Winter Park Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 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

Top hotels in Winter Park

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 S$122 per night from 18 Dec to 19 Dec
S$122
includes taxes & fees
18 Dec - 19 Dec
8.2/10 Very Good! (6,360 reviews)
"Be aware of the $35 a day parking fee."

Reviewed on 30 Nov,2024

DoubleTree by Hilton at the Entrance to Universal Orlando
Hyatt Regency Orlando International Airport
Hyatt Regency Orlando International Airport
4 out of 5
9300 Jeff Fuqua Boulevard, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is S$307 per night from 16 Dec to 17 Dec
S$307
includes taxes & fees
16 Dec - 17 Dec
9.2/10 Wonderful! (3,106 reviews)
"Check-in was easy and staff was very friendly."

Reviewed on 1 Dec,2024

Hyatt Regency Orlando International Airport
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
3.5 out of 5
14500 Continental Gateway, Orlando, FL
Fully refundable
The price is S$187 per night from 5 Dec to 6 Dec
S$187
includes taxes & fees
5 Dec - 6 Dec
7/10 Good! (1,534 reviews)
Best Family Experience Ever!!!
"This hotel was the best part of our trip!! We didn't want to leave the hotel. I mean, the water park was spectacular, the restaurants onsite make it super easy when traveling with little ones. The room was very spacious and clean. It offers everything you need to have a pleasant family trip. we are ..."

Reviewed on 2 Dec,2024

Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
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?
The most affordable Winter Park holiday package is , so the trip of your dreams can become a reality — without burning a hole in your pocket. Bundle flights, hotels, car rentals and more to tailor a package that matches your travelling style.
How do I get a cheap travel package to Winter Park?
Our Winter Park holiday packages promise plenty of savings for the savvy explorer. For the best deals, simply bundle your hotel, flights and extras (such as activities) into a neat and tidy package. But impressive bargains are only the start of your next unforgettable adventure. Book with Expedia and you’ll have more than 550 airlines and 1,000,000 hotels across the globe to pick from. Whatever your budget, there’s a holiday package here just for you.
Where should I stay in Winter Park?
With loads to explore in Winter Park, it’s a good idea to book a hotel near its attractions. Full Sail University, Rollins College and Casa Feliz Historic Home Museum are some interesting ones to put on your itinerary.
What are the top hotels in Winter Park?
The Alfond Inn will make a great base for your Winter Park getaway. Located in Goldenrod, it’s one of the area’s leading hotels.
How far in advance should I book my Winter Park holiday?
Earlier is always better. Airlines usually advertise flight tickets nearly 12 months ahead of departure, and this is an excellent opportunity to pick up some of the cheapest prices. Just been told you need to take some holiday time in a few weeks? That’s alright! Expedia are never short of fantastic deals to send you on the getaway of your dreams, at an affordable price.
What does an Expedia Winter Park travel package include?
Expedia has everything you need to plan your Winter Park getaway, but how your package is structured is totally up to you. Pick from any combination of hotels, flights and rental cars. Searching for some tours or activities to keep you busy? Once you’ve made your booking, you can add them too. No matter your style or budget, there’s a deal to suit your needs.
What should I know before booking a Winter Park travel package?
We already have low prices. However, you’ll enjoy an even better deal when you book your hotels, flights and car rentals together. With an Expedia package, you’ll always get transparent pricing and tons of choice.
Can I choose my airline with a Winter Park Expedia holiday package?
Definitely. Expedia has more than 550 partner airlines to select from around the world. With so much choice, finding the perfect carrier to whisk you away to Winter Park will be a breeze.
If I'm not able to travel, can I cancel my Winter Park holiday package?
Whether it’s your hotel or flight, you can cancel or alter it. Locked in your Winter Park holiday package in the last 24 hours? You may be able to make any changes for free. For bookings made more than 24 hours ago, you may incur a charge from your hotel, airline or car rental company. For more information, visit our Customer Service Portal. We’ll help you each step of the way.

Popular places to visit

What to do in Winter Park

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.