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.

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

1. Stratford Inn

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

David

AED 343

AED 383 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

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

2. Holiday Inn Express & Suites Ashland by IHG

11.6 km from Windsor Ski Lift

Lorenzo

AED 353

AED 393 total

includes taxes & fees

16 Nov - 17 Nov

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

A kitchen with a countertop displaying various food items, a refrigerator, and a coffee machine.

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.

3. Comfort Inn & Suites Ashland

15.9 km from Windsor Ski Lift

Bill

AED 413

AED 419 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

4. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Krishnaharsha

AED 385

AED 466 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 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.

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.

5. Prospero's Flagship Inn

11.4 km from Windsor Ski Lift

Mary

AED 231

AED 257 total

includes taxes & fees

19 Oct - 20 Oct

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

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.

6. Callahan's Mountain Lodge

8.8 km from Windsor Ski Lift

Meena

AED 340

AED 401 total

includes taxes & fees

25 Oct - 26 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 patio with stone flooring, wooden chairs, and a wooden fence in the background.

7. Best Western Windsor Inn

11.9 km from Windsor Ski Lift

Deborah

AED 390

AED 435 total

includes taxes & fees

31 Oct - 1 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 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.

8. Timbers INN and Suites

11.3 km from Windsor Ski Lift

Sarah

AED 231

AED 257 total

includes taxes & fees

3 Nov - 4 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 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.

9. Ashland Springs Hotel

Historic Downtown District, 12.4 km from Windsor Ski Lift

Susan

AED 344

AED 440 total

includes taxes & fees

11 Nov - 12 Nov

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

10. Plaza Inn & Suites at Ashland Creek

12.9 km from Windsor Ski Lift

Bill

AED 426

AED 475 total

includes taxes & fees

1 Nov - 2 Nov

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.

11. Lithia Springs Resort

15.4 km from Windsor Ski Lift

Steven

AED 344

AED 422 total

includes taxes & fees

8 Nov - 9 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 room with a brick wall, wooden floor, green-framed windows, and two upholstered chairs.

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

AED 381

AED 626 total

includes taxes & fees

19 Oct - 20 Oct

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.

13. Winchester Inn

Historic Downtown District, 12.3 km from Windsor Ski Lift

Ellen

AED 491

AED 606 total

includes taxes & fees

26 Oct - 27 Oct

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

AED 243

AED 271 total

includes taxes & fees

19 Oct - 20 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 garden with a pond, stone walls, and various plants.

15. Country Willows Inn and Estate

10 km from Windsor Ski Lift

Diane

AED 712

AED 722 total

includes taxes & fees

1 Nov - 2 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 glass display case containing wine bottles and glasses, a white chair, and a large window with curtains.

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

16. McCall House Boutique Inn

Historic Downtown District, 12.6 km from Windsor Ski Lift

Elizabeth

AED 597

AED 665 total

includes taxes & fees

18 Nov - 19 Nov

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

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

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

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

Historic Downtown District, 12.8 km from Windsor Ski Lift

Marilyn

AED 437

AED 487 total

includes taxes & fees

4 Nov - 5 Nov

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

A modern kitchen with blue cabinets, stainless steel appliances, a built-in oven, and a microwave.

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

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

18. The Mountain Ave House by WanderLodges

12.3 km from Windsor Ski Lift

Joyce

AED 605

AED 1,207 total

includes taxes & fees

2 Nov - 3 Nov

A deck with a fire pit, outdoor seating, and a view of the countryside.

A spacious living room with a large sofa, a coffee table, and a view of the outdoors.

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.

19. Grandview of Ashland

13 km from Windsor Ski Lift

Sonja

AED 750

AED 1,504 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 coffee machine with a digital display, a coffee pot, a cup, and a coffee pod.

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

20. Ashland Motel - Oregon

11.5 km from Windsor Ski Lift

Madrik A.

AED 245

AED 273 total

includes taxes & fees

15 Nov - 16 Nov

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Compare popular hotels close to Windsor Ski Lift

Property	Property class	Guest rating
Stratford Inn	9.4 Exceptional 1,804 reviews	View
Holiday Inn Express & Suites Ashland by IHG	9.2 Wonderful 1,002 reviews	View
Comfort Inn & Suites Ashland	9.0 Wonderful 1,052 reviews	View
Ashland Hills Hotel & Suites	8.8 Excellent 1,560 reviews	View
Prospero's Flagship Inn	8.4 Very good 1,484 reviews	View

Top Windsor Ski Lift Hotel Reviews

Comfort Inn & Suites Ashland

8/10 Good

"Nice, dog-friendly, clean hotel with quick accessible area for pets. Breakfast area a little small with the basic continental items. Staff were very nice"

Callahan's Mountain Lodge

10/10 Excellent

"Loved this spot. Quiet, simple and very well maintained. Logs in the hallways for fires, jet tubs… it’s a dream!"

Stratford Inn

8/10 Good

"Wonderful location and very friendly, helpful staff. However it is the first hotel in 20 years of traveling that didn't have a hair dryer in each room."

Ashland Springs Hotel

8/10 Good

"The staff was friendly and very helpful."

Plaza Inn & Suites at Ashland Creek

10/10 Excellent

"We stayed here on the recommendation of a friend. So glad we did. The room was clean and spacious. Hotel is well-kept and very quiet. Staff was friendly and helpful. Loved the breakfast. Convenient to OSF. Would recommend."

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."

Timbers INN and Suites

10/10 Excellent

"Our room was very clean and comfortable and our staff interaction was great. We’ll definitely stay here again when we come to Ashland."

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 AED 257

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Treat yourself

Be picky

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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. Comfort Inn & Suites Ashland

4. Ashland Hills Hotel & Suites

5. Prospero's Flagship Inn

6. Callahan's Mountain Lodge

7. Best Western Windsor Inn

8. Timbers INN and Suites

9. Ashland Springs Hotel

10. Plaza Inn & Suites at Ashland Creek

11. Lithia Springs Resort

12. The Peerless Hotel by WanderLodges

13. Winchester Inn

14. Ashland Commons Hostel

15. Country Willows Inn and Estate

16. McCall House Boutique Inn

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

18. The Mountain Ave House by WanderLodges

19. Grandview of Ashland

20. Ashland Motel - Oregon

Compare popular hotels close to Windsor Ski Lift

Top Windsor Ski Lift Hotel Reviews

Comfort Inn & Suites Ashland

Callahan's Mountain Lodge

Stratford Inn

Ashland Springs Hotel

Plaza Inn & Suites at Ashland Creek

Ashland Motel - Oregon

Country Willows Inn and Estate

Timbers INN and Suites

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