Top 10 Hotels Near Windsor Ski Lift in Ashland for 2026

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Our top choices for Windsor Ski Lift hotels

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

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.

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

1. Holiday Inn Express & Suites Ashland by IHG

11.6 km from Windsor Ski Lift

Hardeep

RM465

RM519 total

includes taxes & fees

28 Sept - 29 Sept

A wooden balcony with a view of a forested area.

An outdoor dining area with round tables, white chairs, and umbrellas.

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

2. Callahan's Mountain Lodge

8.8 km from Windsor Ski Lift

Michelle

RM491

RM559 total

includes taxes & fees

14 Sept - 15 Sept

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

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

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

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

3. Country Willows Inn and Estate

10 km from Windsor Ski Lift

raymon

RM1,024

RM1,040 total

includes taxes & fees

6 Sept - 7 Sept

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.

4. Best Western Windsor Inn

11.9 km from Windsor Ski Lift

Dennis

RM455

RM507 total

includes taxes & fees

21 Sept - 22 Sept

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

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

5. Barclay Klum House by WanderLodges

12.2 km from Windsor Ski Lift

Melissa

RM564

RM1,148 total

includes taxes & fees

7 Sept - 8 Sept

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

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

A modern hotel lobby with a leather sofa, a coffee table, a patterned rug, a reception desk, and a wall-mounted snack station.

A Zen garden with a statue, surrounded by various plants and rocks.

6. Timbers INN and Suites

11.3 km from Windsor Ski Lift

Robin

RM309

RM345 total

includes taxes & fees

7 Sept - 8 Sept

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 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.

7. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Krishnaharsha

RM506

RM605 total

includes taxes & fees

7 Sept - 8 Sept

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

8. Palm Cottages

11.6 km from Windsor Ski Lift

David

RM813

RM906 total

includes taxes & fees

6 Sept - 7 Sept

A sign for Prospero's Flagship Inn with a star emblem and a pedestrian crossing sign nearby.

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.

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.

9. Prospero's Flagship Inn

11.4 km from Windsor Ski Lift

Denise

RM251

RM280 total

includes taxes & fees

7 Sept - 8 Sept

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 lobby with a reception desk, blue upholstered sofas, a patterned carpet, and a decorative wall.

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

10. Comfort Inn & Suites Ashland

15.9 km from Windsor Ski Lift

armida

RM440

RM447 total

includes taxes & fees

28 Sept - 29 Sept

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 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.

11. Hanna's House by WanderLodges

Historic Railroad District, 12.3 km from Windsor Ski Lift

David

RM688

RM1,078 total

includes taxes & fees

10 Sept - 11 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 hotel kitchen with marble tiles, a coffee machine, a refrigerator, and a counter with various items.

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

12. Baymont by Wyndham

11.7 km from Windsor Ski Lift

Virgilio

RM364

RM406 total

includes taxes & fees

4 Oct - 5 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.

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

Historic Downtown District, 12.8 km from Windsor Ski Lift

Dawn

RM683

RM762 total

includes taxes & fees

14 Sept - 15 Sept

A bed with a striped blanket, a pillow, and a view of a cityscape through a window.

A motel with a prominent sign advertising free HBO, cable TV, phone, and parking.

A breakfast setup with a stainless steel water bottle, stacked plates, and baskets containing bread, utensils, and fruits like bananas, oranges, and apples.

A compact kitchen with a window, a refrigerator, and a sink.

14. Relax Inn At Ashland

11.7 km from Windsor Ski Lift

Duane

RM275

RM307 total

includes taxes & fees

13 Sept - 14 Sept

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 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

Don

RM318

RM355 total

includes taxes & fees

7 Sept - 8 Sept

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Compare popular hotels close to Windsor Ski Lift

Property	Property class	Guest rating
Holiday Inn Express & Suites Ashland by IHG	9.2 Wonderful 1,006 reviews	View
Callahan's Mountain Lodge	8.8 Excellent 1,146 reviews	View
Country Willows Inn and Estate	9.8 Exceptional 41 reviews	View
Best Western Windsor Inn	9.0 Wonderful 1,004 reviews	View
Barclay Klum House by WanderLodges	10.0 Exceptional 9 reviews	View

Top Windsor Ski Lift Hotel Reviews

Winchester Inn

10/10 Excellent

"Our stay at the Winchester Inn was very pleasant and enjoyable. The complimentary made to order breakfast was delicious, and the room was very comfortable and quiet. The location was very convenient and walkable to downtown's many excellent restaurants and the Shakespeare Festival. Would definitely stay there again."

Comfort Inn & Suites Ashland

10/10 Excellent

"The location of this property is near I-5 on the northern part of Ashland. Although the property is next to the freeway our room was very quiet. The drive to the Oregon Shakespeare Festival is about 10 minutes. We had a room with one king,size bed. The room was nicely furnished with two comfortable chairs for reading or watching TV. In addition there was a very decent desk chair at the desk. Breakfast was in a generous size room and was among the best in a roadside motel. Will definitely stay again."

Palm Cottages

10/10 Excellent

"Such a charming property! Staff was very helpful, property very clean and cute. There were several deer on the property just roaming around. Our cottage was adorable! Comfortable bed as well. Highly recommend!"

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

10/10 Excellent

"Friendly staff and easy access to theaters and restaurants."

Stratford Inn

10/10 Excellent

"Room was clean and comfortable. Staff available, helpful and friendly. Great complimentary breakfast."

Ashland Hills Hotel & Suites

10/10 Excellent

"Amazing staff!"

Prospero's Flagship Inn

10/10 Excellent

"Bathroom door squeaked loudly. Clean, comfortable rooms. Good price. So-so breakfast. Conveniently located near Case Coffee, Sammich, Morning Glory Cafe, and a 7 Eleven. Easy access to downtown Ashland’s shopping and dining and the Oregon Shakespeare Festival."

Best Western Windsor Inn

10/10 Excellent

"Nice play for. An overnight stay. No nonsense. Good room sizes. Breakfast was adequate with eggs and bacon. Things were clean and staff very friendly."

Plaza Inn & Suites at Ashland Creek

10/10 Excellent

"The hotel was clean and most of the staff very helpful. We were located in a small, remote section of the hotel so umbrellas in the rooms would have been helpful to get to the main building where breakfast, ice & other amenities are located. At check out I asked for a receipt but was told that, since I booked through a third party, it would come from them. On this trip I booked 4 hotels through Hotels.com and all but this one provided a receipt. Seemed very unhelpful to me. If you are normally a walker it is an easy walk to the shops and many restaurants."

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 entertainment choices in this family-friendly 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 acclaimed theatre scene.

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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 317 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 Lithia Artisans Market and Tashi Choling Buddhist Center.

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. Holiday Inn Express & Suites Ashland by IHG

2. Callahan's Mountain Lodge

3. Country Willows Inn and Estate

4. Best Western Windsor Inn

5. Barclay Klum House by WanderLodges

6. Timbers INN and Suites

7. Ashland Hills Hotel & Suites

8. Palm Cottages

9. Prospero's Flagship Inn

10. Comfort Inn & Suites Ashland

11. Hanna's House by WanderLodges

12. Baymont by Wyndham

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

14. Relax Inn At Ashland

15. Ashland Motel - Oregon

Compare popular hotels close to Windsor Ski Lift

Top Windsor Ski Lift Hotel Reviews

Winchester Inn

Comfort Inn & Suites Ashland

Palm Cottages

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

Stratford Inn

Ashland Hills Hotel & Suites

Prospero's Flagship Inn

Best Western Windsor Inn

Plaza Inn & Suites at Ashland Creek

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