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

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

A lobby with leather sofas, a rug, and lamps.

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

HK$736

HK$820 total

includes taxes & fees

12 Oct - 13 Oct

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.

2. Holiday Inn Express & Suites Ashland by IHG

11.6 km from Windsor Ski Lift

Hardeep

HK$871

HK$971 total

includes taxes & fees

21 Oct - 22 Oct

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.

A wooden balcony with a view of a forested area.

3. Callahan's Mountain Lodge

8.8 km from Windsor Ski Lift

Michelle

HK$1,052

HK$1,185 total

includes taxes & fees

1 Oct - 2 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 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.

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

4. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Krishnaharsha

HK$905

HK$1,088 total

includes taxes & fees

27 Sept - 28 Sept

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.

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

5. Best Western Windsor Inn

11.9 km from Windsor Ski Lift

Dennis

HK$883

HK$984 total

includes taxes & fees

28 Sept - 29 Sept

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

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.

A hotel room with a gray sofa, a small wooden table, a framed picture on the wall, a floor lamp, and a carpeted floor.

6. Comfort Inn & Suites Ashland

15.9 km from Windsor Ski Lift

Amber

HK$876

HK$889 total

includes taxes & fees

28 Sept - 29 Sept

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.

7. Prospero's Flagship Inn

11.4 km from Windsor Ski Lift

Denise

HK$558

HK$622 total

includes taxes & fees

27 Sept - 28 Sept

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

8. Plaza Inn & Suites at Ashland Creek

12.9 km from Windsor Ski Lift

Alan

HK$1,264

HK$1,409 total

includes taxes & fees

27 Sept - 28 Sept

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$1,138

HK$1,312 total

includes taxes & fees

5 Oct - 6 Oct

A backyard with a swimming pool, patio furniture, a small pond, and a wooden cabin.

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

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

A gazebo with a wooden roof and white curtains, surrounded by lush greenery and autumn-colored trees.

10. Country Willows Inn and Estate

10 km from Windsor Ski Lift

raymon

HK$2,125

HK$2,156 total

includes taxes & fees

23 Sept - 24 Sept

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

A room with a brick wall, a wooden dresser, a chair, and a bed.

11. The Peerless Hotel by WanderLodges

Historic Railroad District, 12.6 km from Windsor Ski Lift

Jaye

HK$1,202

HK$1,769 total

includes taxes & fees

27 Sept - 28 Sept

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.

12. Grandview of Ashland

13 km from Windsor Ski Lift

Sonja

HK$2,111

HK$3,728 total

includes taxes & fees

4 Oct - 5 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 grand chandelier, a fireplace, and a large window offering a view of the outdoors.

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$1,408

HK$1,695 total

includes taxes & fees

19 Oct - 20 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 bedroom with a bed, a nightstand, a lamp, a chair, a potted plant, and a door.

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

14. Arden Forest Inn

13.3 km from Windsor Ski Lift

Thomas

HK$1,589

HK$1,771 total

includes taxes & fees

14 Oct - 15 Oct

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

A well-maintained garden with a variety of plants and a wooden fence.

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

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.

15. Palm Cottages

11.6 km from Windsor Ski Lift

Eric

HK$1,576

HK$1,758 total

includes taxes & fees

23 Sept - 24 Sept

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.

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

Historic Downtown District, 12.8 km from Windsor Ski Lift

Dawn

HK$1,091

HK$1,216 total

includes taxes & fees

18 Oct - 19 Oct

A two-story house with a porch, surrounded by a well-maintained garden with various flowers and shrubs.

A garden pathway leading to a building with a pergola and hanging flower baskets.

A grand staircase with wooden balusters and a carpeted landing.

A spacious dining area with a wooden table and chairs, large windows with a view of the outdoors, and a chandelier.

17. Abigail’s Bed & Breakfast Inn

Skidmore Academy Historic District, 13.4 km from Windsor Ski Lift

Kim

HK$2,354

HK$2,624 total

includes taxes & fees

23 Sept - 24 Sept

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

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

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.

