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

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Our top choices for Windsor Ski Lift hotels

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.

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

1. Callahan's Mountain Lodge

8.8 km from Windsor Ski Lift

Karen

AED 443

AED 505 total

includes taxes & fees

2 Nov - 3 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 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.

2. Timbers INN and Suites

11.3 km from Windsor Ski Lift

Evangelina

AED 200

AED 223 total

includes taxes & fees

19 Oct - 20 Oct

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.

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

AED 390

AED 435 total

includes taxes & fees

31 Oct - 1 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 wooden deck with white lounge chairs and a table, surrounded by a wooden fence and 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.

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

5. Comfort Inn & Suites Ashland

15.9 km from Windsor Ski Lift

Kristi

AED 426

AED 433 total

includes taxes & fees

2 Nov - 3 Nov

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

6. Holiday Inn Express & Suites Ashland by IHG

11.6 km from Windsor Ski Lift

Lorenzo

AED 360

AED 401 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 man sitting at a table with a notebook, writing. The table has a cup, a small plant, and some pumpkins on it.

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

7. Ashland Commons Hostel

12.9 km from Windsor Ski Lift

Sam

AED 245

AED 274 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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.

8. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Krishnaharsha

AED 408

AED 492 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, 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 room with a brick wall, wooden floor, green-framed windows, and two upholstered chairs.

9. The Peerless Hotel by WanderLodges

Historic Railroad District, 12.6 km from Windsor Ski Lift

Jaye

AED 460

AED 713 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 multi-story hotel with a balcony and outdoor seating area, surrounded by lush greenery and a mountainous backdrop.

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.

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

11. 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 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.

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

12. Winchester Inn

Historic Downtown District, 12.3 km from Windsor Ski Lift

Margaret

AED 480

AED 593 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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.

13. Arden Forest Inn

13.3 km from Windsor Ski Lift

Thomas

AED 590

AED 658 total

includes taxes & fees

8 Nov - 9 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-lit room with a sofa, chairs, and a coffee table. There are bookshelves filled with books and decorative items.

14. Lithia Springs Resort

15.4 km from Windsor Ski Lift

Steven

AED 293

AED 371 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 clear swimming pool with a wooden fence, surrounded by lounge chairs.

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

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

16. 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 two beds, a large framed picture of a mountain, a lamp, and a window with curtains.

A building with a stone facade, a glass door entrance, and a visible interior with a counter and signage.

A reception area with a wooden counter, a clock, a television, and a window with blinds.

A hotel kitchen with marble tiles, a coffee machine, a refrigerator, and a counter with various items.

17. Baymont by Wyndham

11.7 km from Windsor Ski Lift

Brian

AED 288

AED 321 total

includes taxes & fees

8 Nov - 9 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a covered seating area.

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 dining table set with plates, cutlery, and glasses, with two leather stools and a window with blinds in the background.

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

18. Palm Cottages

11.6 km from Windsor Ski Lift

Eric

AED 701

AED 781 total

includes taxes & fees

2 Nov - 3 Nov

A spacious kitchen with a central island, bar stools, and a fireplace.

A cozy living room with a sofa, a woven hanging chair, a round pouf, and a large abstract painting.

A modern kitchen with a large island, white cabinetry, and a view of the city.

A spacious dining area with a long wooden table and cushioned chairs, a bookshelf, and a fireplace.

19. Paschal Winery

19.6 km from Windsor Ski Lift

Christine

AED 436

AED 1,478 total

includes taxes & fees

8 Nov - 9 Nov

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 modern bedroom with a large bed, bedside tables, 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.

20. Grandview of Ashland

13 km from Windsor Ski Lift

Sonja

AED 750

AED 1,504 total

includes taxes & fees

14 Oct - 15 Oct

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Compare popular hotels close to Windsor Ski Lift

Property	Property class	Guest rating
Callahan's Mountain Lodge	8.8 Excellent 1,131 reviews	View
Timbers INN and Suites	8.8 Excellent 1,000 reviews	View
Best Western Windsor Inn	9.0 Wonderful 1,000 reviews	View
Prospero's Flagship Inn	8.4 Very good 1,482 reviews	View
Comfort Inn & Suites Ashland	9.0 Wonderful 1,037 reviews	View

Top Windsor Ski Lift Hotel Reviews

Comfort Inn & Suites Ashland

10/10 Excellent

"Cortland was very helpful. Good location. Beds good, little bit old property. Would stay again"

Plaza Inn & Suites at Ashland Creek

10/10 Excellent

"Nice place close to town. Excellent breakfast."

Ashland Springs Hotel

8/10 Good

"The room was fine, older but updated. The only thing we would skip is the $5 breakfast voucher, would have rather gone out for breakfast."

Holiday Inn Express & Suites Ashland by IHG

8/10 Good

"Great option not too far from downtown Ashland. Clean and new, decent breakfast, oool and hot tub"

Winchester Inn

8/10 Good

"This inn is very sweet - and so well located. The room was spacious enough and the cooked breakfast option was a total highlight. The rooms, I said"

Baymont by Wyndham

10/10 Excellent

"I've stayed here many times now and always a great experience."

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."

Country Willows Inn and Estate

10/10 Excellent

"Beautiful property with gardens and a heated pool. Great staff, breakfast was inventive and quite tasty. Is 10 minutes from town but easy to drive and no real parking issues even at play times. We will be back next year"

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 223

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Star rating

Guest rating

Our top choices for Windsor Ski Lift hotels

1. Callahan's Mountain Lodge

2. Timbers INN and Suites

3. Best Western Windsor Inn

4. Prospero's Flagship Inn

5. Comfort Inn & Suites Ashland

6. Holiday Inn Express & Suites Ashland by IHG

7. Ashland Commons Hostel

8. Ashland Hills Hotel & Suites

9. The Peerless Hotel by WanderLodges

10. Plaza Inn & Suites at Ashland Creek

11. Country Willows Inn and Estate

12. Winchester Inn

13. Arden Forest Inn

14. Lithia Springs Resort

15. Ashland Motel - Oregon

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

17. Baymont by Wyndham

18. Palm Cottages

19. Paschal Winery

20. Grandview of Ashland

Compare popular hotels close to Windsor Ski Lift

Top Windsor Ski Lift Hotel Reviews

Comfort Inn & Suites Ashland

Plaza Inn & Suites at Ashland Creek

Ashland Springs Hotel

Holiday Inn Express & Suites Ashland by IHG

Winchester Inn

Baymont by Wyndham

Ashland Motel - Oregon

Palm Cottages

Country Willows Inn and Estate

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