Title: Winter Park Vacation Packages & Trips 2026 from CA $581 | Expedia.ca

[Hotels in Winter Park](https://expedia.ca/Winter-Park-Hotels.d7902.Travel-Guide-Hotels)[Vacation Rentals in Winter Park](https://expedia.ca/Winter-Park-Vacation-Rentals.d7902.Travel-Guide-VacationRentals)[Flights to Winter Park](https://expedia.ca/Cheap-Flights-To-Winter-Park.d7902.Travel-Guide-Flights)[Winter Park Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Park.d7902.Car-Rental-Guide)

![](https://images.trvl-media.com/place/553248621532654331/8b41338a-0cb1-4ae5-88e7-e7e2529bfeaa.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Winter Park Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

#### Your Winter Park Vacation

When a getaway to the city is calling, answer it with a Winter Park vacation package. The neighborhood of Ivanhoe Village, which is great for dining, bars and pubs and shopping, makes a fantastic base for your adventures. [Rollins College](https://www.expedia.ca/Rollins-College-Orlando.d6154361.Vacation-Attraction), [Full Sail University](https://www.expedia.ca/Full-Sail-University-Orlando.d6154770.Vacation-Attraction) and [Altamonte Mall](https://www.expedia.ca/Altamonte-Mall-Orlando.d6128112.Vacation-Attraction) are just a few of the attractions worth exploring during your trip to Winter Park. Stop daydreaming and start adventuring. Check out the many options on Expedia today and put your Winter Park vacation plans in motion!

## Top Winter Park Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Palazzo Lakeside Hotel](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/de0795f9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Palazzo Lakeside Hotel

CA $581

per person

Apr 15 - Apr 19

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Orlando (MCO)

8.2/10 Very Good! (5,145 reviews)

Clean and quiet! Staff was great

Reviewed on Feb 1, 2026

![Westgate Vacation Villas Resort](https://images.trvl-media.com/lodging/1000000/100000/99000/98920/b8afec09_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Westgate Vacation Villas Resort

CA $671

per person

Apr 6 - Apr 13

found 1 day ago

Roundtrip flight included

Ottawa (YOW) to Orlando (MCO)

8/10 Very Good! (1,703 reviews)

Everything was good

Reviewed on Jan 24, 2026

![Westgate Town Center Resort](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/410a3d83_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Westgate Town Center Resort

CA $733

per person

Mar 8 - Mar 15

found 10 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Orlando (MCO)

8/10 Very Good! (1,367 reviews)

Clean and comfortable. Especially the bed. We didn't get up with sore hips from a hard matress.

Reviewed on Feb 2, 2026

![Westgate Towers Resort](https://images.trvl-media.com/lodging/1000000/180000/170900/170878/bd08ea58_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Westgate Towers Resort

CA $627

per person

Apr 13 - Apr 20

found 17 hours ago

Roundtrip flight included

Toronto (YYZ) to Orlando (MCO)

8.6/10 Excellent! (1,002 reviews)

Room was perfect for me & my family as we had the 2 bedroom suite.

Reviewed on Feb 1, 2026

![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/86e77c07_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Westgate Lakes Resort & Spa Universal Studios Area

CA $706

per person

Mar 25 - Mar 30

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Orlando (MCO)

8.2/10 Very Good! (5,482 reviews)

A great place to stay. The room was immaculate, it even came with a in room washer and dryer and a dishwasher.

Reviewed on Feb 1, 2026

## Ready to book your vacation to Winter Park?

Choose your dates

## Winter Park Hotel Deals

![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

Fully refundableReserve now, pay when you stay

CA $157

CA $176 total

Feb 26 - Feb 27

includes taxes & fees

9.2/10 Wonderful! (4,432 reviews)

We only stayed one night but villa was huge clean and very nice

Reviewed on Jan 27, 2026

[](https://expedia.ca/Hotel-Search?startDate=26%2F02%2F2026&endDate=27%2F02%2F2026&selected=23110&PinnedHotelID=23110&HadPinnedHotel=true&regionId=7902)

![Rosen Inn at Pointe Orlando](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Rosen Inn at Pointe Orlando

9000 International Drive Orlando FL

Fully refundableReserve now, pay when you stay

CA $100

CA $113 total

Feb 21 - Feb 22

includes taxes & fees

8.4/10 Very Good! (5,664 reviews)

Good basic place.

Reviewed on Jan 30, 2026

[](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=8892&PinnedHotelID=8892&HadPinnedHotel=true&regionId=7902)

![DoubleTree by Hilton Hotel Orlando at SeaWorld](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

DoubleTree by Hilton Hotel Orlando at SeaWorld

10100 International Drive Orlando FL

Fully refundableReserve now, pay when you stay

CA $109

CA $161 total

Feb 22 - Feb 23

includes taxes & fees

7.4/10 Good! (6,478 reviews)

Friendly staff, room very clean

Reviewed on Jan 28, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=18874&PinnedHotelID=18874&HadPinnedHotel=true&regionId=7902)

[See all 14,881 properties in Winter Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F02%2F2026&endDate=04%2F02%2F2026&regionId=7902)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Winter Park

![Walt Disney World® Resort](https://images.trvl-media.com/place/6034120/a6e2fb5b-4859-4b13-8673-5364decc02ec.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Walt Disney World® Resort

Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.

