The Best Hotels Closest to Windsor Ski Lift in Ashland for 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

NT$2,977

NT$3,319 total

includes taxes & fees

Oct 12 - Oct 13

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

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

2. Holiday Inn Express & Suites Ashland by IHG

11.6 km from Windsor Ski Lift

Adam

NT$3,048

NT$3,399 total

includes taxes & fees

Oct 26 - Oct 27

A wooden balcony with a view of a forested area.

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

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

3. Callahan's Mountain Lodge

8.8 km from Windsor Ski Lift

Karen

NT$4,258

NT$4,799 total

includes taxes & fees

Oct 1 - Oct 2

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.

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

NT$3,573

NT$3,984 total

includes taxes & fees

Oct 4 - Oct 5

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 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.

5. Ashland Hills Hotel & Suites

11.8 km from Windsor Ski Lift

Krishnaharsha

NT$3,301

NT$3,998 total

includes taxes & fees

Oct 26 - Oct 27

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 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.

6. Prospero's Flagship Inn

11.4 km from Windsor Ski Lift

Jenny

NT$2,544

NT$2,836 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

7. Comfort Inn & Suites Ashland

15.9 km from Windsor Ski Lift

Christina

NT$3,572

NT$3,626 total

includes taxes & fees

Oct 5 - Oct 6

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 traditional living room with a fireplace, patterned furniture, and large windows with curtains.

8. Plaza Inn & Suites at Ashland Creek

12.9 km from Windsor Ski Lift

Alan

NT$5,116

NT$5,704 total

includes taxes & fees

Oct 5 - Oct 6

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

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

9. Barclay Klum House by WanderLodges

12.2 km from Windsor Ski Lift

Melissa

NT$4,430

NT$9,011 total

includes taxes & fees

Sep 29 - Sep 30

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

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.

A spacious room with a large dining table, chairs, a sofa, and a coffee table. There are ceiling fans, large windows, and potted plants.

10. The Peerless Hotel by WanderLodges

Historic Railroad District, 12.6 km from Windsor Ski Lift

Jaye

NT$4,315

NT$6,546 total

includes taxes & fees

Oct 6 - Oct 7

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

A bar area with a marble countertop, wine bottles, and glasses. There are hanging pendant lights and a 'No Minors' sign.

11. Lithia Springs Resort

15.4 km from Windsor Ski Lift

Steven

NT$4,335

NT$5,035 total

includes taxes & fees

Oct 27 - Oct 28

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.

12. Country Willows Inn and Estate

10 km from Windsor Ski Lift

raymon

NT$8,046

NT$8,166 total

includes taxes & fees

Sep 29 - Sep 30

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.

13. Ashland Commons Hostel

12.9 km from Windsor Ski Lift

Brenda

NT$2,258

NT$2,518 total

includes taxes & fees

Sep 29 - Sep 30

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 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.

14. Ashland Springs Hotel

Historic Downtown District, 12.4 km from Windsor Ski Lift

Susan

NT$4,335

NT$5,334 total

includes taxes & fees

Oct 28 - Oct 29

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

15. Winchester Inn

Historic Downtown District, 12.3 km from Windsor Ski Lift

Deirdre

NT$4,622

NT$5,677 total

includes taxes & fees

Oct 26 - Oct 27

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 dining table set with plates, cutlery, and glasses, with two leather stools and a window with blinds in the background.

16. Palm Cottages

11.6 km from Windsor Ski Lift

Eric

NT$6,381

NT$7,114 total

includes taxes & fees

Sep 29 - Sep 30

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.

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

Historic Downtown District, 12.8 km from Windsor Ski Lift

Dawn

NT$5,367

NT$5,984 total

includes taxes & fees

Oct 4 - Oct 5

A spacious kitchen with a central island, bar stools, and a fireplace.

A modern bathroom with a sink, mirror, and toiletries.

A cozy living room with a sofa, a woven hanging chair, a round pouf, and a large abstract painting.

A spacious dining area with a long wooden table and cushioned chairs, a bookshelf, and a fireplace.

18. Paschal Winery

19.6 km from Windsor Ski Lift

Christine

NT$4,430

NT$13,450 total

includes taxes & fees

Sep 29 - Sep 30

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

A spacious living room with a large sofa, a dining area with a table and chairs, and a chandelier.

