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.

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

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 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 bar area with a high ceiling, a TV mounted on the wall, and a bar counter with various bottles.

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

3. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Nicholas

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 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

Mary

AED 261

AED 291 total

includes taxes & fees

3 Nov - 4 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.

5. Comfort Inn & Suites Ashland

15.9 km from Windsor Ski Lift

Bill

AED 413

AED 419 total

includes taxes & fees

26 Oct - 27 Oct

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.

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

6. 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 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.

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

7. 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 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.

8. Timbers INN and Suites

11.3 km from Windsor Ski Lift

Sarah

AED 234

AED 261 total

includes taxes & fees

3 Nov - 4 Nov

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

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.

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

AED 344

AED 422 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 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.

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 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.

11. The Peerless Hotel by WanderLodges

Historic Railroad District, 12.6 km from Windsor Ski Lift

Jaye

AED 393

AED 639 total

includes taxes & fees

20 Oct - 21 Oct

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

12. Ashland Commons Hostel

12.9 km from Windsor Ski Lift

Sam

AED 243

AED 271 total

includes taxes & fees

28 Oct - 29 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 garden with a pond, stone walls, and various plants.

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

13. Country Willows Inn and Estate

10 km from Windsor Ski Lift

Diane

AED 712

AED 722 total

includes taxes & fees

1 Nov - 2 Nov

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

14. 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

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

15. The Mountain Ave House by WanderLodges

12.3 km from Windsor Ski Lift

Joyce

AED 605

AED 1,207 total

includes taxes & fees

26 Oct - 27 Oct

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 dining table with chairs, a refrigerator, and a built-in oven.

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.

16. Hanna's House by WanderLodges

Historic Railroad District, 12.3 km from Windsor Ski Lift

Robert

AED 337

AED 659 total

includes taxes & fees

20 Oct - 21 Oct

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

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.

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

17. Arden Forest Inn

13.3 km from Windsor Ski Lift

Jean

AED 595

AED 663 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 restaurant with multiple tables and booths, large windows with a view of trees, and hanging decorative light fixtures.

18. 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

3 Nov - 4 Nov

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

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

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

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

19. McCall House Boutique Inn

Historic Downtown District, 12.6 km from Windsor Ski Lift

Elizabeth

AED 575

AED 641 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A modern bedroom with a large bed, bedside tables, and a view of the outdoors.

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

20. Grandview of Ashland

13 km from Windsor Ski Lift

Sonja

AED 592

AED 1,342 total

includes taxes & fees

22 Oct - 23 Oct

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Compare popular hotels close to Windsor Ski Lift

Property	Property class	Guest rating
Stratford Inn	9.4 Exceptional 1,807 reviews	View
Holiday Inn Express & Suites Ashland by IHG	9.2 Wonderful 1,002 reviews	View
Ashland Hills Hotel & Suites	8.8 Excellent 1,564 reviews	View
Prospero's Flagship Inn	8.4 Very good 1,486 reviews	View
Comfort Inn & Suites Ashland	9.0 Wonderful 1,055 reviews	View

Top Windsor Ski Lift Hotel Reviews

Stratford Inn

10/10 Excellent

"Fun place to stay. A bit older hotel but the charisma made up for the age. Halloween decorations were a hoot! We weren't expecting breakfast but enjoyed it. Not a full breakfast but delicious stone ground oatmeal, yogurt, bagels and fruit."

Timbers INN and Suites

10/10 Excellent

"I thought this was a great motel. It's across the street from SOU and easy walking to a grocery store (next door) and restaurants. It's also an easy drive to the center of town for Shakespear Festival activities. It was a great place to stay at a fraction of the price of the center of town. It is a motel, so expectations should be adjusted accordingly, but it was clean and seemed well kept. I would definitely stay here again."

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 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."

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"

Baymont by Wyndham

8/10 Good

"It was quiet, clean and reasonably priced. The wi fi worked well in the room"

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 261

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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. Holiday Inn Express & Suites Ashland by IHG

3. Ashland Hills Hotel & Suites

4. Prospero's Flagship Inn

5. Comfort Inn & Suites Ashland

6. Best Western Windsor Inn

7. Callahan's Mountain Lodge

8. Timbers INN and Suites

9. Lithia Springs Resort

10. Plaza Inn & Suites at Ashland Creek

11. The Peerless Hotel by WanderLodges

12. Ashland Commons Hostel

13. Country Willows Inn and Estate

14. Ashland Springs Hotel

15. The Mountain Ave House by WanderLodges

16. Hanna's House by WanderLodges

17. Arden Forest Inn

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

19. McCall House Boutique Inn

20. Grandview of Ashland

Compare popular hotels close to Windsor Ski Lift

Top Windsor Ski Lift Hotel Reviews

Stratford Inn

Timbers INN and Suites

Plaza Inn & Suites at Ashland Creek

Ashland Springs Hotel

Callahan's Mountain Lodge

Ashland Motel - Oregon

Country Willows Inn and Estate

Winchester Inn

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