Winter Park Vacation Packages

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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, Full Sail University and Altamonte Mall 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.
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
per person
May 23 - May 26
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very Good! (1,011 reviews)
Great space. Full kitchen.

Reviewed on Mar. 26, 2025

Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Davis
Save 100% on your flight
per person
May 2 - May 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very Good! (1,276 reviews)
Everything was great. Staff was very friendly and accommodating.

Reviewed on Mar. 25, 2025

Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
Save 100% on your flight
per person
Jun. 15 - Jun. 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,230 reviews)
Friendly staff. Everyone was super cool. Beautiful property. Large rooms. I’d go back.

Reviewed on Mar. 23, 2025

Margaritaville Cottages Orlando by VStays

Margaritaville Cottages Orlando by VStays

4 out of 5
Save 100% on your flight
per person
Jun. 15 - Jun. 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9/10 Wonderful! (1,000 reviews)
We really enjoyed having the pool attached to the house

Reviewed on Mar. 22, 2025

Century Millenia

Century Millenia

3 out of 5
Florida Center
Save 100% on your flight
per person
Jun. 15 - Jun. 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.8/10 Excellent! (48 reviews)
Great property for our Disney trip

Reviewed on Mar. 24, 2025

Where to stay in Winter Park

Find the best Winter Park areas and neighborhoods for the activities you enjoy most. Learn more about Winter Park
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Baldwin Park

Baldwin Park might not have many top sights, but Orlando Fashion Square and East Orlando Shopping Center are two attractions nearby that you can check out.

Find hotels in Baldwin Park

Ready to book your vacation to Winter Park?

 

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Winter Park Hotel Deals

Holiday Inn Resort Orlando Suites - Waterpark by IHG
Holiday Inn Resort Orlando Suites - Waterpark by IHG
3.5 out of 5
14500 Continental Gateway, Orlando, FL
Fully refundable
The price is CA $114 per night from Apr. 2 to Apr. 3
CA $114
CA $198 total
includes taxes & fees
Apr 2 - Apr 3
7/10 Good! (2,390 reviews)
"Room was clean with plenty of space. We didn’t get a chance to use the water park area, but what we saw of it looked very nice"

Reviewed on Mar. 24, 2025

Holiday Inn Resort Orlando Suites - Waterpark by IHG
DoubleTree by Hilton Hotel Orlando at SeaWorld
DoubleTree by Hilton Hotel Orlando at SeaWorld
4 out of 5
10100 International Drive, Orlando, FL
The price is CA $133 per night from Apr. 20 to Apr. 21
CA $133
CA $185 total
includes taxes & fees
Apr 20 - Apr 21
7.2/10 Good! (5,801 reviews)
"The outdoor pools and bar were great for our family. Everything was very clean and neat. The rooms in the tower were comfortable and had everything we needed, but are dated and in need of some TLC."

Reviewed on Mar. 24, 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
DoubleTree by Hilton at the Entrance to Universal Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando
4 out of 5
5780 Major Blvd, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Apr. 2 to Apr. 3
CA $157
CA $176 total
includes taxes & fees
Apr 2 - Apr 3
8.2/10 Very Good! (6,302 reviews)
"Great location!!"

Reviewed on Mar. 25, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
See all 14,090 properties in Winter Park
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Winter Park vacation package cost?
You’ll find cheap prices from CA $589 on Expedia for your Winter Park getaway. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Winter Park costs.
What are the cheapest months to go to Winter Park?
January, February and July are great times to look for cheap Winter Park vacation packages. Traveling in less busy periods means you can typically find reduced prices on accommodations and flights.
How many days is enough for Winter Park?
Winter Park vacations come in all shapes and sizes, but to get a real feel for this destination, we think 2 days is about right. In this timeframe, you can fit in top attractions like Winter Park History Museum and Hannibal Square Heritage Center as well as underrated gems. Don’t forget to visit cool areas such as Northeast Orlando and Ivanhoe Village either. If you’re clever with your time, you can even allow for a day trip from Winter Park too.
Is it worth booking a vacation package to Winter Park?
Whether you want to visit major attractions such as Casa Feliz Historic Home Museum and Albin Polasek Museum and Sculpture Gardens on your Winter Park vacation, or coming for its excellent golfing, shopping and markets, there’s something for everyone here. With so much to do, you’ll soon learn why so many people think Winter Park is a good vacation destination.
How to find the best Winter Park package deals?
Use Expedia’s filter tool to help you find some terrific Winter Park package deals. When you begin your search, just set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your escape for midweek, or browse for Winter Park package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it’s usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Winter Park vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can personalize your Winter Park escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Winter Park?
If you have your Winter Park travel dates finalized, book as early as you can to snap up some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Winter Park?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the available activities will also help you decide when to vacation in Winter Park.
  2. Plan your budget wisely: Besides the cost of your accommodations, you should consider other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that may arise during your trip to Winter Park.
  3. Work out your trip length: Consider how much time you’d like to spend discovering Winter Park. Plan your days so you can get to all the activities and attractions you’re interested in at a comfortable pace.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that’s left now is to find a Winter Park vacation package that brings all your bookings together.

Discover the most popular places to visit in Winter Park

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(226 reviews)

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.

Walt Disney World® Resort
Universal Studios Florida

Universal Studios Florida

4.5/5(988 reviews)

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

Universal Studios Florida
Universal Studios Orlando which includes street scenes, a city and rides

Universal Orlando Resort

4.5/5(399 reviews)

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

Universal Orlando Resort

What to do in Winter Park

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $110
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
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Aquatica Orlando

CA $71
per traveller
82% of travellers recommend
Aquatica Orlando
WonderWorks All Access After Dark

WonderWorks All Access After Dark

CA $40
per traveller
86% of travellers recommend
WonderWorks All Access After Dark
See all activities in Winter Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.