Title: Book the Best Windsor Hills Ski Hotels in 2026 from CA $445 | Expedia.ca

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# Find Ski Hotels in Windsor Hills, FL from CA $445

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## Check availability on Windsor Hills Ski Hotels

Tonight

[Dec 30 - Dec 31](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2025-12-30&endDate=2025-12-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 31 - Jan 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2025-12-31&endDate=2026-01-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windsor Hills ski hotels

![Villa (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350017/55db005a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350017/5b1f3224.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350017/df86f858.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350017/1d8668d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lake Berkley Villas Swanky

[](https://www.expedia.ca/Orlando-Hotels-4701-Lake-Berkley-Villa-Renovated-3-Bed.h119350017.Hotel-Information)

Lake Berkley

CA $169

CA $445 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Orlando-Hotels-4701-Lake-Berkley-Villa-Renovated-3-Bed.h119350017.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/120000000/119060000/119056100/119056029/cb0660eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/120000000/119060000/119056100/119056029/de8816dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119060000/119056100/119056029/66971208.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![8 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119060000/119056100/119056029/8afae90c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Unforgettable 8BR Oasis in ChampionsGate – Game Room, Home Theater, Near Disney!

[](https://www.expedia.ca/Orlando-Hotels-Peaceful-8-Bedroom-House-With-AC-In-Lovely-Davenport.h119056029.Hotel-Information)

Champions Gate

10/10

Exceptional

(1)

"We loved the house! It's perfect for who is travelling with teens and kids. The pool, the game room, everything was spotless! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Pietra A.

CA $149

CA $828 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Orlando-Hotels-Peaceful-8-Bedroom-House-With-AC-In-Lovely-Davenport.h119056029.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/120000000/119060000/119056100/119056024/e79e2dd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119060000/119056100/119056024/55d3c0c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119060000/119056100/119056024/f205be31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119060000/119056100/119056024/77b2a311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Majestic 8BR Oasis in ChampionsGate – Game Room, Home Theater, Near Disney!

[](https://www.expedia.ca/Orlando-Hotels-Spacious-8-Bedroom-House-In-Fabulous-Four-Corners-With-AC.h119056024.Hotel-Information)

Champions Gate

8.8/10

Excellent

(3)

"The host was very responsive and very fast to answer all questions. Very nice home especially if you have a large family. The beds were very comfortable and the home was very clean. Highly recomend this host and this property. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Doug B.

CA $149

CA $837 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Orlando-Hotels-Spacious-8-Bedroom-House-In-Fabulous-Four-Corners-With-AC.h119056024.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/20000000/19940000/19938600/19938534/6e739c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/20000000/19940000/19938600/19938534/62e4b14b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19940000/19938600/19938534/46649cae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19940000/19938600/19938534/6ec94f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxurious 5\*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning

[](https://www.expedia.ca/Orlando-Hotels-Luxurious-5Executive-3Br-Villa-Vista-CayPool-Enhanced-Cleaning.h19938534.Hotel-Information)

Orlando

9.6/10

Exceptional

(44)

"Too short of a stay but enjoyed every moment. The rental was emaculant. The best by far since staying at Vista Cay. The owner was great. She kept in touch and up to date with each detail of our stay including our welcoming text as well as thanking us for staying at her location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Vediarshar B.

CA $282

CA $1,210 total

includes taxes & fees

Jan 3 - Jan 4, 2026

[](https://www.expedia.ca/Orlando-Hotels-Luxurious-5Executive-3Br-Villa-Vista-CayPool-Enhanced-Cleaning.h19938534.Hotel-Information)

![Smart TV, video games, foosball, offices](https://images.trvl-media.com/lodging/91000000/90090000/90088700/90088606/f0240059.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/91000000/90090000/90088700/90088606/2c30710a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90090000/90088700/90088606/de5a4821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90090000/90088700/90088606/3462a8fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### King Bed Suite, Fireside Hot Tub, Gameroom

[](https://www.expedia.ca/Auburndale-Hotels-King-Bed-Suite.h90088606.Hotel-Information)

Auburndale

10/10

Exceptional

(2)

"Clean, nice house, great amenities. I’d stay again"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jason C.

