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Check prices for these dates

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16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
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26 Dec - 28 Dec

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Our top choices for Windsor Ski Lift hotels

Exterior
Holiday Inn Express & Suites Ashland by IHG

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, (1006)
"Very nice property with nice decor. Room much nicer than competitors I’ve stayed with . Extremely clean, super staff. Will stay here again!"
United States
Christopher
The price is ฿3,272
฿3,648 total
includes taxes & fees
16 Jan - 17 Jan 2026
Holiday Inn Express & Suites Ashland by IHG
Front of property
Flagship Inn of Ashland

Flagship Inn of Ashland

Flagship Inn of Ashland
2.5 star property
11.4 km from Windsor Ski Lift
8.8 out of 10, Excellent, (1193)
"Huge room Great check in Very comfortable My 5th stay here "
United States
Michael L
The price is ฿1,983
฿2,211 total
includes taxes & fees
19 Dec - 20 Dec
Flagship Inn of Ashland
Seasonal outdoor pool, open 7:00 AM to 8:00 PM, pool umbrellas
Country Willows Inn and Estate

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, (33)
"Beautiful setting close to downtown. Pool is marvelous!"
United States
Carol
Country Willows Inn and Estate
Lobby sitting area
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
3.0 star property
11.8 km from Windsor Ski Lift
9.0 out of 10, Wonderful, (1499)
"A very great stay with our two dogs！"
United States
Yaolin
The price is ฿2,821
฿3,498 total
includes taxes & fees
1 Jan - 2 Jan 2026
Ashland Hills Hotel & Suites
Indoor spa tub
Stratford Inn

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, (1599)
"Clean room, attentive staff, easy walk to downtown. "
United States
Richard
The price is ฿2,833
฿3,159 total
includes taxes & fees
21 Dec - 22 Dec
Stratford Inn
Seasonal outdoor pool
Timbers INN and Suites

Timbers INN and Suites

Timbers INN and Suites
2.0 star property
11.3 km from Windsor Ski Lift
8.6 out of 10, Excellent, (1002)
"Room very good and vintage 70s style. "
United States
James P
The price is ฿1,954
฿2,178 total
includes taxes & fees
31 Dec - 1 Jan 2026
Timbers INN and Suites
Garden
Ashland Springs Hotel

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, (1006)
"Small room but wonderful view and comfortable bed. "
United States
Jessica
The price is ฿3,013
฿3,832 total
includes taxes & fees
18 Dec - 19 Dec
Ashland Springs Hotel
Exterior
Best Western Windsor Inn

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, (1003)
"Friendly staff and very clean"
United States
Noel
The price is ฿3,429
฿3,824 total
includes taxes & fees
16 Jan - 17 Jan 2026
Best Western Windsor Inn
Interior detail
Relax Inn At Ashland

Relax Inn At Ashland

Relax Inn At Ashland
1.5 star property
11.7 km from Windsor Ski Lift
6.8 out of 10, (495)
"Great family owned experience "
United States
Aliesje
The price is ฿1,840
฿2,052 total
includes taxes & fees
18 Dec - 19 Dec
Relax Inn At Ashland
Front of property
Winchester Inn

Winchester Inn

Winchester Inn
3.5 star property
Historic Downtown District, 12.3 km from Windsor Ski Lift
9.8 out of 10, Exceptional, (261)
"Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!"
United States
Laura
The price is ฿5,631
฿6,656 total
includes taxes & fees
4 Jan - 5 Jan 2026
Winchester Inn
Terrace/patio
The Peerless Hotel by WanderLodges

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, (95)
"A lovely spot to stay! Our room was beautifully furnished and cozy with a historic charm. The outdoor balcony was a great way to wake up with a cup of coffee. Within walking distance of the theaters and downtown. "
United States
Matthew
The Peerless Hotel by WanderLodges
Outdoor dining
Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek
3.0 star property
12.9 km from Windsor Ski Lift
8.8 out of 10, Excellent, (1003)
"Nice stay again in Ashland amazing location for food and shopping! Love the local vibe. Comfortable bed and simple breakfast to start the day off right! "
United States
Brian
Plaza Inn & Suites at Ashland Creek
Seasonal outdoor pool
Palm Cottages

