Winter Park Vacations

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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

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 SAR 347 per night from Jun 15 to Jun 16
SAR 347
SAR 391 total
15 Jun - 16 Jun
includes taxes & fees
8.2/10 Very Good! (6,277 reviews)
"The staff was amazing. The only issue was checking in. We stood online for one hour because there was an event going on"

Reviewed on 5 June 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 SAR 387 per night from Jul 6 to Jul 7
SAR 387
SAR 435 total
6 Jul - 7 Jul
includes taxes & fees
8.8/10 Excellent! (2,475 reviews)
"This place gets five stars. Everyone there was polite and friendly. The area was very clean and well kept. The room was nice and comfortable felt like you were at home."

Reviewed on 4 June 2025

Marriott's Grande Vista
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
Fully refundableReserve now, pay when you stay
The price is SAR 285 per night from Jul 6 to Jul 7
SAR 285
SAR 321 total
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (2,997 reviews)
"Our second visit to Vistana and discovered even more of the resort. The kids loved the slide pool and the activities run around the Fountains pool. We enjoyed playing pickleball. The onsite shop is pricey but only a short uber to Walmart to stock up on essentials."

Reviewed on 5 June 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
See all 14,339 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 vacation 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 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 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.

Discover the most popular places to visit in Winter Park

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(2,427 reviews)

Have a fun-filled day 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 acclaimed theater scene in this walkable area.

Walt Disney World® Resort
Universal Studios Florida™

Universal Studios Florida

4.5/5(9,273 reviews)

Enjoy the excitement at Universal Studios Florida and find out why this is a popular theme park in Orlando. Experience the acclaimed theater scene and entertainment choices in this family-friendly area.

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

Universal Orlando Resort

4.5/5(4,155 reviews)

Have a fun-filled day at Universal Orlando Resort and see why people love this theme park in Orlando. Check out the shops and top-notch restaurants in this family-friendly area.

Universal Orlando Resort