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.

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

A hotel sign with the name "Straford Inn" and a stone pillar.

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

1. Stratford Inn

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

David

SAR 351

SAR 391 total

includes taxes & fees

1 Nov - 2 Nov

A Holiday Inn Express hotel with a two-story structure, a parking lot, and a landscaped area with shrubs and a tall tree.

A hotel lobby with a reception desk, seating area, and a large window.

A buffet with various food items in metal containers, including omelets and other dishes.

A modern hotel room with a dark wood wardrobe, a black refrigerator, a microwave, a sink, and a chair.

2. Holiday Inn Express & Suites Ashland by IHG

11.6 km from Windsor Ski Lift

Lorenzo

SAR 372

SAR 414 total

includes taxes & fees

23 Nov - 24 Nov

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

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

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

Ross

SAR 422

SAR 471 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.

4. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Nicholas

SAR 368

SAR 448 total

includes taxes & fees

19 Nov - 20 Nov

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 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.

5. Comfort Inn & Suites Ashland

15.9 km from Windsor Ski Lift

Bill

SAR 386

SAR 392 total

includes taxes & fees

24 Nov - 25 Nov

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

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.

6. Callahan's Mountain Lodge

8.8 km from Windsor Ski Lift

Meena

SAR 378

SAR 440 total

includes taxes & fees

14 Nov - 15 Nov

A swimming pool with a clear view of the poolside area, including lounge chairs and a covered seating area.

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.

A hotel room with a large bed, a desk, and a window with curtains.

7. Timbers INN and Suites

11.3 km from Windsor Ski Lift

Sarah

SAR 234

SAR 261 total

includes taxes & fees

27 Oct - 28 Oct

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.

8. Prospero's Flagship Inn

11.4 km from Windsor Ski Lift

Mary

SAR 227

SAR 254 total

includes taxes & fees

27 Oct - 28 Oct

A large, two-story house with a wrap-around porch and a steeply pitched roof.

A living room with a fireplace, two armchairs, a sofa, and a TV mounted on the wall.

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

9. Winchester Inn

Historic Downtown District, 12.3 km from Windsor Ski Lift

Ellen

SAR 501

SAR 619 total

includes taxes & fees

9 Nov - 10 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.

10. The Peerless Hotel by WanderLodges

Historic Railroad District, 12.6 km from Windsor Ski Lift

Lindsay

SAR 309

SAR 550 total

includes taxes & fees

28 Oct - 29 Oct

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

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

11. Plaza Inn & Suites at Ashland Creek

12.9 km from Windsor Ski Lift

Bill

SAR 436

SAR 486 total

includes taxes & fees

1 Nov - 2 Nov

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

A well-lit room with a sofa, chairs, and a coffee table. There are bookshelves filled with books and decorative items.

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.

12. Lithia Springs Resort

15.4 km from Windsor Ski Lift

Steven

SAR 351

SAR 432 total

includes taxes & fees

16 Nov - 17 Nov

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

13. Country Willows Inn and Estate

10 km from Windsor Ski Lift

Diane

SAR 727

SAR 738 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 man sitting at a table with a notebook, writing. The table has a cup, a small plant, and some pumpkins on it.

14. Ashland Commons Hostel

12.9 km from Windsor Ski Lift

Sam

SAR 248

SAR 277 total

includes taxes & fees

26 Nov - 27 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

Duff

SAR 351

SAR 450 total

includes taxes & fees

15 Nov - 16 Nov

A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

A living room with a glass coffee table, a television, a chair, and a view of mountains through the window.

A spacious living room with a large TV, comfortable seating, and a chandelier.

A kitchen with white cabinets, a microwave, and a window with curtains.

16. Barclay Klum House by WanderLodges

12.2 km from Windsor Ski Lift

Melissa

SAR 429

SAR 960 total

includes taxes & fees

29 Oct - 30 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

Thomas

SAR 513

SAR 573 total

includes taxes & fees

2 Nov - 3 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 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 compact kitchen with white cabinets, a dining table with chairs, a refrigerator, and a built-in oven.

18. Hanna's House by WanderLodges

Historic Railroad District, 12.3 km from Windsor Ski Lift

Robert

SAR 422

SAR 760 total

includes taxes & fees

2 Nov - 3 Nov

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.

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

Historic Downtown District, 12.8 km from Windsor Ski Lift

Thomas

SAR 372

SAR 414 total

includes taxes & fees

26 Nov - 27 Nov

A modern kitchen with wooden beams, a dining area with a rug, and a large island.

A two-story house with a blue exterior, a red roof, and a front porch.

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.

20. The Mountain Ave House by WanderLodges

12.3 km from Windsor Ski Lift

Joyce

SAR 652

SAR 1,271 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
Stratford Inn	9.4 Exceptional 1,800 reviews	View
Holiday Inn Express & Suites Ashland by IHG	9.4 Exceptional 1,008 reviews	View
Best Western Windsor Inn	9.0 Wonderful 1,005 reviews	View
Ashland Hills Hotel & Suites	8.8 Excellent 1,567 reviews	View
Comfort Inn & Suites Ashland	9.0 Wonderful 1,058 reviews	View

Top Windsor Ski Lift Hotel Reviews

Plaza Inn & Suites at Ashland Creek

10/10 Excellent

"Super cute, comfy, and cozy location. I love the 2 minute trail to downtown."

Callahan's Mountain Lodge

10/10 Excellent

"We stayed for our 13th wedding anniversary. We found our room to be so cozy! We loved the jetted tub, the fireplace, the semi-private deck and the comfy bed. We will definitely be back."

Best Western Windsor Inn

10/10 Excellent

"Friendly staff, location"

Baymont by Wyndham

8/10 Good

"It was fine for a quick getaway. Nothing amazing but the bed was comfy and it was clean so I think 4 stars fits."

Ashland Hills Hotel & Suites

10/10 Excellent

"Places was super clean, staff was nice, restaurant in hotel closes early around 9pm"

Ashland Springs Hotel

10/10 Excellent

"great meal there at the Larks restaurant, too. Staff is great. Room comfortable although some furniture is old, but its a classic hotel in a great location. Highly recommend."

Stratford Inn

10/10 Excellent

"Staff was friendly and helpful."

Cedarwood Inn of Ashland

10/10 Excellent

"Dadar is very friendly working the front desk! We were able to get a deal on the room, and it was very clean. Breakfast was good and the space was clean too. Would return."

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."

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 SAR 254

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Be picky

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Our top choices for Windsor Ski Lift hotels

1. Stratford Inn

2. Holiday Inn Express & Suites Ashland by IHG

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. Winchester Inn

10. The Peerless Hotel by WanderLodges

11. Plaza Inn & Suites at Ashland Creek

12. Lithia Springs Resort

13. Country Willows Inn and Estate

14. Ashland Commons Hostel

15. Ashland Springs Hotel

16. Barclay Klum House by WanderLodges

17. Arden Forest Inn

18. Hanna's House by WanderLodges

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

20. The Mountain Ave House by WanderLodges

Compare popular hotels close to Windsor Ski Lift

Top Windsor Ski Lift Hotel Reviews

Plaza Inn & Suites at Ashland Creek

Callahan's Mountain Lodge

Best Western Windsor Inn

Baymont by Wyndham

Ashland Hills Hotel & Suites

Ashland Springs Hotel

Stratford Inn

Cedarwood Inn of Ashland

Ashland Motel - Oregon

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