CA $384

CA $820 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Auburndale-Hotels-King-Bed-Suite.h90088606.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/114000000/113750000/113741000/113740977/f825e9b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113750000/113741000/113740977/e447efa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113750000/113741000/113740977/19746081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113750000/113741000/113740977/95aa4a5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 4862-303 Fresh & Modern 3-BD Condo at Vista Cay

[](https://www.expedia.ca/Orlando-Hotels-4862-303-Fresh-Modern-3-BD-Condo-At-Vista-Cay.h113740977.Hotel-Information)

Orlando

10/10

Exceptional

(1)

"Super clean. Easy in and easy out. Everything we needed was there."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Linda M.

CA $354

CA $729 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Orlando-Hotels-4862-303-Fresh-Modern-3-BD-Condo-At-Vista-Cay.h113740977.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/106000000/105320000/105317300/105317246/4b63563b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/106000000/105320000/105317300/105317246/b8a8dfcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball](https://images.trvl-media.com/lodging/106000000/105320000/105317300/105317246/0e1f923a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball](https://images.trvl-media.com/lodging/106000000/105320000/105317300/105317246/ff527104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 8102 Vacation getaway at Windsor

[](https://www.expedia.ca/Orlando-Hotels-8102-Vacation-Getaway-At-Windsor.h105317246.Hotel-Information)

Kissimmee

10/10

Exceptional

(2)

"Great communication with management, Clean and very bright have booked again. Great job"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Terry L.

CA $339

CA $706 total

includes taxes & fees

Jan 15 - Jan 16, 2026

[](https://www.expedia.ca/Orlando-Hotels-8102-Vacation-Getaway-At-Windsor.h105317246.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106570000/106568900/106568850/c47c2c0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/107000000/106570000/106568900/106568850/219c1970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106570000/106568900/106568850/w2048h1533x0y3-e5ca09ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106570000/106568900/106568850/68aec328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2723 Indulging 2/2 Condo near Disney

[](https://www.expedia.ca/Orlando-Hotels-2723-Indulging-22-Condo-Near-Disney.h106568850.Hotel-Information)

Kissimmee

10/10

Exceptional

(1)

"I am truly a satisfied customer. Everything was clean/neat when I arrived. There was a cozy environment when entering the home. The location is close to Walmart, shopping areas, and restaurants. This is a safe gated community and very quiet. I would definitely recommend."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Monique C.

CA $405

CA $810 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Orlando-Hotels-2723-Indulging-22-Condo-Near-Disney.h106568850.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/114000000/113710000/113702300/113702240/c8ccb9f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/114000000/113710000/113702300/113702240/8f5a93c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/114000000/113710000/113702300/113702240/cd204991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113710000/113702300/113702240/w1200h797x0y3-f59a0a58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1307 Cozy Studio Retreat at Regal Palms Resort

[](https://www.expedia.ca/Orlando-Hotels-1307-Cozy-Studio-Retreat-At-Regal-Palms-Resort.h113702240.Hotel-Information)

Regal Palms

CA $224

CA $450 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Orlando-Hotels-1307-Cozy-Studio-Retreat-At-Regal-Palms-Resort.h113702240.Hotel-Information)

![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/105000000/104290000/104280400/104280316/w1184h942x8y6-963d211a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/105000000/104290000/104280400/104280316/e4720b55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/105000000/104290000/104280400/104280316/c03d2b5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/105000000/104290000/104280400/104280316/4448f252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1802 Cozy Condo 3 min Universal

[](https://www.expedia.ca/Orlando-Hotels-6165-Cozy-Condo-3-Min-Universal.h104280316.Hotel-Information)

International Drive District

8.0/10

Very good

(2)

"Perfect location to stay for any Orlando activities. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

cristian v.

CA $339

CA $625 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Orlando-Hotels-6165-Cozy-Condo-3-Min-Universal.h104280316.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2026-01-13&endDate=2026-01-14&regionId=553248635976007891&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true)

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