⭐ Top 10 Hotels Near Windsor Ski Lift for 2026

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Our top choices for Windsor Ski Lift hotels

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

A hotel room with a bed, a desk with a TV, a chair, and a microwave.

1. Comfort Inn & Suites Ashland

15.9 km from Windsor Ski Lift

Mary Anna

S$146

includes taxes & fees

25 Oct - 26 Oct

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 lobby with leather sofas, a rug, and lamps.

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

2. Stratford Inn

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

David

S$159

includes taxes & fees

18 Oct - 19 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 spacious living room with a high ceiling, large windows, and a mix of seating arrangements including a sofa and chairs.

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.

3. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Krishnaharsha

S$154

includes taxes & fees

1 Nov - 2 Nov

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

4. Best Western Windsor Inn

11.9 km from Windsor Ski Lift

Deborah

S$152

includes taxes & fees

31 Oct - 1 Nov

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.

A hotel room with a large bed, a separate bathroom with a bathtub, a window with curtains, and a view of the outdoors.

5. Callahan's Mountain Lodge

8.8 km from Windsor Ski Lift

Meena

S$172

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 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.

A wooden deck with white lounge chairs and a table, surrounded by a wooden fence and trees.

A hotel entrance with a sign, a pedestrian crossing sign, and a road with trees.

6. Prospero's Flagship Inn

11.4 km from Windsor Ski Lift

Karla

S$83

includes taxes & fees

19 Oct - 20 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.

7. Ashland Commons Hostel

12.9 km from Windsor Ski Lift

Sam

S$94

includes taxes & fees

25 Oct - 26 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 hotel bathroom with a wooden door, a sink with a mirror, a towel rack, a coffee maker, and a black refrigerator.

A hotel room with a blue sofa, a black coffee table, a bed with white linens, and a large window with curtains.

8. Holiday Inn Express & Suites Ashland by IHG

11.6 km from Windsor Ski Lift

Lorenzo

S$143

includes taxes & fees

12 Nov - 13 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.

9. Timbers INN and Suites

11.3 km from Windsor Ski Lift

Evangelina

S$90

includes taxes & fees

3 Nov - 4 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 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.

10. Lithia Springs Resort

15.4 km from Windsor Ski Lift

Steven

S$148

includes taxes & fees

1 Nov - 2 Nov

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

A bar with multiple shelves of bottles, tables, and chairs arranged for patrons.

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.

11. Winchester Inn

Historic Downtown District, 12.3 km from Windsor Ski Lift

Ellen

S$210

includes taxes & fees

26 Oct - 27 Oct

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 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.

12. Plaza Inn & Suites at Ashland Creek

12.9 km from Windsor Ski Lift

Stephen

S$166

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 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.

13. The Peerless Hotel by WanderLodges

Historic Railroad District, 12.6 km from Windsor Ski Lift

Jaye

S$234

includes taxes & fees

15 Nov - 16 Nov

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 garden with a pond, stone walls, and various plants.

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

14. Country Willows Inn and Estate

10 km from Windsor Ski Lift

raymon

S$253

includes taxes & fees

1 Nov - 2 Nov

An outdoor patio area with tables and chairs, string lights, and potted plants.

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.

A grand lobby with a high ceiling, large windows, and a central staircase.

15. Ashland Springs Hotel

Historic Downtown District, 12.4 km from Windsor Ski Lift

Susan

S$154

includes taxes & fees

8 Nov - 9 Nov

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

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

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

A garden with a red pergola, a stone fountain, and purple flowers.

16. Arden Forest Inn

13.3 km from Windsor Ski Lift

Thomas

S$217

includes taxes & fees

14 Nov - 15 Nov

A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

A single-story house with a covered porch, a small garden with rocks and a tree, and a mailbox.

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.

17. Hanna's House by WanderLodges

Historic Railroad District, 12.3 km from Windsor Ski Lift

Robert

S$253

includes taxes & fees

19 Oct - 20 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 room with four armchairs, a bench, and a table with a lamp. There are large windows with a view of greenery outside.

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

Historic Downtown District, 12.8 km from Windsor Ski Lift

Stephen

S$178

includes taxes & fees

8 Nov - 9 Nov

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

A two-story house with a prominent staircase leading to the entrance.

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.

19. Barclay Klum House by WanderLodges

12.2 km from Windsor Ski Lift

Melissa

S$329

includes taxes & fees

18 Oct - 19 Oct

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

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

20. Palm Cottages

11.6 km from Windsor Ski Lift

Eric

S$288

includes taxes & fees

16 Oct - 17 Oct

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Compare popular hotels close to Windsor Ski Lift

Property	Property class	Guest rating
Comfort Inn & Suites Ashland	9.0 Wonderful 1,044 reviews	View
Stratford Inn	9.4 Exceptional 1,793 reviews	View
Ashland Hills Hotel & Suites	8.8 Excellent 1,550 reviews	View
Best Western Windsor Inn	9.0 Wonderful 1,000 reviews	View
Callahan's Mountain Lodge	8.8 Excellent 1,129 reviews	View

Top Windsor Ski Lift Hotel Reviews

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

8/10 Good

"The room was clean and the bed was comfortable. However, the pillows are in dire need for an upgrade. And the bathroom could use a renovation. The hotel is very convenient for attending the theater at the Shakespeare Festival, and is also a short walk to all of the area restaurants. In addition, it was very convenient to have two free, electric car chargers in the parking lot."

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."

Relax Inn At Ashland

8/10 Good

"Great little room that was very clean and had access to a coffee stand, gas station, and several spots for food. The hotel had friendly staff, decent parking, and affordable prices. It was perfect for a stay to visit Ashland, Medford, and Crater Lake. Overall a great stay."

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."

Timbers INN and Suites

10/10 Excellent

"Our room was very clean and comfortable and our staff interaction was great. We’ll definitely stay here again when we come to Ashland."

Stratford Inn

10/10 Excellent

"An easy walk to the theaters and stores. If we needed anything, Safeway was across the street. Well maintained older property, clean and comfortable. The staff was helpful, courteous and informative. We plan on returning."

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"

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."

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 303 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.

Hotels near Windsor Ski Lift

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Our top choices for Windsor Ski Lift hotels

1. Comfort Inn & Suites Ashland

2. Stratford Inn

3. Ashland Hills Hotel & Suites

4. Best Western Windsor Inn

5. Callahan's Mountain Lodge

6. Prospero's Flagship Inn

7. Ashland Commons Hostel

8. Holiday Inn Express & Suites Ashland by IHG

9. Timbers INN and Suites

10. Lithia Springs Resort

11. Winchester Inn

12. Plaza Inn & Suites at Ashland Creek

13. The Peerless Hotel by WanderLodges

14. Country Willows Inn and Estate

15. Ashland Springs Hotel

16. Arden Forest Inn

17. Hanna's House by WanderLodges

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

19. Barclay Klum House by WanderLodges

20. Palm Cottages

Compare popular hotels close to Windsor Ski Lift

Top Windsor Ski Lift Hotel Reviews

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

Ashland Motel - Oregon

Relax Inn At Ashland

Country Willows Inn and Estate

Timbers INN and Suites

Stratford Inn

Winchester Inn

Baymont by Wyndham

Ashland Springs Hotel

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