Winter Park Vacations from ₩340,774

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Winter Park Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Happy Travelers RV Resort

Happy Travelers RV Resort

3 out of 5
per person
Oct 27 - Oct 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Orlando (ORL)
9.4/10 Exceptional! (221 reviews)
Cabin is cute. Gives you a camping vibe with a hotel feel. Only disappointment during our 3 days stay was the pool was closed! Not acceptable during the peak of summer.

Reviewed on Aug 6, 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
Default Image

Baldwin Park

5/5(1 area review)

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

Find the Best Winter Park Vacation Packages

Winter Park Hotel Deals

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 ₩135,943 per night from Aug 20 to Aug 21
₩135,943
₩152,935 total
Aug 20 - Aug 21
includes taxes & fees
8.2/10 Very Good! (6,521 reviews)
"Great"

Reviewed on Aug 5, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is ₩106,413 per night from Aug 20 to Aug 21
₩106,413
₩119,716 total
Aug 20 - Aug 21
includes taxes & fees
8.4/10 Very Good! (4,719 reviews)
"The room was clean, water nice and hot, plenty of eateries to choose from, beds was comfortable as hell. Would I come back? Hell yeah!! I really enjoyed my weekend here. Hotel staff was A1!! Fantabulous customer service!! No complaints here."

Reviewed on Aug 4, 2025

Rosen Inn at Pointe Orlando
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is ₩221,722 per night from Aug 12 to Aug 13
₩221,722
₩249,437 total
Aug 12 - Aug 13
includes taxes & fees
8.8/10 Excellent! (5,122 reviews)
"Good !!!"

Reviewed on Aug 5, 2025

Universal's Cabana Bay Beach Resort
See all 13,938 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.

Discover the most popular places to visit in Winter Park

Walt Disney World® Resort

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.

Walt Disney World® Resort
Universal Studios Florida™

Universal Studios Florida

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

Universal Studios Florida
Universal Studios Orlando showing street scenes, a city and rides

Universal Orlando Resort

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

Universal Orlando Resort

Frequently asked questions

How much does a Winter Park vacation package cost?
You'll find cheap prices from ₩340,774 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.