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.

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

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

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

1. Stratford Inn

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

David

AED 343

AED 383 total

includes taxes & fees

1 Nov - 2 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 hotel room with a large bed, a desk, and a window with curtains.

2. Timbers INN and Suites

11.3 km from Windsor Ski Lift

Sarah

AED 236

AED 263 total

includes taxes & fees

26 Oct - 27 Oct

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.

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

3. Best Western Windsor Inn

11.9 km from Windsor Ski Lift

Ross

AED 413

AED 461 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.

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

An outdoor patio with lounge chairs and a table, surrounded by autumn foliage and a view of mountains.

A spacious living room with a high ceiling, large windows, and a mix of seating arrangements including a sofa and chairs.

4. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Nicholas

AED 393

AED 475 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 bathroom with a wooden door, a sink with a mirror, a towel rack, a coffee maker, and a black refrigerator.

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.

5. Holiday Inn Express & Suites Ashland by IHG

11.6 km from Windsor Ski Lift

Lorenzo

AED 375

AED 418 total

includes taxes & fees

16 Nov - 17 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 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

Bill

AED 362

AED 368 total

includes taxes & fees

22 Nov - 23 Nov

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 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.

7. Prospero's Flagship Inn

11.4 km from Windsor Ski Lift

Mary

AED 245

AED 274 total

includes taxes & fees

31 Oct - 1 Nov

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.

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

8. Callahan's Mountain Lodge

8.8 km from Windsor Ski Lift

Meena

AED 357

AED 417 total

includes taxes & fees

30 Oct - 31 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 traditional living room with a fireplace, patterned furniture, and large windows with curtains.

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

9. Plaza Inn & Suites at Ashland Creek

12.9 km from Windsor Ski Lift

Bill

AED 426

AED 475 total

includes taxes & fees

1 Nov - 2 Nov

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

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

10. Lithia Springs Resort

15.4 km from Windsor Ski Lift

Steven

AED 344

AED 422 total

includes taxes & fees

16 Nov - 17 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, wooden floor, green-framed windows, and two upholstered chairs.

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

Lindsay

AED 342

AED 582 total

includes taxes & fees

27 Oct - 28 Oct

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 kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with stools.

12. Ashland Commons Hostel

12.9 km from Windsor Ski Lift

Sam

AED 243

AED 271 total

includes taxes & fees

24 Nov - 25 Nov

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

13. Country Willows Inn and Estate

10 km from Windsor Ski Lift

Diane

AED 712

AED 722 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

14. Winchester Inn

Historic Downtown District, 12.3 km from Windsor Ski Lift

Ellen

AED 439

AED 546 total

includes taxes & fees

26 Oct - 27 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 spacious living room with large windows, dark wooden flooring, and a cozy seating area with multiple chairs and a bench.

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

Historic Downtown District, 12.8 km from Windsor Ski Lift

Thomas

AED 422

AED 471 total

includes taxes & fees

7 Nov - 8 Nov

A wreath decorated with red and gold ornaments, pine cones, and greenery, hanging on a post in front of a house with a snow-covered roof.

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

16. Arden Forest Inn

13.3 km from Windsor Ski Lift

Jean

AED 502

AED 560 total

includes taxes & fees

3 Nov - 4 Nov

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

A spacious lobby with a grand chandelier, a fireplace, and a large window offering a view of the outdoors.

A spacious lobby with a high ceiling, ornate chandelier, and multiple seating areas.

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

17. Ashland Springs Hotel

Historic Downtown District, 12.4 km from Windsor Ski Lift

Duff

AED 344

AED 440 total

includes taxes & fees

15 Nov - 16 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 dining table with chairs, a refrigerator, and a built-in oven.

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

A spacious living room with a wooden floor, a sofa, a dining table, and a kitchen area visible through an open doorway.

18. Hanna's House by WanderLodges

Historic Railroad District, 12.3 km from Windsor Ski Lift

Robert

AED 398

AED 726 total

includes taxes & fees

3 Nov - 4 Nov

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

A modern living room with a brown leather sofa, a black coffee table, and a kitchen area with wooden cabinets and a marble backsplash.

19. Baymont by Wyndham

11.7 km from Windsor Ski Lift

Virginia

AED 294

AED 328 total

includes taxes & fees

24 Nov - 25 Nov

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 hotel reception area with a Dell computer, a calendar, and a window with a view of the outside.

A coffee machine with a digital display, a coffee pot, a cup, and a coffee pod.

20. Ashland Motel - Oregon

11.5 km from Windsor Ski Lift

Madrik A.

AED 245

AED 273 total

includes taxes & fees

15 Nov - 16 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
Timbers INN and Suites	8.8 Excellent 1,006 reviews	View
Best Western Windsor Inn	9.0 Wonderful 1,003 reviews	View
Ashland Hills Hotel & Suites	8.8 Excellent 1,567 reviews	View
Holiday Inn Express & Suites Ashland by IHG	9.2 Wonderful 1,005 reviews	View

Top Windsor Ski Lift Hotel Reviews

Ashland Hills Hotel & Suites

10/10 Excellent

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

Plaza Inn & Suites at Ashland Creek

10/10 Excellent

"Not only loved the hotel and all the amenities, but the location as well! A perfect place to stay to be near the Theater and the town. It was quiet and I felt it to be a safe neighborhood as well!"

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."

Timbers INN and Suites

8/10 Good

"The facility fit the needs that we required on this trip. One small challenge, one of the electrical outlets that had a lamp plugged into it was not working. But that’s OK. Everything was clean and satisfactory for our needs like I said I will definitely use them again on my next trip."

Callahan's Mountain Lodge

10/10 Excellent

"Our stay at Callan's was an abloute success. I needed to unwind and relax this tire body of mine. The hot tub in our room was the perfect medicine, The food was to die for. I was not expecting that at all. I usually do not like mac and cheese and now I have to take a special trip down there with my daughter-in-law for her have some. My only complaint is that they don't serve beef stroganoff on the weekends. Prime rib is on the weekend menu and I have never liked prime rib,"

Stratford Inn

10/10 Excellent

"Staff was friendly and helpful."

Country Willows Inn and Estate

10/10 Excellent

"Breakfast was amazing. Clean room. Great staff."

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."

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 AED 263

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Treat yourself

Be picky

Check prices for these dates

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Star rating

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Our top choices for Windsor Ski Lift hotels

1. Stratford Inn

2. Timbers INN and Suites

3. Best Western Windsor Inn

4. Ashland Hills Hotel & Suites

5. Holiday Inn Express & Suites Ashland by IHG

6. Comfort Inn & Suites Ashland

7. Prospero's Flagship Inn

8. Callahan's Mountain Lodge

9. Plaza Inn & Suites at Ashland Creek

10. Lithia Springs Resort

11. The Peerless Hotel by WanderLodges

12. Ashland Commons Hostel

13. Country Willows Inn and Estate

14. Winchester Inn

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

16. Arden Forest Inn

17. Ashland Springs Hotel

18. Hanna's House by WanderLodges

19. Baymont by Wyndham

20. Ashland Motel - Oregon

Compare popular hotels close to Windsor Ski Lift

Top Windsor Ski Lift Hotel Reviews

Ashland Hills Hotel & Suites

Plaza Inn & Suites at Ashland Creek

Ashland Springs Hotel

Timbers INN and Suites

Callahan's Mountain Lodge

Stratford Inn

Country Willows Inn and Estate

Comfort Inn & Suites Ashland

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