Winter Park Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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    Save up to ฿4,531 when you book a flight and hotel together*
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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

If you're looking for some top things to see and do in Baldwin Park and surrounding area, you can visit Orlando Fashion Square and East Orlando Shopping Center.

Find hotels in Baldwin Park

Top hotels in Winter Park

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4 out of 5
8800 Vistana Centre Dr, Orlando, FL
The price is ฿3,822 per night from 16 Jul to 17 Jul
฿3,822
฿4,300 total
16 Jul - 17 Jul
includes taxes & fees
9.2/10 Wonderful! (3,103 reviews)
"The room was beautiful and clean. The staff were great and so helpful. They had so many things to do and the hotel was close to so many things to eat and do. Most definitely staying again!"

Reviewed on 22 Jun 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Marriott's Grande Vista
Marriott's Grande Vista
4 out of 5
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is ฿3,377 per night from 14 Jul to 15 Jul
฿3,377
฿3,799 total
14 Jul - 15 Jul
includes taxes & fees
8.8/10 Excellent! (2,530 reviews)
"The room and areas around were clean and safe"

Reviewed on 21 Jun 2025

Marriott's Grande Vista
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 ฿5,301 per night from 25 Jun to 26 Jun
฿5,301
฿5,964 total
25 Jun - 26 Jun
includes taxes & fees
8.4/10 Very Good! (4,529 reviews)
"It is within walking distance of the Convention center on International Drive. Check in was quick and price was reasonable. The room was comfortable and made up. The hotel has several buildings. The building itself looks like it needs a facelift. There is a CVS nearby and restaurants."

Reviewed on 22 Jun 2025

Rosen Inn at Pointe Orlando
See all 14,462 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.

Frequently asked questions

How much does a Winter Park holiday package cost?
You'll find cheap prices 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 holiday 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 holiday packages. Travelling in less busy periods means you can typically find reduced prices on accommodation and flights.
How many days is enough for Winter Park?
Winter Park holidays 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 Centre 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 holiday 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 holiday, 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 holiday 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 holiday package as soon as possible.
Is it cheaper to book a Winter Park holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can personalise 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 holiday 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 holiday in Winter Park.
  2. Plan your budget wisely: Besides the cost of your accommodation, 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 holiday package that brings all your bookings together.

Popular places to visit

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(63 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(273 reviews)

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

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

Universal Orlando Resort

4.5/5(166 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

฿2,470
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
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Aquatica Orlando

฿1,678
per traveller
82% of travellers recommend
Aquatica Orlando
Explore the Wonderful World of the Oz Books in a way that you have never seen before...

Wizard of OZ Museum tour

฿972
per adult
100% of travellers recommend
Wizard of OZ Museum tour
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.