19. McCall House Boutique Inn

Historic Downtown District, 12.6 km from Windsor Ski Lift

Elizabeth

NT$8,745

NT$9,751 total

includes taxes & fees

Oct 5 - Oct 6

A two-story house with a porch, surrounded by a well-maintained garden with various flowers and shrubs.

A garden pathway leading to a building with a pergola and hanging flower baskets.

A porch with three wooden chairs with floral upholstery, a wooden bench, and a view of a house in the background.

A spacious dining area with a wooden table and chairs, large windows with a view of the outdoors, and a chandelier.

20. Abigail’s Bed & Breakfast Inn

Skidmore Academy Historic District, 13.4 km from Windsor Ski Lift

Kim

NT$8,256

NT$9,206 total

includes taxes & fees

Oct 27 - Oct 28

View all properties

Compare popular hotels close to Windsor Ski Lift

Property	Property class	Guest rating
Stratford Inn	9.4 Exceptional 1,795 reviews	View
Holiday Inn Express & Suites Ashland by IHG	9.2 Wonderful 1,006 reviews	View
Callahan's Mountain Lodge	8.8 Excellent 1,144 reviews	View
Best Western Windsor Inn	9.0 Wonderful 1,004 reviews	View
Ashland Hills Hotel & Suites	8.8 Excellent 1,540 reviews	View

Top Windsor Ski Lift Hotel Reviews

Stratford Inn

10/10 Excellent

"Our room was great, a one bedroom with a king sized bed and a separate kitchen and living area, clean and newly renovated. Plenty of room to host a pre-dinner happy hour with friends. It is within walking distance of the Oregon Shakespeare theaters and downtown. The continental breakfast was fine with gluten free options."

Prospero's Flagship Inn

8/10 Good

"My room was spacious and everything worked. The linens were above average for a hotel of this type.My only comment is that the carpet very much needs cleaning."

Cedarwood Inn of Ashland

10/10 Excellent

"We had a nice stay here. Room was large and clean. Staff were very nice and made sure that we were happy with everything. Will definitely stay here the next time I'm in the area."

Timbers INN and Suites

8/10 Good

"If you just need some place to sleep, and something affordable, this is perfect. The furnishings weren't fabulous, but the beds and pillows were comfortable and the room was clean."

Best Western Windsor Inn

8/10 Good

"Staff were helpful and pleasant. Breakfast was generous. Bed was comfy."

Comfort Inn & Suites Ashland

8/10 Good

"Great location , staff super friendly . Coukd use a larger lounge area"

Baymont by Wyndham

8/10 Good

"Hotel was clean , and had a great view. Loved having a soap dispenser in the room for hand washing. We will stay here again."

Palm Cottages

10/10 Excellent

"Cute motel style place. Room was cute and clean. Walking distance (about 1 mile) to downtown Ashland restaurants and shows."

Relax Inn At Ashland

10/10 Excellent

"Clean, quiet, bright room, easy access, walk to restaurants/pub, Mexican restaurant next door with dog friendly patio, vacant lot on other side to walk dogs, inexpensive but a $20 fee for dog."

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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 311 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 NT$2,518

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Windsor Ski Lift hotels

1. Stratford Inn

2. Holiday Inn Express & Suites Ashland by IHG

3. Callahan's Mountain Lodge

4. Best Western Windsor Inn

5. Ashland Hills Hotel & Suites

6. Prospero's Flagship Inn

7. Comfort Inn & Suites Ashland

8. Plaza Inn & Suites at Ashland Creek

9. Barclay Klum House by WanderLodges

10. The Peerless Hotel by WanderLodges

11. Lithia Springs Resort

12. Country Willows Inn and Estate

13. Ashland Commons Hostel

14. Ashland Springs Hotel

15. Winchester Inn

16. Palm Cottages

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

18. Paschal Winery

19. McCall House Boutique Inn

20. Abigail’s Bed & Breakfast Inn

Compare popular hotels close to Windsor Ski Lift

Top Windsor Ski Lift Hotel Reviews

Stratford Inn

Prospero's Flagship Inn

Cedarwood Inn of Ashland

Timbers INN and Suites

Best Western Windsor Inn

Comfort Inn & Suites Ashland

Baymont by Wyndham

Palm Cottages

Relax Inn At 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

Explore a world of travel with Expedia