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

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Compare popular hotels close to Windsor Ski Lift

Property	Property class	Guest rating	Breakfast included	Pool	Spa	Pet friendly	WiFi included
Callahan's Mountain Lodge	3.0 star property	8.8 Excellent 1,145 reviews						View
Country Willows Inn and Estate	4.0 star property	9.8 Exceptional 37 reviews						View
Prospero's Flagship Inn	2.5 star property	8.6 Excellent 1,374 reviews						View
Ashland Commons Hostel	2.0 star property	9.4 Exceptional 56 reviews						View
Ashland Hills Hotel & Suites	3.0 star property	8.8 Excellent 1,490 reviews						View

Top Windsor Ski Lift Hotel Reviews

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

10/10 Excellent

"The property is spacious and close to SOU campus and the theaters."

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

10/10 Excellent

"This is a great visit and a great vacation spot to stay, including if you want to swim unfortunately they do not have an exercise room so you’re only amounts of exercise would be swimming. But that was not aThis is a great visit and a great vacation spot to stay, including if you want to swim unfortunately they do not have a exercise room so you’re only amounts of exercise would be swimming. But that was not a downfall for me."

Best Western Windsor Inn

Best Western Windsor Inn

8/10 Good

"The individual at the front desk was unpleasant and unhelpful to my wife on the morning of check out, and when I went down to fetch the items, she was in the same mood. Later in the morning at check out, her day had apparently not gotten any better with the progression of guests. On the high side, I enjoyed the use of the pool/hot tub area, but it did not appear to be cleaned overnight. I used the gym/work out space (they were quite strict about the time to go in), but again the place was not particularly clean, with cups and towels around, when I was the very first individual present in the morning. The breakfast helper was pleasant, and the food reasonably palatable. For novelty sake I tried the pancake making machine, perhaps version 2.0 will be more effective at actually completely cooking the pancakes. The vista was beautiful, and the setting sun against the mountains and trees while relaxing in the hot tub was almost Elizabethan magic (especially after A Midsummer's Night Dream)."

Stratford Inn

Stratford Inn

10/10 Excellent

"The well-designed Stratford Inn provided an excellent hotel stay. The rooms were clean and comfortable with excellent HVAC and Internet services. The heart-healthy breakfast contained a large variety of delicious choices and the location in the heart of Ashland allowed walking access to restaurants and theaters."

Hotels near other Windsor Ski Lift attractions

Mount Ashland Ski Area

8.6/5 (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.

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 325 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?

Prospero's Flagship Inn is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and a restaurant. You'll find it 7.1 mi (11.4 km) from Windsor Ski Lift. Other good choices in the area include Ashland Hills Hotel & Suites and Stratford Inn.

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.

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