Top 10 Hotels Near 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.

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

RM381

RM425 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.

2. Comfort Inn & Suites Ashland

15.9 km from Windsor Ski Lift

Bill

RM458

RM465 total

includes taxes & fees

22 Nov - 23 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 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.

3. Holiday Inn Express & Suites Ashland by IHG

11.6 km from Windsor Ski Lift

Lorenzo

RM392

RM437 total

includes taxes & fees

19 Nov - 20 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 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.

4. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Nicholas

RM398

RM485 total

includes taxes & fees

8 Nov - 9 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 hotel room with a large bed, a separate sitting area, a large bathtub, and a flat-screen TV.

5. Best Western Windsor Inn

11.9 km from Windsor Ski Lift

Deborah

RM434

RM483 total

includes taxes & fees

31 Oct - 1 Nov

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

A covered outdoor seating area with benches and potted plants.

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

Sarah

RM279

RM311 total

includes taxes & fees

25 Oct - 26 Oct

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.

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

7. Callahan's Mountain Lodge

8.8 km from Windsor Ski Lift

Meena

RM397

RM464 total

includes taxes & fees

30 Oct - 31 Oct

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

A well-maintained garden with a paved walkway, surrounded by lush greenery and trees.

8. Lithia Springs Resort

15.4 km from Windsor Ski Lift

RM382

RM469 total

includes taxes & fees

8 Nov - 9 Nov

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 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.

9. Plaza Inn & Suites at Ashland Creek

12.9 km from Windsor Ski Lift

Bill

RM474

RM528 total

includes taxes & fees

1 Nov - 2 Nov

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

A breakfast bar with a toaster, fruit bowl, bread baskets, and a display case with pastries.

10. Prospero's Flagship Inn

11.4 km from Windsor Ski Lift

Mary

RM301

RM336 total

includes taxes & fees

1 Nov - 2 Nov

A two-story building with a wooden facade, large windows, and a front porch with chairs.

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, a wooden dresser, a chair, and a bed.

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

11. The Peerless Hotel by WanderLodges

Historic Railroad District, 12.6 km from Windsor Ski Lift

Jaye

RM380

RM646 total

includes taxes & fees

26 Oct - 27 Oct

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 high ceiling, ornate chandelier, and multiple seating areas.

12. Ashland Springs Hotel

Historic Downtown District, 12.4 km from Windsor Ski Lift

Duff

RM347

RM450 total

includes taxes & fees

19 Nov - 20 Nov

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

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

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

13. Winchester Inn

Historic Downtown District, 12.3 km from Windsor Ski Lift

Ellen

RM545

RM673 total

includes taxes & fees

9 Nov - 10 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

RM290

RM324 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

15. Barclay Klum House by WanderLodges

12.2 km from Windsor Ski Lift

Melissa

RM481

RM1,060 total

includes taxes & fees

25 Oct - 26 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.

16. Country Willows Inn and Estate

10 km from Windsor Ski Lift

Diane

RM791

RM803 total

includes taxes & fees

1 Nov - 2 Nov

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

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 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.

17. Hanna's House by WanderLodges

Historic Railroad District, 12.3 km from Windsor Ski Lift

Robert

RM503

RM875 total

includes taxes & fees

2 Nov - 3 Nov

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

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.

A rustic building with a porch, surrounded by lush greenery and a sign indicating it is a forest.

18. Arden Forest Inn

13.3 km from Windsor Ski Lift

Jean

RM558

RM622 total

includes taxes & fees

2 Nov - 3 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 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.

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

Historic Downtown District, 12.8 km from Windsor Ski Lift

Thomas

RM469

RM523 total

includes taxes & fees

7 Nov - 8 Nov

A Victorian-style building with ornate architectural details, large windows, and a red door.

A room with a glass display case containing wine bottles and glasses, a white chair, and a large window with curtains.

A patio area with string lights, potted plants, and a stone pathway.

A room with a bay window, two upholstered chairs, a round ottoman, and a small wooden table.

20. McCall House Boutique Inn

Historic Downtown District, 12.6 km from Windsor Ski Lift

Elizabeth

RM639

RM713 total

includes taxes & fees

1 Nov - 2 Nov

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Compare top hotels near Windsor Ski Lift

Stratford Inn Siskiyou-Hargadine Historic District, 12.1 km from Windsor Ski Lift View	Comfort Inn & Suites Ashland 15.9 km from Windsor Ski Lift View	Holiday Inn Express & Suites Ashland by IHG 11.6 km from Windsor Ski Lift View	Ashland Hills Hotel & Suites 11.8 km from Windsor Ski Lift View	Best Western Windsor Inn 11.9 km from Windsor Ski Lift View
9.4 Exceptional 1,798 reviews	9.0 Wonderful 1,057 reviews	9.2 Wonderful 1,004 reviews	8.8 Excellent 1,563 reviews	9.0 Wonderful 1,000 reviews
RM381 RM425 total includes taxes & fees 26 Oct - 27 Oct	RM458 RM465 total includes taxes & fees 22 Nov - 23 Nov	RM392 RM437 total includes taxes & fees 19 Nov - 20 Nov	RM398 RM485 total includes taxes & fees 8 Nov - 9 Nov	RM434 RM483 total includes taxes & fees 31 Oct - 1 Nov

Top Windsor Ski Lift Hotel Reviews

Comfort Inn & Suites Ashland

10/10 Excellent

"very good hotel 🏨 and clean"

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."

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

8/10 Good

"No other comments."

Ashland Springs Hotel

10/10 Excellent

"Location is so nice. Love Ashland. Been staying here for years. Watched this hotel go from wore out to closed to refurbished to new owners over the last 50 years. Love these 1920’s hotels so happy they are keeping it going."

Relax Inn At Ashland

8/10 Good

"nice cozy and charming motel, close to shops and affordable"

Plaza Inn & Suites at Ashland Creek

8/10 Good

"There was not enough easily accessible parking and a lot of it was for compact cars. As senior citizens, we found the lower level to be a challenge."

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."

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."

Winchester Inn

10/10 Excellent

"Amazing breakfasts, friendly staff, best location"

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

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for Windsor Ski Lift hotels

1. Stratford Inn

2. Comfort Inn & Suites Ashland

3. Holiday Inn Express & Suites Ashland by IHG

4. Ashland Hills Hotel & Suites

5. Best Western Windsor Inn

6. Timbers INN and Suites

7. Callahan's Mountain Lodge

8. Lithia Springs Resort

9. Plaza Inn & Suites at Ashland Creek

10. Prospero's Flagship Inn

11. The Peerless Hotel by WanderLodges

12. Ashland Springs Hotel

13. Winchester Inn

14. Ashland Commons Hostel

15. Barclay Klum House by WanderLodges

16. Country Willows Inn and Estate

17. Hanna's House by WanderLodges

18. Arden Forest Inn

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

20. McCall House Boutique Inn

Compare top hotels near Windsor Ski Lift

Stratford Inn

Comfort Inn & Suites Ashland

Holiday Inn Express & Suites Ashland by IHG

Ashland Hills Hotel & Suites

Best Western Windsor Inn

Top Windsor Ski Lift Hotel Reviews

Comfort Inn & Suites Ashland

Cedarwood Inn of Ashland

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

Ashland Springs Hotel

Relax Inn At Ashland

Plaza Inn & Suites at Ashland Creek

Ashland Motel - Oregon

Country Willows Inn and Estate

Winchester Inn

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