. Ashland Springs Hotel

Historic Downtown District, 12.4 km from Windsor Ski Lift

Duff

SAR 319

SAR 414 total

includes taxes & fees

19 Nov - 20 Nov

A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

A two-story house with a prominent staircase leading to the entrance.

A living room with a glass coffee table, a television, a chair, and a view of mountains through the window.

A spacious living room with a large TV, comfortable seating, and a chandelier.

16. Barclay Klum House by WanderLodges

12.2 km from Windsor Ski Lift

Melissa

SAR 429

SAR 959 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

17. Arden Forest Inn

13.3 km from Windsor Ski Lift

Jean

SAR 513

SAR 572 total

includes taxes & fees

2 Nov - 3 Nov

A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

A compact kitchen with white cabinets, a microwave, and a sink. There is a dining area with a wooden table and chairs, and a small seating area with a blue chair and a table.

A spacious living room with a wooden floor, a sofa, a dining table, and a kitchen area visible through an open doorway.

A single-story house with a covered porch, a small garden with rocks and a tree, and a mailbox.

18. Hanna's House by WanderLodges

Historic Railroad District, 12.3 km from Windsor Ski Lift

Robert

SAR 463

SAR 804 total

includes taxes & fees

2 Nov - 3 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 spacious living room with large windows, dark wooden flooring, and a cozy seating area with multiple chairs and a bench.

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

Historic Downtown District, 12.8 km from Windsor Ski Lift

Thomas

SAR 431

SAR 481 total

includes taxes & fees

7 Nov - 8 Nov

A Victorian-style building with ornate architectural details, large windows, and a red door.

A spacious living room with a large sofa, a dining area with a table and chairs, and a chandelier.

A room with a bay window, two upholstered chairs, a round ottoman, and a small wooden table.

A patio area with string lights, potted plants, and a stone pathway.

20. McCall House Boutique Inn

Historic Downtown District, 12.6 km from Windsor Ski Lift

Elizabeth

SAR 587

SAR 655 total

includes taxes & fees

1 Nov - 2 Nov

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Compare popular hotels close to Windsor Ski Lift

Property	Property class	Guest rating
Stratford Inn	9.4 Exceptional 1,796 reviews	View
Holiday Inn Express & Suites Ashland by IHG	9.2 Wonderful 1,004 reviews	View
Ashland Hills Hotel & Suites	8.8 Excellent 1,563 reviews	View
Best Western Windsor Inn	9.0 Wonderful 1,000 reviews	View
Callahan's Mountain Lodge	8.8 Excellent 1,131 reviews	View

Top Windsor Ski Lift Hotel Reviews

Ashland Springs Hotel

10/10 Excellent

"Location is so nice. Love Ashland. Been staying here for years. Watched this hotel go from wore out to closed to refurbished to new owners over the last 50 years. Love these 1920’s hotels so happy they are keeping it going."

Stratford Inn

10/10 Excellent

"Friendly staff. Room was clean. I was very comfortable. I even bought a mug! Looking forward to next stay."

Plaza Inn & Suites at Ashland Creek

8/10 Good

"There was not enough easily accessible parking and a lot of it was for compact cars. As senior citizens, we found the lower level to be a challenge."

Ashland Motel - Oregon

8/10 Good

"Rooms are clean and have window ac units. Bathroom is a decent size and shower is amply large. Free parking available. No housekeeping offered for first four days and rarely is anyone in the office. On our last day, someone knocked on the door and asked us if we needed housekeeping, but we were leaving the next day so that wasn’t helpful. Desk area is useful and there is an extension cord with multiple outlets by the desk."

Country Willows Inn and Estate

10/10 Excellent

"A beautiful serene landscape compliments the beautifully decorated and very comfy rooms. Beds and pillows were divine. Breakfast was epicurean."

Winchester Inn

10/10 Excellent

"Amazing breakfasts, friendly staff, best location"

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 SAR 261

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Star rating

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Our top choices for Windsor Ski Lift hotels

1. Stratford Inn

2. Holiday Inn Express & Suites Ashland by IHG

3. Ashland Hills Hotel & Suites

4. Best Western Windsor Inn

5. Callahan's Mountain Lodge

6. Comfort Inn & Suites Ashland

7. Timbers INN and Suites

8. Prospero's Flagship Inn

9. Plaza Inn & Suites at Ashland Creek

10. Lithia Springs Resort

11. Winchester Inn

12. The Peerless Hotel by WanderLodges

13. Country Willows Inn and Estate

14. Ashland Commons Hostel

15. Ashland Springs Hotel

16. Barclay Klum House by WanderLodges

17. Arden Forest Inn

18. Hanna's House by WanderLodges

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

20. McCall House Boutique Inn

Compare popular hotels close to Windsor Ski Lift

Top Windsor Ski Lift Hotel Reviews

Ashland Springs Hotel

Stratford Inn

Plaza Inn & Suites at Ashland Creek

Ashland Motel - Oregon

Country Willows Inn and Estate

Winchester Inn

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