Palm Cottages

Palm Cottages
2.5 star property
11.6 km from Windsor Ski Lift
9.2 out of 10, Wonderful, (211)
"The room was not only spotless, but unique and very charming decor. It is like a little house and I wanted to stay another night just to enjoy reading in the little window nook!"
United States
Jennifer
The price is ฿4,781
฿5,331 total
includes taxes & fees
18 Dec - 19 Dec
Palm Cottages
Terrace/patio
A Cowslip's Belle Inn

A Cowslip's Belle Inn

A Cowslip's Belle Inn
3.0 star property
12.9 km from Windsor Ski Lift
9.8 out of 10, Exceptional, (40)
"Lovely yard courtyard area with koi pond"
United States
Paul
The price is ฿4,247
฿6,489 total
includes taxes & fees
31 Dec - 1 Jan 2026
A Cowslip's Belle Inn
Lobby
The Bard's Inn, BW Signature Collection by Best Western

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
8.6 out of 10, Excellent, (1010)
"The Bards Inn is lovely with each room themed after a Shakespe Play. Location is excellent just at the top of Main St. I can highly recommend this hotel"
United States
Suzanne
The price is ฿3,304
฿3,684 total
includes taxes & fees
16 Jan - 17 Jan 2026
The Bard's Inn, BW Signature Collection by Best Western
Front of property
Ashland Commons Hostel

Ashland Commons Hostel

Ashland Commons Hostel
2.0 star property
12.9 km from Windsor Ski Lift
9.4 out of 10, Exceptional, (50)
"Nice hostel and clean rooms"
United States
EASWARAMOORTHI
The price is ฿1,218
฿2,620 total
includes taxes & fees
26 Dec - 27 Dec
Ashland Commons Hostel
Front of property
McCall House Boutique Inn

McCall House Boutique Inn

McCall House Boutique Inn
4.0 star property
Historic Downtown District, 12.6 km from Windsor Ski Lift
9.2 out of 10, Wonderful, (579)
"The room was very clean, meals were excellent. Staff was excellent."
United States
Renae
McCall House Boutique Inn
Two Queen Room - Non Smoking (No Pets Allowed) | Egyptian cotton sheets, desk, free WiFi, bed sheets
Ashland Motel - Oregon

Ashland Motel - Oregon

Ashland Motel - Oregon
2.0 star property
11.5 km from Windsor Ski Lift
7.8 out of 10, Good, (216)
"Great service "
United States
James
The price is ฿2,171
฿2,420 total
includes taxes & fees
18 Dec - 19 Dec
Ashland Motel - Oregon
Room, 2 Queen Beds, Non Smoking | Desk, blackout curtains, iron/ironing board, free WiFi
Scottish Inn

Scottish Inn

Scottish Inn
2.5 star property
11.7 km from Windsor Ski Lift
7.8 out of 10, Good, (666)
"Easy parking. Convenient to downtown and shopping"
United States
Michael
The price is ฿2,265
฿2,526 total
includes taxes & fees
21 Dec - 22 Dec
Scottish Inn
Exterior
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
2.5 star property
15.9 km from Windsor Ski Lift
8.8 out of 10, Excellent, (1006)
"Staff was excellent and very nice and room was clean and location is good Town is very cool 👍"
United States
Thomas
The price is ฿2,628
฿2,667 total
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Inn & Suites Ashland
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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Top Windsor Ski Lift Hotel Reviews

Cedarwood Inn of Ashland

Cedarwood Inn of Ashland

10/10 Excellent
"We’ve stayed here twice. Nice place for reasonable price."
Mai 1-night trip
Posted 1 month ago
Cedarwood Inn of Ashland

Hotels near other Windsor Ski Lift attractions

Mount Ashland Ski Area

4.2/5 (136 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

You can take time to visit Comer Ski Lift during your travels to Ashland. Discover the top-notch restaurants and entertainment choices in this family-friendly 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 321 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 Flagship Inn of Ashland 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 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.