18. Paschal Winery

19.6 km from Windsor Ski Lift

Christine

HK$1,094

HK$3,323 total

includes taxes & fees

27 Sept - 28 Sept

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 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.

19. Baymont by Wyndham

11.7 km from Windsor Ski Lift

Virgilio

HK$706

HK$787 total

includes taxes & fees

4 Oct - 5 Oct

A hotel room with a desk, laptop, two beds, and a round mirror.

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

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.

20. Ashland Motel - Oregon

11.5 km from Windsor Ski Lift

Madrik A.

HK$609

HK$679 total

includes taxes & fees

27 Sept - 28 Sept

View all properties

Compare popular hotels close to Windsor Ski Lift

Property	Property class	Guest rating
Stratford Inn	9.4 Exceptional 1,795 reviews	View
Holiday Inn Express & Suites Ashland by IHG	9.2 Wonderful 1,001 reviews	View
Callahan's Mountain Lodge	8.8 Excellent 1,142 reviews	View
Ashland Hills Hotel & Suites	8.8 Excellent 1,538 reviews	View
Best Western Windsor Inn	9.0 Wonderful 1,005 reviews	View

Top Windsor Ski Lift Hotel Reviews

Callahan's Mountain Lodge

8/10 Good

"We had a lovely stay. Our room was spacious, but a little worn. It was clean enough, but not spotless. A very friendly and helpful staff and really excellent food in the restaurant. The price is good and the location is beautiful. We stayed there for our trip to see the OSF festival as the prices now is Ashland are very high. Thank you"

Holiday Inn Express & Suites Ashland by IHG

10/10 Excellent

"Everything was to our satisfaction, noise level, cleanliness, friendly staff. Quite a bit of travelers at this time also."

Timbers INN and Suites

10/10 Excellent

"Easy walk to great food! Try falafel republic! Yum! Clean! Good A/C. Spacious for a family of 5"

Ashland Hills Hotel & Suites

10/10 Excellent

"Room was overlooking parking lot but was quiet.Nice part of town."

Relax Inn At Ashland

10/10 Excellent

"Very well-cared for facility. Clean, comfortable and quiet."

Plaza Inn & Suites at Ashland Creek

10/10 Excellent

"Charming hotel. Great value especially when you factor in the free Tesla charging and the excellent buffet breakfast."

Winchester Inn

10/10 Excellent

"The property is very charming, and comfortable with beautiful gardens and outdoor spaces. The breakfast choices were delicious and dinner was also exceptional. Staff is very warm, friendly and helpful. I recommend highly."

Baymont by Wyndham

10/10 Excellent

"It looked like there hotel was being brought up to date with new TVs and recent painting inside my room. The walks seemed a bit thin as I could hear a baby cry off and on for several hours in the afternoon. I couldn’t figure out how to get the local channels either the remote so just used my iPad Good WiFi"

Cedarwood Inn of Ashland

10/10 Excellent

"Clean and safe. Great value."

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 311 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. Stratford Inn

2. Holiday Inn Express & Suites Ashland by IHG

3. Callahan's Mountain Lodge

4. Ashland Hills Hotel & Suites

5. Best Western Windsor Inn

6. Comfort Inn & Suites Ashland

7. Prospero's Flagship Inn

8. Plaza Inn & Suites at Ashland Creek

9. Lithia Springs Resort

10. Country Willows Inn and Estate

11. The Peerless Hotel by WanderLodges

12. Grandview of Ashland

13. Ashland Springs Hotel

14. Arden Forest Inn

15. Palm Cottages

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

17. Abigail’s Bed & Breakfast Inn

18. Paschal Winery

19. Baymont by Wyndham

20. Ashland Motel - Oregon

Compare popular hotels close to Windsor Ski Lift

Top Windsor Ski Lift Hotel Reviews

Callahan's Mountain Lodge

Holiday Inn Express & Suites Ashland by IHG

Timbers INN and Suites

Ashland Hills Hotel & Suites

Relax Inn At Ashland

Plaza Inn & Suites at Ashland Creek

Winchester Inn

Baymont by Wyndham

Cedarwood Inn of Ashland

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