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Check prices for these dates

This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

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Our top choices for Windsor Ski Lift hotels

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

1. Prospero's Flagship Inn

Prospero's Flagship Inn
2.5 star property
11.4 km from Windsor Ski Lift
8.4 out of 10, Very good, (1,496 reviews)
"We enjoyed our stay very much. The location was good; the staff great and our room was very nice"
United States
Mary
The price is SAR 207
SAR 231 total
includes taxes & fees
22 Nov - 23 Nov
Prospero's Flagship Inn
A hotel entrance with outdoor seating, potted plants, and a well-lit facade.

2. Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
2.5 star property
15.9 km from Windsor Ski Lift
9.0 out of 10, Wonderful, (1,069 reviews)
"Clean rooms, good breakfast, conveniently located."
United States
Bill
The price is SAR 354
SAR 359 total
includes taxes & fees
13 Dec - 14 Dec
Comfort Inn & Suites Ashland
Exterior

3. Best Western Windsor Inn

Best Western Windsor Inn
2.5 star property
11.9 km from Windsor Ski Lift
9.0 out of 10, Wonderful, (1,000 reviews)
"Great location, clean room, friendly staff"
United States
Ross
The price is SAR 426
SAR 474 total
includes taxes & fees
14 Dec - 15 Dec
Best Western Windsor Inn
Exterior

4. Callahan's Mountain Lodge

Callahan's Mountain Lodge
3.0 star property
8.8 km from Windsor Ski Lift
8.8 out of 10, Excellent, (1,124 reviews)
"Cozy getaway. Loved our stay here."
United States
Cameron
The price is SAR 331
SAR 392 total
includes taxes & fees
11 Dec - 12 Dec
Callahan's Mountain Lodge
A Holiday Inn Express hotel with a two-story structure, a parking lot, and a landscaped area with shrubs and a tall tree.

5. Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG
2.5 star property
11.6 km from Windsor Ski Lift
9.2 out of 10, Wonderful, (1,001 reviews)
"Very friendly staff."
Canada
Tanis
The price is SAR 360
SAR 402 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Ashland by IHG
A spacious lobby with a large wooden floor, a green peace sign decoration, and a large window offering a view of the outdoors.

6. Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
3.0 star property
11.8 km from Windsor Ski Lift
8.8 out of 10, Excellent, (1,576 reviews)
"Great hotel!"
United States
Nicholas
The price is SAR 324
SAR 399 total
includes taxes & fees
14 Dec - 15 Dec
Ashland Hills Hotel & Suites
A swimming pool with a clear view of the poolside area, including lounge chairs and a covered seating area.

7. Timbers INN and Suites

Timbers INN and Suites
2.0 star property
11.3 km from Windsor Ski Lift
8.8 out of 10, Excellent, (1,006 reviews)
"Our room was very clean and comfortable and our staff interaction was great. We’ll definitely stay here again when we come to Ashland."
United States
Sarah
The price is SAR 270
SAR 301 total
includes taxes & fees
22 Nov - 23 Nov
Timbers INN and Suites
A two-story building with a wooden facade, large windows, and a front porch with chairs.

8. The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges
2.0 star property
Historic Railroad District, 12.6 km from Windsor Ski Lift
9.6 out of 10, Exceptional, (119 reviews)
"My room was clean, bed was comfortable. It was really nice and central to restaurants, coffee shops and downtown. It was nice having a door code instead of keys etc. would stay here again"
Canada
Lindsay
The price is SAR 309
SAR 550 total
includes taxes & fees
23 Nov - 24 Nov
The Peerless Hotel by WanderLodges
An outdoor dining area with a table set for two, surrounded by chairs, a red umbrella, and a stone water feature.

9. Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek
3.0 star property
12.9 km from Windsor Ski Lift
9.0 out of 10, Wonderful, (1,000 reviews)
"Very nicece hotel and perfect location for walking and exploring Ashland."
United States
Heather
The price is SAR 436
SAR 486 total
includes taxes & fees
16 Nov - 17 Nov
Plaza Inn & Suites at Ashland Creek
A backyard with a swimming pool, patio furniture, a small pond, and a wooden cabin.

10. Country Willows Inn and Estate

Country Willows Inn and Estate
4.0 star property
10 km from Windsor Ski Lift
9.8 out of 10, Exceptional, (46 reviews)
"A beautiful serene landscape compliments the beautifully decorated and very comfy rooms. Beds and pillows were divine. Breakfast was epicurean."
United States
Diane
The price is SAR 713
SAR 724 total
includes taxes & fees
14 Nov - 15 Nov
Country Willows Inn and Estate
A balcony with a view of a residential area, a black pickup truck, and a white RV parked in the foreground.

11. Ashland Commons Hostel

Ashland Commons Hostel
2.0 star property
12.9 km from Windsor Ski Lift
9.4 out of 10, Exceptional, (76 reviews)
"Great place to stay. Excellent location."
United States
Sam
The price is SAR 269
SAR 300 total
includes taxes & fees
16 Nov - 17 Nov
Ashland Commons Hostel
A spacious lobby with a reception desk, seating area, and large windows.

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

The Bard's Inn, BW Signature Collection by Best Western
2.5 star property
Historic Downtown District, 12.8 km from Windsor Ski Lift
8.4 out of 10, Very good, (1,004 reviews)
"Love this place"
United States
Jess
The price is SAR 303
SAR 338 total
includes taxes & fees
24 Nov - 25 Nov
The Bard's Inn, BW Signature Collection by Best Western
A grand lobby with a high ceiling, large windows, and a central staircase.

