Title: Book the Best Windsor Hills WINERY Hotels in 2026 | Expedia.ca

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![Orlando, Florida. July 22, 2019 Orlando gold lettering on black background. Vector with travel icons and fireworks. Travel Postcard](https://images.trvl-media.com/place/553248635976007891/461aeb04-6833-4510-8c6a-0a6593b71d02.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/553248635976007891/461aeb04-6833-4510-8c6a-0a6593b71d02.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Windsor Hills Winery Hotels

Tonight

[Feb 2 - Feb 3](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2026-02-02&endDate=2026-02-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 3 - Feb 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2026-02-03&endDate=2026-02-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windsor Hills hotels with winery

![A heated pool](https://images.trvl-media.com/lodging/84000000/83920000/83911700/83911612/ed992b85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/84000000/83920000/83911700/83911612/443703ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83920000/83911700/83911612/w2818h1895x0y0-43bb7f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/84000000/83920000/83911700/83911612/786c0eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fully Renovated w Heated pool, 3 miles from Disney

[](https://www.expedia.ca/Orlando-Hotels-Steps-From-Disney-Beautiful-5-BD5-BR-Villa-Fully-Renovated-W-Heated-Poolspa.h83911612.Hotel-Information)

Windsor Hills

10/10

Exceptional

(26 reviews)

"Great stay."

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

Holly S.

CA $352

CA $829 total

includes taxes & fees

Feb 5 - Feb 6

[](https://www.expedia.ca/Orlando-Hotels-Steps-From-Disney-Beautiful-5-BD5-BR-Villa-Fully-Renovated-W-Heated-Poolspa.h83911612.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/08ef9167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/ccd30aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Non Smoking | Living area](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/91ca61e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/w3837h2557x0y0-c7800382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home2 Suites by Hilton Orlando at Flamingo Crossings

[](https://www.expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.Hotel-Information)

Bay Lake

9.2/10

Wonderful

(5,228 reviews)

"great place to stay nearest to all location ."

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

VIMAL

CA $154

CA $173 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236661/f518be97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236661/07be24f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236661/cf14f0e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236661/f7e25bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home2 Suites By Hilton Winter Garden

[](https://www.expedia.ca/Winter-Garden-Hotels-Home2-Suites-By-Hilton-Winter-Garden.h102236661.Hotel-Information)

Winter Garden

9.4/10

Exceptional

(388 reviews)

"Great service, clean room, comfortable beds"

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

Scarlett

CA $200

CA $225 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Winter-Garden-Hotels-Home2-Suites-By-Hilton-Winter-Garden.h102236661.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/1000000/290000/281600/281522/b9a5f9be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/290000/281600/281522/5ff401aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/290000/281600/281522/7d2d1e3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/290000/281600/281522/271998df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Homewood Suites by Hilton Orlando-International Drive/Convention Center

[](https://www.expedia.ca/Orlando-Hotels-Homewood-Suites-By-Hilton-Orlando-Intl-DriveConvention-Ctr.h281522.Hotel-Information)

International Drive District

8.4/10

Very good

(1,006 reviews)

"Great stay "

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

Malik

CA $133

CA $149 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Orlando-Hotels-Homewood-Suites-By-Hilton-Orlando-Intl-DriveConvention-Ctr.h281522.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/b5aeb802.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/04d5c0c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/25aafbc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/3ed7040c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family-Friendly Cottage Near Orlando’s Top Attractions

[](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.Hotel-Information)

Kissimmee

10/10

Exceptional

(1 review)

"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"

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

Joyce R.

CA $123

CA $276 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.Hotel-Information)

![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/113000000/112590000/112587300/112587236/e3c12941.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112590000/112587300/112587236/3781c41e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112590000/112587300/112587236/2da4d42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112590000/112587300/112587236/d8435983.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW Enchanted Escape in Storey Lake, Dogs OK

[](https://www.expedia.ca/Orlando-Hotels-New-Enchanted-Escape-In-Storey-Lake.h112587236.Hotel-Information)

Kissimmee

10/10

Exceptional

(1 review)

"Beautiful spacious place for a decent size family little water park is great for young kids"

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

Madison B.

CA $139

CA $868 total

includes taxes & fees

Feb 5 - Feb 6

[](https://www.expedia.ca/Orlando-Hotels-New-Enchanted-Escape-In-Storey-Lake.h112587236.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/101000000/100940000/100935900/100935858/9def0990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/101000000/100940000/100935900/100935858/50bdd69b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100940000/100935900/100935858/e45b93b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100940000/100935900/100935858/6537c23c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Lake Front Cottage

[](https://www.expedia.ca/Clermont-Hotels-Cozy-Lake-Front-Cottage.h100935858.Hotel-Information)

Clermont

10/10

Exceptional

(19 reviews)

"Will definitely be staying again"

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

Tom W.

CA $164

CA $331 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Clermont-Hotels-Cozy-Lake-Front-Cottage.h100935858.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/89000000/88630000/88620200/88620137/cdfa9189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88630000/88620200/88620137/fb7e6682.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/89000000/88630000/88620200/88620137/cafc8fc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88630000/88620200/88620137/6f3b1622.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Orlando Oasis: Exclusive Villa Close to Disney

[](https://www.expedia.ca/Orlando-Hotels-Brand-New-8BR-6BA-With-Heated-Pool-Spa-Near-Disney.h88620137.Hotel-Information)

Davenport

9.2/10

Wonderful

(55 reviews)

"Quick check in, beautiful property, clean, wonderful pool and hot tub. Everything looked amazing. "

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

Kellee H.

[](https://www.expedia.ca/Orlando-Hotels-Brand-New-8BR-6BA-With-Heated-Pool-Spa-Near-Disney.h88620137.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/103000000/102190000/102188800/102188751/219d21d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, table tennis](https://images.trvl-media.com/lodging/103000000/102190000/102188800/102188751/a81a8721.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, table tennis](https://images.trvl-media.com/lodging/103000000/102190000/102188800/102188751/1d04bf14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102190000/102188800/102188751/w834h683x95y0-6d36f719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Minutes to Disney - The Magical Family Villa

[](https://www.expedia.ca/Orlando-Hotels-Exclusive-Pool-Home-10-Minutes-To-Disney.h102188751.Hotel-Information)

Kissimmee

10/10

Exceptional

(18 reviews)

"Wonderful place and very convenient for visiting Disney. Host was amazing and quick to respond to answer any questions."

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

Lindsay D.

CA $146

CA $489 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Orlando-Hotels-Exclusive-Pool-Home-10-Minutes-To-Disney.h102188751.Hotel-Information)

![LCD TV, video-game console, DVD player](https://images.trvl-media.com/lodging/38000000/37250000/37242400/37242341/1a534817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/38000000/37250000/37242400/37242341/72359bae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/38000000/37250000/37242400/37242341/08866688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37250000/37242400/37242341/58899e81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ✦Comfortable and Cozy Home✦Coral Cay Resort and Nearby Disney✦

[](https://www.expedia.ca/Orlando-Hotels-Comfortable-And-Cozy-Homecoral-Cay-Resort-And-Nearby-Disney.h37242341.Hotel-Information)

Kissimmee

10/10

Exceptional

(2 reviews)

"The home was absolutely lovely. I have no complaints whatsoever…we loved it and enjoyed our stay."

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

Brashawnda F.

CA $114

CA $460 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Orlando-Hotels-Comfortable-And-Cozy-Homecoral-Cay-Resort-And-Nearby-Disney.h37242341.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=2026-02-16&endDate=2026-02-17&regionId=553248635976007891&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

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