Winter Park Vacations from $202

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Winter Park Vacation

When a getaway to the city is calling, answer it with a Winter Park vacation package. The neighborhood of Ivanhoe Village, which is great for dining, bars and pubs and shopping, makes a fantastic base for your adventures. Rollins College, Full Sail University and Altamonte Mall are just a few of the attractions worth exploring during your trip to Winter Park. Stop daydreaming and start adventuring. Check out the many options on Expedia today and put your Winter Park vacation plans in motion!

The Latest Winter Park vacation packages

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,277 reviews)
I love the size of the room very spacious and enough for me and my family

Reviewed on Jul 15, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Sep 29 - Oct 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
The hotel was just great! Is it just one of those apartment type of hotels which has a full kitchen. We stayed with a family of 4, so we had 2-bedroom apartment. Once you enter, there is a kitchen and a large living room, and 2 bedrooms on the left and right sides. It also has a washer and dryer, dish washer, stove, full size refrigerator and all kinds of kitchenware. The resort had all kinds of things to need to spend nice time. First, it is right next to a very nice lake. It has a very large pool, some basketball and other sport amities, table tennis, and some games for kids. It also has a large parking area, so parking is included. The location is very nice. It is right next to the International road where there are a lot of very cool restaurants. Also, it is very close to Disney parks, Universal, SeaWorld, and other attractions; all withing a short 5-10 minute drive.

Reviewed on Jul 15, 2025

ette hotel

ette hotel

5 out of 5
per person
Oct 4 - Oct 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.8/10 Exceptional! (313 reviews)
very friendly helpful staff. nice area with many restaurants and grocery stores around. clean rooms. elegant hotel

Reviewed on Jul 4, 2025

Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (354 reviews)
Nice place. Kids had a good time. Not encouraged to go there if you are a minority. You wont feel welcomed. The staff is great, but the type of people that go there arent really folks that likely share the same interests as you do. There are Confederate flags all over; etc. Hotel rooms are no bueno, old. IF you want something nice, you need to spend the money glamping or have your own trailer.

Reviewed on Jun 24, 2025

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
per person
Sep 29 - Oct 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
7.8/10 Good! (1,649 reviews)
It took a very long time for them to come see about why the microwave wasn’t working in the room along with the remote control

Reviewed on Jul 13, 2025

Don't see what you're looking for?
See all available trips from Columbus to Winter Park
View all trips

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
Default Image

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

Discover the most popular places to visit in Winter Park

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(2,427 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(9,273 reviews)

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

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

Universal Orlando Resort

4.5/5(4,155 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

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

$27
per adult
90% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
2014_AQ_KatasKookaburraCove_D4D_0772.jpg

Aquatica Orlando

$54
per traveler
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$85
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
See all activities in Winter Park

Winter Park Hotel Deals

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
$203 nightly
The price is $229 total per night from Jul 21 to Jul 22
$229 total
Jul 21 - Jul 22
Total includes taxes and fees
9.4/10 Exceptional! (3,383 reviews)
"Beautiful property, conveniently located I Terminal B. Excellent food."

Reviewed on Jul 15, 2025

Hyatt Regency Orlando International Airport
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
$84 nightly
The price is $95 total per night from Aug 4 to Aug 5
$95 total
Aug 4 - Aug 5
Total includes taxes and fees
8.2/10 Very Good! (6,474 reviews)
"Convenient for visiting Iniversal, large rooms with great beds, lovely large pool area, helpful staff, could have more and better restaurants or addition food options. Very useable transportation to Universal."

Reviewed on Jul 15, 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
$95 nightly
The price is $107 total per night from Aug 5 to Aug 6
$107 total
Aug 5 - Aug 6
Total includes taxes and fees
8.8/10 Excellent! (2,625 reviews)
"This hotel was excellent. It is close to all the attractions. Has a resort-like feel with many amenities during the day & night. The staff was also friendly. Hotel was clean. I would recommending staying here if you have a family or just coupling up, this place was great."

Reviewed on Jul 14, 2025

Marriott's Grande Vista
See all 14,759 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.

Find the Best Winter Park Vacation Packages

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

More vacations you might like

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?
You'll find cheap prices from $202 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?
If you'd like to book a cheap Winter Park vacation package, consider traveling in January, April and December. You're likely to find lower rates on hotels and airfares during these quieter months --- ideal for travelers wishing to save money.
How many days is enough for Winter Park?
Dedicate at least 2 days for your Winter Park vacation in order to discover all that makes this place special. Stroll around key areas, including Northeast Orlando and Downtown Orlando. Then make a beeline for top sights such as Winter Park History Museum and Hannibal Square Heritage Center. With a well-planned itinerary, you can keep busy with room for some rest and relaxation too. Want to travel beyond Winter Park? Consider fitting in a day trip or two.
Is it worth booking a vacation package to Winter Park?
Popular for its golfing, shopping and markets, a Winter Park vacation has something for everyone. Be sure to check out key sights like Winter Park Village and Casa Feliz Historic Home Museum, and consider renting a set of wheels for day trips to explore even more.
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 the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Winter Park.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and meals to experiences and flights. Your hotel will likely be the biggest expense during your trip to Winter Park.
  3. Organize your Winter Park escape with Expedia's trip planning tool: Look for and book hotels and activities all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Winter Park together.
  4. 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.
  5. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Winter Park vacation package that brings all your bookings together.
  6. Book experiences or activities in advance: Whether it's a ticket to a big attraction or a walking tour, you won't have to worry about missing out on Winter Park's best offerings. Find all the exciting things to do in Winter Park with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Winter Park vacation packages?
Secure your ideal getaway to Winter Park with help from Expedia's Book Now, Pay Later vacations. No need to save up or wait until payday --- we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snap up cheap deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.