[](https://expedia.ca/Walt-Disney-World-Resort-Orlando.d6034120.Vacation-Attraction)

![Universal Studios Florida™](https://images.trvl-media.com/place/6049239/81061cd5-1210-4715-a806-d6865f85e0b2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Universal Studios Florida

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

[](https://expedia.ca/Universal-Studios-Florida-Florida-Center.d6049239.Vacation-Attraction)

![Universal Studios Orlando which includes street scenes, a city and rides](https://images.trvl-media.com/place/6049239/75d545e9-4a50-4b21-9fd2-665c3f6b014f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Universal Orlando Resort

Make your Florida vacation one to remember with a stay at this hotel and theme park complex.

[](https://expedia.ca/Universal-Orlando-Resort-Florida-Center.d6347698.Vacation-Attraction)

### What to do in Winter Park

![Universal Orlando Resort Theme Park Tickets](https://mediaim.expedia.com/localexpert/449578/292355e4-a5b6-4251-bddb-ccea0177846f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Universal Orlando Resort Theme Park Tickets (US & Canada)

CA $209

per adult

**86%** of travellers recommend

[](https://expedia.ca/things-to-do/universal-orlando-resort-theme-park-tickets-us-canada.a449578.activity-details)

![Aquatica Orlando](https://mediaim.expedia.com/localexpert/407892/33b09fce-abbf-446b-bce5-738d4c15128d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Aquatica Orlando

CA $73

per traveller

**84%** of travellers recommend

[](https://expedia.ca/things-to-do/aquatica-orlando.a407892.activity-details)

![I-RIDE Trolley Pass](https://mediaim.expedia.com/localexpert/5000146/6e49b2db-95e1-4f7b-bc36-27398dd0c4a7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### I-RIDE Trolley Pass

CA $15

per traveller

**86%** of travellers recommend

[](https://expedia.ca/things-to-do/i-ride-trolley-pass.a5000146.activity-details)

[See all activities in Winter Park](https://expedia.ca/things-to-do/search?rid=7902)

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- [Visit Orwin Manor ](https://www.expedia.ca/Orlando-Orwin-Manor.dx553248635976471367)
- [Orlando Science Center ](https://www.expedia.ca/Orlando-Science-Center-Ivanhoe-Village.d6069353.Vacation-Attraction)
- [Orlando Vacations ](https://www.expedia.ca/Orlando.d178294.Destination-Travel-Guides)
- [Princeton Park ](https://www.expedia.ca/Princeton-Park-College-Park.d553248621563220217.Vacation-Attraction)
- [Red Bug Lake Park ](https://www.expedia.ca/Red-Bug-Lake-Park-Casselberry.d553248634983923992.Vacation-Attraction)
- [Rollins Museum of Art ](https://www.expedia.ca/Rollins-Museum-Of-Art-Orlando.d6154782.Vacation-Attraction)
- [St. James Cathedral ](https://www.expedia.ca/St-James-Cathedral-Downtown-Orlando.d6154346.Vacation-Attraction)
- [The Plaza Theatre ](https://www.expedia.ca/The-Plaza-Theatre-Colonial-Town-Center.d6154904.Vacation-Attraction)
- [Village Plaza Shopping Center ](https://www.expedia.ca/Village-Plaza-Shopping-Center-Orlando.d553248621558036314.Vacation-Attraction)
- [Walt Disney World® Resort ](https://www.expedia.ca/Walt-Disney-World-Resort-Orlando.d6034120.Vacation-Attraction)
- [Winter Pines Golf Club ](https://www.expedia.ca/Winter-Pines-Golf-Club-Orlando.d6239892.Vacation-Attraction)
- [Zora Neale Hurston National Museum of Fine Arts ](https://www.expedia.ca/Zora-Neale-Hurston-National-Museum-Of-Fine-Arts-Orlando.d6154866.Vacation-Attraction)

- [Car rental Maitland ](https://www.expedia.ca/Car-Rentals-In-Maitland.d8442.Car-Rental-Guide)
- [Rental cars Orlando Intl. airport ](https://www.expedia.ca/Car-Rentals-In-Orlando-Intl.d5194573.Car-Rental-Guide)
- [Car rentals near Orlando ](https://www.expedia.ca/Car-Rentals-In-Orlando.d178294.Car-Rental-Guide)
- [Dollar Rent A Car Rental Cars in Maitland ](https://www.expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-Maitland.d8442-c43.Car-Rental-Guide-Suppliers)

- [Maitland Vacation Rentals ](https://www.expedia.ca/Maitland-Vacation-Rentals.d8442.Travel-Guide-VacationRentals)
- [Orlando Vacation Rentals ](https://www.expedia.ca/Orlando-Vacation-Rentals.d178294.Travel-Guide-VacationRentals)

- [Things to do in Orlando ](https://www.expedia.ca/Things-To-Do-In-Orlando.d178294.Travel-Guide-Activities)

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