13. Ashland Springs Hotel

Ashland Springs Hotel
3.0 star property
Historic Downtown District, 12.4 km from Windsor Ski Lift
9.2 out of 10, Wonderful, (1,001 reviews)
"Cutest hotel ever! Will stay again."
Canada
Tamara
The price is SAR 319
SAR 414 total
includes taxes & fees
14 Dec - 15 Dec
Ashland Springs Hotel
A hotel room with a desk, laptop, two beds, and a round mirror.

14. Ashland Motel - Oregon

Ashland Motel - Oregon
2.0 star property
11.5 km from Windsor Ski Lift
8.0 out of 10, Very good, (251 reviews)
"Clean, basic room that is walking distance to downtown Ashland."
United States
Madrik A.
The price is SAR 272
SAR 303 total
includes taxes & fees
15 Nov - 16 Nov
Ashland Motel - Oregon
A Victorian-style building with ornate architectural details, large windows, and a red door.

15. McCall House Boutique Inn

McCall House Boutique Inn
4.0 star property
Historic Downtown District, 12.6 km from Windsor Ski Lift
9.6 out of 10, Exceptional, (620 reviews)
"All good; would stay again. Great breakfast too"
United States
Elizabeth
The price is SAR 591
SAR 659 total
includes taxes & fees
14 Nov - 15 Nov
McCall House Boutique Inn
A hotel room with a bed, bedside tables, a desk, a chair, a dresser, and a painting on the wall.

16. Baymont by Wyndham Ashland OR

Baymont by Wyndham Ashland OR
2.5 star property
11.7 km from Windsor Ski Lift
7.8 out of 10, Good, (709 reviews)
"Location is great."
United States
Brian
The price is SAR 304
SAR 339 total
includes taxes & fees
27 Nov - 28 Nov
Baymont by Wyndham Ashland OR
A two-story house with a porch, surrounded by a well-maintained garden with various flowers and shrubs.

17. Abigail’s Bed & Breakfast Inn

Abigail’s Bed & Breakfast Inn
3.5 star property
Skidmore Academy Historic District, 13.4 km from Windsor Ski Lift
9.4 out of 10, Exceptional, (66 reviews)
"I have stayed in many bed and breakfasts over the years and this one ranks a perfect 10! Very clean,very friendly hosts, the absolute best breakfast of any B & B I've been to. If I'm going through Ashland in the future, this is my go to lodging. This felt like home! Hosts also were extremely helpful and knowledgeable about local dining. "
United States
Kim
The price is SAR 713
SAR 795 total
includes taxes & fees
14 Nov - 15 Nov
Abigail’s Bed & Breakfast Inn
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a covered seating area.

18. Palm Cottages

Palm Cottages
2.5 star property
11.6 km from Windsor Ski Lift
9.2 out of 10, Wonderful, (233 reviews)
"Palm Cottages is a clean and wonderful boutique hotel on the outskirts of downtown Ashland. We only stayed one night but we will definitely be back again some day. Thank you 🙏"
United States
Eric
The price is SAR 762
SAR 849 total
includes taxes & fees
14 Nov - 15 Nov
Palm Cottages
A dining area with a wooden table and chairs, a potted plant, and a window with blinds.

19. Cedarwood Inn of Ashland

Cedarwood Inn of Ashland
2.0 star property
10.9 km from Windsor Ski Lift
7.4 out of 10, Good, (1,000 reviews)
"Good location, good value."
United States
Toby
The price is SAR 267
SAR 298 total
includes taxes & fees
25 Nov - 26 Nov
Cedarwood Inn of Ashland
A spacious kitchen with a central island, bar stools, and a fireplace.

20. Paschal Winery

Paschal Winery
4.5 star property
19.6 km from Windsor Ski Lift
9.8 out of 10, Exceptional, (19 reviews)
"Stunning scenery, great wine and food. Friendly, helpful people on site and the hot tub is blissfully perfect ❤️"
United States
Christine
The price is SAR 482
SAR 1,547 total
includes taxes & fees
25 Nov - 26 Nov
Paschal Winery
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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
A sign for Prospero's Flagship Inn with a star emblem and a pedestrian crossing sign nearby.
Prospero's Flagship Inn
2.5 star property
8.4
Very good
1,496 reviews
View
A hotel entrance with outdoor seating, potted plants, and a well-lit facade.
Comfort Inn & Suites Ashland
2.5 star property
9.0
Wonderful
1,069 reviews
View
Exterior
Best Western Windsor Inn
2.5 star property
9.0
Wonderful
1,000 reviews
View
Exterior
Callahan's Mountain Lodge
3.0 star property
8.8
Excellent
1,124 reviews
View
A Holiday Inn Express hotel with a two-story structure, a parking lot, and a landscaped area with shrubs and a tall tree.
Holiday Inn Express & Suites Ashland by IHG
2.5 star property
9.2
Wonderful
1,001 reviews
View

Top Windsor Ski Lift Hotel Reviews

Stratford Inn

Stratford Inn

10/10 Excellent
"I was very pleased with this hotel! Great location, super friendly staff, good breakfast buffet…I would definitely return here!"
Irene 2-night trip
Posted 3 hours ago
Stratford Inn

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

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.