Ashland Windsor Ski Lift Hotels: 2026 Limited-Time Hotel Deals @Expedia

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Our top choices for Windsor Ski Lift hotels

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

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.

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

1. Holiday Inn Express & Suites Ashland by IHG

11.6 km from Windsor Ski Lift

Lorenzo

HK$753

HK$840 total

includes taxes & fees

16 Nov - 17 Nov

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.

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

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

2. Stratford Inn

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

David

HK$733

HK$818 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

3. Best Western Windsor Inn

11.9 km from Windsor Ski Lift

Deborah

HK$834

HK$930 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.

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

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

4. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Nicholas

HK$766

HK$932 total

includes taxes & fees

1 Nov - 2 Nov

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.

5. Comfort Inn & Suites Ashland

15.9 km from Windsor Ski Lift

Bill

HK$883

HK$896 total

includes taxes & fees

25 Oct - 26 Oct

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.

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

6. Callahan's Mountain Lodge

8.8 km from Windsor Ski Lift

Meena

HK$728

HK$856 total

includes taxes & fees

25 Oct - 26 Oct

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 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

HK$537

HK$599 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 wooden deck with white lounge chairs and a table, surrounded by a wooden fence and trees.

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

8. Prospero's Flagship Inn

11.4 km from Windsor Ski Lift

Mary

HK$579

HK$646 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 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.

9. Lithia Springs Resort

15.4 km from Windsor Ski Lift

Steven

HK$734

HK$902 total

includes taxes & fees

8 Nov - 9 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 traditional living room with a fireplace, patterned furniture, and large windows with curtains.

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

10. Plaza Inn & Suites at Ashland Creek

12.9 km from Windsor Ski Lift

Bill

HK$911

HK$1,016 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 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.

11. Ashland Commons Hostel

12.9 km from Windsor Ski Lift

Sam

HK$558

HK$622 total

includes taxes & fees

20 Oct - 21 Oct

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

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.

12. The Peerless Hotel by WanderLodges

Historic Railroad District, 12.6 km from Windsor Ski Lift

Jaye

HK$841

HK$1,366 total

includes taxes & fees

20 Oct - 21 Oct

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.

13. Ashland Springs Hotel

Historic Downtown District, 12.4 km from Windsor Ski Lift

Susan

HK$734

HK$941 total

includes taxes & fees

11 Nov - 12 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 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

Diane

HK$1,521

HK$1,543 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

A compact kitchen with white cabinets, a dining table with chairs, a refrigerator, and a built-in oven.

15. Hanna's House by WanderLodges

Historic Railroad District, 12.3 km from Windsor Ski Lift

Robert

HK$770

HK$1,462 total

includes taxes & fees

20 Oct - 21 Oct

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

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

16. The Mountain Ave House by WanderLodges

12.3 km from Windsor Ski Lift

Joyce

HK$1,405

HK$2,704 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

17. Arden Forest Inn

13.3 km from Windsor Ski Lift

Jean

HK$1,271

HK$1,418 total

includes taxes & fees

20 Oct - 21 Oct

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

A modern kitchen with a central island, large windows, and a dining area with a view.

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

A bed with a striped bedspread, a blanket, and an open book. There is a window with a view of trees and hills.

18. Grandview of Ashland

13 km from Windsor Ski Lift

Sonja

HK$1,603

HK$3,213 total

includes taxes & fees

20 Oct - 21 Oct

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.

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

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

Historic Downtown District, 12.8 km from Windsor Ski Lift

Marilyn

HK$934

HK$1,041 total

includes taxes & fees

3 Nov - 4 Nov

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

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

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

A room with a glass display case containing wine bottles and glasses, a white chair, and a large window with curtains.

20. McCall House Boutique Inn

Historic Downtown District, 12.6 km from Windsor Ski Lift

Elizabeth

HK$1,229

HK$1,370 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
Holiday Inn Express & Suites Ashland by IHG	9.2 Wonderful 1,002 reviews	View
Stratford Inn	9.4 Exceptional 1,804 reviews	View
Best Western Windsor Inn	9.0 Wonderful 1,002 reviews	View
Ashland Hills Hotel & Suites	8.8 Excellent 1,561 reviews	View
Comfort Inn & Suites Ashland	9.0 Wonderful 1,055 reviews	View

Top Windsor Ski Lift Hotel Reviews

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

10/10 Excellent

"A great place to stay close to downtown. We were able to walk to lithia park, different places for breakfast, a brewery downtown. A quiet and great location just walking distance from so much!"

Ashland Springs Hotel

10/10 Excellent

"Location is perfect for Ashland."

Callahan's Mountain Lodge

10/10 Excellent

"Room was recently renovated with vinyl flooring. Jacuzzi and fireplace are nice amenities. Large room and balcony with view of the woods. Onsite restaurant serves great food. Staff is very friendly and helpful."

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."

Best Western Windsor Inn

8/10 Good

"Breakfast was nearly empty and not great- staff did not care. Older property, it was reasonably clean but out of date."

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 visit 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 with a stop at Tashi Choling Buddhist Center. Wander around the area's picturesque gardens or experience its acclaimed theatre 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 accommodation options, 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 traveller 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 room reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you might be able to still cancel and get a refund within 24 hours of booking. Add dates, click "Search", then you can filter by "fully refundable" to view the best options available near Windsor Ski Lift.

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.

Ashland Windsor Ski Lift Hotels

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. Holiday Inn Express & Suites Ashland by IHG

2. Stratford Inn

3. Best Western Windsor Inn

4. Ashland Hills Hotel & Suites

5. Comfort Inn & Suites Ashland

6. Callahan's Mountain Lodge

7. Timbers INN and Suites

8. Prospero's Flagship Inn

9. Lithia Springs Resort

10. Plaza Inn & Suites at Ashland Creek

11. Ashland Commons Hostel

12. The Peerless Hotel by WanderLodges

13. Ashland Springs Hotel

14. Country Willows Inn and Estate

15. Hanna's House by WanderLodges

16. The Mountain Ave House by WanderLodges

17. Arden Forest Inn

18. Grandview of Ashland

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

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

Ashland Springs Hotel

Callahan's Mountain Lodge

Stratford Inn

Best Western Windsor Inn

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