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

AED 289

AED 323 total

includes taxes & fees

1 Nov - 2 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.

2. Callahan's Mountain Lodge

8.8 km from Windsor Ski Lift

Karen

AED 463

AED 525 total

includes taxes & fees

28 Oct - 29 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 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.

3. Timbers INN and Suites

11.3 km from Windsor Ski Lift

Robin

AED 215

AED 240 total

includes taxes & fees

18 Oct - 19 Oct

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

A restaurant with high ceilings, large windows, and a mix of seating arrangements including tables and booths.

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

Dennis

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 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.

5. Prospero's Flagship Inn

11.4 km from Windsor Ski Lift

Jenny

AED 248

AED 276 total

includes taxes & fees

1 Nov - 2 Nov

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 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.

6. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Krishnaharsha

AED 417

AED 502 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

7. Holiday Inn Express & Suites Ashland by IHG

11.6 km from Windsor Ski Lift

Adam

AED 389

AED 434 total

includes taxes & fees

26 Oct - 27 Oct

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

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.

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

8. Comfort Inn & Suites Ashland

15.9 km from Windsor Ski Lift

Christina

AED 413

AED 419 total

includes taxes & fees

7 Oct - 8 Oct

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.

9. Ashland Commons Hostel

12.9 km from Windsor Ski Lift

Brenda

AED 245

AED 274 total

includes taxes & fees

4 Oct - 5 Oct

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

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

10. The Peerless Hotel by WanderLodges

Historic Railroad District, 12.6 km from Windsor Ski Lift

Jaye

AED 499

AED 757 total

includes taxes & fees

6 Oct - 7 Oct

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

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

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.

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

12. Grandview of Ashland

13 km from Windsor Ski Lift

Sonja

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.

13. 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 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.

14. Lithia Springs Resort

15.4 km from Windsor Ski Lift

Steven

AED 293

AED 371 total

includes taxes & fees

1 Nov - 2 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.

15. Ashland Springs Hotel

Historic Downtown District, 12.4 km from Windsor Ski Lift

Susan

AED 312

AED 405 total

includes taxes & fees

1 Nov - 2 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 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.

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

Historic Downtown District, 12.8 km from Windsor Ski Lift

Dawn

AED 474

AED 528 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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.

17. Palm Cottages

11.6 km from Windsor Ski Lift

Eric

AED 701

AED 781 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 modern living room with a brown leather sofa, a black coffee table, and a kitchen area with wooden cabinets and a marble backsplash.

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

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

18. Baymont by Wyndham

11.7 km from Windsor Ski Lift

Brian

AED 311

AED 346 total

includes taxes & fees

4 Oct - 5 Oct

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 pathway leading to a building with a decorative archway, surrounded by flowering trees and a well-maintained lawn.

19. Ashland Motel - Oregon

11.5 km from Windsor Ski Lift

AED 285

AED 318 total

includes taxes & fees

18 Oct - 19 Oct

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

A modern bathroom with a sink, mirror, and toiletries.

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.

20. Paschal Winery

19.6 km from Windsor Ski Lift

Christine

AED 482

AED 1,524 total

includes taxes & fees

7 Oct - 8 Oct

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Compare popular hotels close to Windsor Ski Lift

Property	Property class	Guest rating
Stratford Inn	9.4 Exceptional 1,782 reviews	View
Callahan's Mountain Lodge	8.8 Excellent 1,137 reviews	View
Timbers INN and Suites	8.8 Excellent 1,008 reviews	View
Best Western Windsor Inn	9.0 Wonderful 1,001 reviews	View
Prospero's Flagship Inn	8.4 Very good 1,479 reviews	View

Top Windsor Ski Lift Hotel Reviews

Ashland Hills Hotel & Suites

8/10 Good

"Overall we enjoyed the stay. Staff was friendly and bed was comfortable. Breakfast was not included which would have been nice."

Relax Inn At Ashland

10/10 Excellent

"Check in was quick and easy. Desk concierge was friendly and efficient."

Comfort Inn & Suites Ashland

10/10 Excellent

"Our room was spacious. The breakfast choices were good."

Plaza Inn & Suites at Ashland Creek

8/10 Good

"If you are attending an Oregon Shakespeare Festival play, this property is beautifully located about a 10-minute walk from the festival grounds, various restaurants, and Lithia Park. My assigned room wasn't one of the best rooms as it had no balcony or view of the river, but it worked very well for me as I was walking to and from the festival grounds and my room was on the ground floor near an entrance to the play route. Covered parking was nice to have. Breakfast was very good, but always the same and served in a very nice room with access to a balcony overlooking the river so nice for summer or early fall. Tiny tubes of shampoo and other amenities worked fine if you were only staying a day but luckily were replenished daily."

Ashland Motel - Oregon

10/10 Excellent

"An excellent family-run motel. The rooms are on the small side, but they are immaculately clean. I highly recommend if you are looking for a budget hotel near downtown Ashland."

Cedarwood Inn of Ashland

10/10 Excellent

"Good location, good value."

Baymont by Wyndham

8/10 Good

"Had a problem with the TV they replaced it the same day."

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."

Callahan's Mountain Lodge

10/10 Excellent

"The bartender/server named Sunshine made our time so much more enjoyable! She was delightful and helpful in many ways."

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 240

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. Stratford Inn

2. Callahan's Mountain Lodge

3. Timbers INN and Suites

4. Best Western Windsor Inn

5. Prospero's Flagship Inn

6. Ashland Hills Hotel & Suites

7. Holiday Inn Express & Suites Ashland by IHG

8. Comfort Inn & Suites Ashland

9. Ashland Commons Hostel

10. The Peerless Hotel by WanderLodges

11. Plaza Inn & Suites at Ashland Creek

12. Grandview of Ashland

13. Country Willows Inn and Estate

14. Lithia Springs Resort

15. Ashland Springs Hotel

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

17. Palm Cottages

18. Baymont by Wyndham

19. Ashland Motel - Oregon

20. Paschal Winery

Compare popular hotels close to Windsor Ski Lift

Top Windsor Ski Lift Hotel Reviews

Ashland Hills Hotel & Suites

Relax Inn At Ashland

Comfort Inn & Suites Ashland

Plaza Inn & Suites at Ashland Creek

Ashland Motel - Oregon

Cedarwood Inn of Ashland

Baymont by Wyndham

Palm Cottages

Callahan's Mountain Lodge

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