Winter Park Holidays

Book a Hotel + Flight or Car together to unlock savings

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

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 2.435.940 ₫ per night from 10 Sept to 11 Sept
2.435.940 ₫
2.740.433 ₫ total
10 Sept - 11 Sept
includes taxes & fees
8.4/10 Very Good! (6,537 reviews)
"The hotel is beautiful. Staff are amazing. The hotel was very clean which my family and I really enjoyed. It was a walk away from Universal Studios which was really great. You definitely got your steps in walking there and back."

Reviewed on 17 Aug 2025

DoubleTree by Hilton at the Entrance to Universal 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 2.290.918 ₫ per night from 7 Sept to 8 Sept
2.290.918 ₫
2.577.284 ₫ total
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (2,877 reviews)
"Beautiful property. Staff were polite and very helpful. Internet worked great. Parking on property was perfect. Access to pools was great."

Reviewed on 17 Aug 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 2.143.532 ₫ per night from 25 Aug to 26 Aug
2.143.532 ₫
2.411.769 ₫ total
25 Aug - 26 Aug
includes taxes & fees
8.4/10 Very Good! (4,796 reviews)
"Older property with outdated amenities, but clean and affordable."

Reviewed on 14 Aug 2025

Rosen Inn at Pointe Orlando
See all 14,589 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.

Popular places to visit

Walt Disney World® Resort

Walt Disney World® Resort

Enjoy the rides and games at Walt Disney World® Resort and find out why this is a popular theme park in Lake Buena Vista. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Walt Disney World® Resort
Universal Studios Florida® showing rides, a city and street scenes

Universal Orlando Resort

Enjoy the excitement at Universal Orlando Resort and find out why this is a popular theme park in Orlando. Visit the shops and top-notch restaurants in this family-friendly area.

Universal Orlando Resort
Disney Springs™

Disney Springs™

You can find the perfect gifts to bring home when you visit Disney Springs™, a favourite shopping spot in Lake Buena Vista. Experience the entertainment choices and acclaimed theatre scene in this family-friendly area.

Disney Springs™

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.