The Best Hotels Closest to Windsor Ski Lift in Ashland - 2026 Updated Prices

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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.

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.

1. Stratford Inn

Siskiyou-Hargadine Historic District, 7.5 mi from Windsor Ski Lift

David

£73

includes taxes & fees

13 Oct - 14 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.

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

2. Callahan's Mountain Lodge

5.5 mi from Windsor Ski Lift

Karen

£108

includes taxes & fees

26 Oct - 27 Oct

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.

3. Holiday Inn Express & Suites Ashland by IHG

7.2 mi from Windsor Ski Lift

Adam

£80

includes taxes & fees

26 Oct - 27 Oct

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

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

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.

4. Prospero's Flagship Inn

7.1 mi from Windsor Ski Lift

Jenny

£62

includes taxes & fees

25 Oct - 26 Oct

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

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.

5. Best Western Windsor Inn

7.4 mi from Windsor Ski Lift

Dennis

£95

includes taxes & fees

4 Oct - 5 Oct

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 hotel with a swimming pool, multiple balconies, and a view of the surrounding landscape.

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

6. Ashland Hills Hotel & Suites

7.3 mi from Windsor Ski Lift

Krishnaharsha

£105

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.

7. Country Willows Inn and Estate

6.2 mi from Windsor Ski Lift

raymon

£194

includes taxes & fees

29 Sept - 30 Sept

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 two-story house with a porch, a staircase, and a garden.

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

8. Lithia Springs Resort

9.6 mi from Windsor Ski Lift

Steven

£120

includes taxes & fees

27 Oct - 28 Oct

A hotel entrance with outdoor seating, potted plants, and a well-lit facade.

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.

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

9. Comfort Inn & Suites Ashland

9.9 mi from Windsor Ski Lift

Christina

£86

includes taxes & fees

5 Oct - 6 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 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.

10. Plaza Inn & Suites at Ashland Creek

8 mi from Windsor Ski Lift

Alan

£136

includes taxes & fees

5 Oct - 6 Oct

A balcony with a view of a residential area, a black pickup truck, and a white RV parked in the foreground.

A man sitting at a table with a notebook, writing. The table has a cup, a small plant, and some pumpkins on it.

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

11. Ashland Commons Hostel

8 mi from Windsor Ski Lift

Brenda

£50

includes taxes & fees

6 Oct - 7 Oct

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

A building with a snow-covered entrance and a tree in the foreground.

12. Ashland Springs Hotel

Historic Downtown District, 7.7 mi from Windsor Ski Lift

Susan

£127

includes taxes & fees

28 Oct - 29 Oct

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.

13. The Peerless Hotel by WanderLodges

Historic Railroad District, 7.8 mi from Windsor Ski Lift

Jaye

£170

includes taxes & fees

29 Sept - 30 Sept

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

A spacious living room with a large TV, comfortable seating, and a chandelier.

14. Barclay Klum House by WanderLodges

7.6 mi from Windsor Ski Lift

Melissa

£207

includes taxes & fees

4 Oct - 5 Oct

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 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.

15. Winchester Inn

Historic Downtown District, 7.6 mi from Windsor Ski Lift

Deirdre

£135

includes taxes & fees

26 Oct - 27 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.

16. Palm Cottages

7.2 mi from Windsor Ski Lift

Eric

£169

includes taxes & fees

29 Sept - 30 Sept

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

A restaurant with multiple tables and booths, large windows with a view of trees, and hanging decorative light fixtures.

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

Historic Downtown District, 7.9 mi from Windsor Ski Lift

Dawn

£142

includes taxes & fees

4 Oct - 5 Oct

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

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

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

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

18. McCall House Boutique Inn

Historic Downtown District, 7.8 mi from Windsor Ski Lift

Elizabeth

£232

includes taxes & fees

5 Oct - 6 Oct

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

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

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

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

19. Abigail’s Bed & Breakfast Inn

Skidmore Academy Historic District, 8.3 mi from Windsor Ski Lift

Kim

£219

includes taxes & fees

27 Oct - 28 Oct

A hotel room with two beds, a large framed picture of a mountain, a lamp, and a window with curtains.

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

A hotel kitchen with marble tiles, a coffee machine, a refrigerator, and a counter with various items.

A building with a stone facade, a glass door entrance, and a visible interior with a counter and signage.

20. Baymont by Wyndham

7.3 mi from Windsor Ski Lift

Brian

£73

includes taxes & fees

6 Oct - 7 Oct

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Compare popular hotels close to Windsor Ski Lift

Property	Property class	Guest rating
Stratford Inn	9.4 Exceptional 1,794 reviews	View
Callahan's Mountain Lodge	8.8 Excellent 1,144 reviews	View
Holiday Inn Express & Suites Ashland by IHG	9.2 Wonderful 1,006 reviews	View
Prospero's Flagship Inn	8.4 Very good 1,475 reviews	View
Best Western Windsor Inn	9.0 Wonderful 1,004 reviews	View

Top Windsor Ski Lift Hotel Reviews

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."

Stratford Inn

8/10 Good

"Clean and plain but very nice, convient and a real Shakespeare vibe."

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.

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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 311 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.

Search Hotels Near Windsor Ski Lift, Ashland

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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. Callahan's Mountain Lodge

3. Holiday Inn Express & Suites Ashland by IHG

4. Prospero's Flagship Inn

5. Best Western Windsor Inn

6. Ashland Hills Hotel & Suites

7. Country Willows Inn and Estate

8. Lithia Springs Resort

9. Comfort Inn & Suites Ashland

10. Plaza Inn & Suites at Ashland Creek

11. Ashland Commons Hostel

12. Ashland Springs Hotel

13. The Peerless Hotel by WanderLodges

14. Barclay Klum House by WanderLodges

15. Winchester Inn

16. Palm Cottages

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

18. McCall House Boutique Inn

19. Abigail’s Bed & Breakfast Inn

20. Baymont by Wyndham

Compare popular hotels close to Windsor Ski Lift

Top Windsor Ski Lift Hotel Reviews

Prospero's Flagship Inn

Cedarwood Inn of Ashland

Stratford Inn

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