Winter Park Vacations from US$259

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Your Winter Park Vacation

Say goodbye to planning worries and hello to a Winter Park vacation package. With the finer details organized before you take off, you can focus on discovering every inch of this city, starting with South Eola, which is great for shopping, markets and walking. Every trip to Winter Park needs a well-thought-out itinerary. Fill yours with big-name attractions like Amway Center, Camping World Stadium and Dr. Phillips Center for the Performing Arts. Expedia is here to help you escape the everyday. Tailor your vacation to Winter Park to suit your travel style, whatever that may be!

The Latest Winter Park Vacation Packages

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

Palazzo Lakeside Hotel

3 out of 5
per person
Jul 30 - Aug 5
found 1 day ago
Roundtrip flight included
Newark (EWR) to Orlando (MCO)
8/10 Very Good! (3,949 reviews)
Friendly staffs and clean property. The only thing i dont like is the shower is not too clean and water pressure isnt strong

Reviewed on 28 May 2024

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
per person
Jul 30 - Aug 5
found 1 day ago
Roundtrip flight included
Newark (EWR) to Orlando (MCO)
8.4/10 Very Good! (999 reviews)
Stayed in an upgraded suite building A. Clean and comfortable. Friendly professional staffs. Loved the washer/dryer, full kitchen with counter top/ seatings. 2 full bathrooms and 2 separated bedrooms was a plus for a family of 4.

Reviewed on 27 May 2024

Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
per person
Jul 17 - Jul 24
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
7.8/10 Good! (262 reviews)
It was all wonderful. Definitely will go back.

Reviewed on 29 Apr 2024

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
Jul 30 - Aug 5
found 1 day ago
Roundtrip flight included
Newark (EWR) to Orlando (MCO)
7.8/10 Good! (3,685 reviews)
We initially had some concerns though after speaking with someone, our concerns were resolved. Westgate is a beautiful resort and very clean. Most staff are friendly and accommodating. I would definitely stay there again.

Reviewed on 28 May 2024

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
per person
Jul 16 - Jul 22
found 1 day ago
Roundtrip flight included
Newark (EWR) to Orlando (MCO)
8.2/10 Very Good! (832 reviews)
We enjoyed our stay! The place was very clean, nice and convenient. The staff texted us everyday of our stay to be sure we didn't need anything which was very kind and helpful. We will definitely be back!

Reviewed on 28 May 2024

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 East Orlando Shopping Center and Harry P. Leu Gardens are two attractions nearby that you can check out.

Find hotel + flight trips in Baldwin Park

Winter Park Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Orlando Intl. Airport (MCO)
Population
29,900
Max Temp Winter
70ºF
Max Temp Summer
90ºF
Top Sights
Universal Orlando Resort, The Wizarding World of Harry Potter™ and Universal’s Islands of Adventure

Winter Park Hotel Deals

DoubleTree by Hilton Hotel Orlando at SeaWorld
DoubleTree by Hilton Hotel Orlando at SeaWorld
4 out of 5
10100 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
7/10 Good! (8,924 reviews)
Staff were great….amenities not so much
"Requested the Tower…was given a villa….even though Gold Hotels status and Hilton Honors member, then asked for a quiet room and was placed in a courtyard where people seemed to converge…nice feature was the front desk did reach out via text, but they did take their time responding…my husband did ..."

Reviewed on 27 May 2024

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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
8.2/10 Very Good! (6,312 reviews)
"Walked around and several good options for dining close by"

Reviewed on 28 May 2024

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DoubleTree by Hilton at the Entrance to Universal Orlando
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 $85 per night from May 29 to May 30
$85
$145 total
includes taxes & fees
29 May - 30 May
6.4/10 (5,461 reviews)
"Waterpark was great! Need more lounge chairs by the pools, though."

Reviewed on 28 May 2024

Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
See all 13,961 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

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Winter Park vacation package cost?
The most affordable Winter Park vacation package is US$259, 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 traveling style.
How do I get a cheap travel package to Winter Park?
Our Winter Park vacation 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 vacation 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 vacation?
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 vacation 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 vacation 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 vacation package?
Whether it’s your hotel or flight, you can cancel or alter it. Locked in your Winter Park vacation 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.

Discover the most popular places to visit in Winter Park

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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
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Universal Studios Florida

Thrill rides based on your favorite movies create this internationally acclaimed theme park.

Universal Studios Florida
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Universal Orlando Resort

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

Image for Aquatica Orlando

Aquatica Orlando

US$55
Per adult
82% of travellers recommend
Aquatica Orlando
Image for Orlando: Museum of Illusions Admission Ticket

Orlando: Museum of Illusions Admission Ticket

US$31
Per adult
84% of travellers recommend
Orlando: Museum of Illusions Admission Ticket
See all activities in Winter Park

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