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Check prices for these dates

Tonight
7 Nov - 8 Nov
Tomorrow
8 Nov - 9 Nov
Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

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Our top choices for Windsor Ski Lift hotels

A Holiday Inn Express hotel with a two-story structure, a parking lot, and a landscaped area with shrubs and a tall tree.

1. 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
9.4 out of 10, Exceptional, (1,006 reviews)
"Very friendly staff."
Canada
Tanis
The price is Rp1.664.188
Rp1.855.569 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Ashland by IHG
An indoor swimming pool with clear water, tiled edges, and a blue mosaic border. There are lounge chairs and potted plants near the windows.

2. Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District, 12.1 km from Windsor Ski Lift
9.4 out of 10, Exceptional, (1,796 reviews)
"Nice little hotel that was well decorated for the holiday."
United States
Thomas
The price is Rp1.690.417
Rp1.884.815 total
includes taxes & fees
10 Nov - 11 Nov
Stratford Inn
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, (1,001 reviews)
"Great location, clean room, friendly staff"
United States
Ross
The price is Rp2.034.406
Rp2.268.364 total
includes taxes & fees
20 Nov - 21 Nov
Best Western Windsor Inn
A hotel entrance with outdoor seating, potted plants, and a well-lit facade.

4. 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, (1,068 reviews)
"Clean rooms, good breakfast, conveniently located."
United States
Bill
The price is Rp1.752.824
Rp1.779.116 total
includes taxes & fees
6 Dec - 7 Dec
Comfort Inn & Suites Ashland
A spacious lobby with a large wooden floor, a green peace sign decoration, and a large window offering a view of the outdoors.

5. 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, (1,577 reviews)
"Great hotel!"
United States
Nicholas
The price is Rp1.774.531
Rp2.159.465 total
includes taxes & fees
12 Nov - 13 Nov
Ashland Hills Hotel & Suites
A swimming pool with a clear view of the poolside area, including lounge chairs and a covered seating area.

6. 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, (1,004 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 Rp1.236.809
Rp1.379.042 total
includes taxes & fees
20 Nov - 21 Nov
Timbers INN and Suites
Exterior

7. 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, (1,128 reviews)
"Cozy getaway. Loved our stay here."
United States
Cameron
The price is Rp1.741.971
Rp2.039.354 total
includes taxes & fees
4 Dec - 5 Dec
Callahan's Mountain Lodge
An outdoor dining area with a table set for two, surrounded by chairs, a red umbrella, and a stone water feature.

8. 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, (1,007 reviews)
"Very nicece hotel and perfect location for walking and exploring Ashland."
United States
Heather
The price is Rp2.100.133
Rp2.341.621 total
includes taxes & fees
8 Nov - 9 Nov
Plaza Inn & Suites at Ashland Creek
A sign for Prospero's Flagship Inn with a star emblem and a pedestrian crossing sign nearby.

9. 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, (1,491 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 Rp1.286.128
Rp1.434.096 total
includes taxes & fees
8 Nov - 9 Nov
Prospero's Flagship Inn
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

Lithia Springs Resort
3.0 star property
15.4 km from Windsor Ski Lift
9.4 out of 10, Exceptional, (1,010 reviews)
"Well maintained, affordable delicious breakfast, clean rooms"
United States
Christina
The price is Rp1.692.754
Rp2.079.925 total
includes taxes & fees
16 Nov - 17 Nov
Lithia Springs Resort
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 Rp1.285.630
Rp1.433.477 total
includes taxes & fees
8 Dec - 9 Dec
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 Rp1.718.636
Rp1.916.349 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, (1,011 reviews)
"Cutest hotel ever! Will stay again."
Canada
Tamara
The price is Rp1.692.754
Rp2.168.403 total
includes taxes & fees
1 Dec - 2 Dec
Ashland Springs Hotel
A large, two-story house with a wrap-around porch and a steeply pitched roof.

14. Winchester Inn

Winchester Inn
3.5 star property
Historic Downtown District, 12.3 km from Windsor Ski Lift
9.6 out of 10, Exceptional, (291 reviews)
"Amazing breakfasts, friendly staff, best location"
United States
Ellen
The price is Rp2.352.579
Rp2.908.931 total
includes taxes & fees
9 Nov - 10 Nov
Winchester Inn
A garden pathway with wisteria and red flowers, surrounded by lush greenery.

15. Arden Forest Inn

Arden Forest Inn
4.0 star property
13.3 km from Windsor Ski Lift
9.8 out of 10, Exceptional, (115 reviews)
"Tasteful charming bedroom and bathroom."
United States
Jean
The price is Rp2.474.575
Rp2.759.152 total
includes taxes & fees
8 Nov - 9 Nov
Arden Forest Inn
A Victorian-style building with ornate architectural details, large windows, and a red door.

16. 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 Rp3.124.570
Rp3.483.895 total
includes taxes & fees
8 Dec - 9 Dec
McCall House Boutique Inn
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 Rp3.436.910
Rp3.832.155 total
includes taxes & fees
8 Nov - 9 Nov
Abigail’s Bed & Breakfast Inn
A hotel room with a desk, laptop, two beds, and a round mirror.

18. 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 Rp1.291.236
Rp1.439.689 total
includes taxes & fees
20 Nov - 21 Nov
Ashland Motel - Oregon
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a covered seating area.

19. 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 Rp3.671.705
Rp4.093.902 total
includes taxes & fees
8 Nov - 9 Nov
Palm Cottages
A hotel room with a bed, bedside tables, a desk, a chair, a dresser, and a painting on the wall.

20. Baymont by Wyndham

Baymont by Wyndham
2.5 star property
11.7 km from Windsor Ski Lift
7.8 out of 10, Good, (708 reviews)
"Location is great."
United States
Brian
The price is Rp1.627.380
Rp1.814.529 total
includes taxes & fees
20 Nov - 21 Nov
Baymont by Wyndham
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.
View all properties

Compare popular hotels close to Windsor Ski Lift

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
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
9.4
Exceptional
1,006 reviews
View
An indoor swimming pool with clear water, tiled edges, and a blue mosaic border. There are lounge chairs and potted plants near the windows.
Stratford Inn
2.5 star property
9.4
Exceptional
1,796 reviews
View
Exterior
Best Western Windsor Inn
2.5 star property
9.0
Wonderful
1,001 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
1,068 reviews
View
A spacious lobby with a large wooden floor, a green peace sign decoration, and a large window offering a view of the outdoors.
Ashland Hills Hotel & Suites
3.0 star property
8.8
Excellent
1,577 reviews
View

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

Top Windsor Ski Lift Hotel Reviews

A two-story building with a wooden facade, large windows, and a front porch with chairs.
The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges
Historic Railroad District

10/10 Excellent

This is a very differant and rare hotel. If you want something very different fr0m the chain hotel give it a go.
United Kingdom
christopher
Reviewed July 15, 2025
The Peerless Hotel by WanderLodges

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 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.