Winter Park Vacation Packages
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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!
Top Winter Park Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort
CA $524
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.2/10 Very good! (2,052 reviews)
The place was very clean organized but when I reserved the room was with 2 full size bed with a kitchen, they give me one king size bed and a sofa bed that no one can sleep on it as soon as you lay down you go almost to the floor and if you try to move was making a lot of noise, beside that when i make my reservation with expidia i made all payments in full but when I reached there they charge me $272 for the resort fee im very disappointed
Reviewed on Aug 26, 2026
Westgate Blue Tree Resort in Lake Buena Vista
CA $590
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,001 reviews)
Nice property overall. I love the fact that you have balconies, and individual washer and dryers in the unit. However, I do not like how you say there's a $50 deposit but you charge $100?
Reviewed on Aug 25, 2026
Westgate Palace Hotel / Universal / I-Drive
International Drive District
CA $904
per person
Oct 9 - Oct 13
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9/10 Wonderful! (1,308 reviews)
Staff was very friendly and informative. Location was great. I will be staying here again.
Reviewed on Aug 25, 2026
Ready to book your vacation to Winter Park?
Winter Park Hotel Deals
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
Fully refundable
CA $98
CA $110 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (6,974 reviews)
"The hotel was disgusting!!!! The rooms were outdated, the carpets stank, and all the staff could offer was for us to switch. We switched rooms 3 times over three days and each room was dirty. The first was 215–the linens wetr dirty, next was 217–which smelled like a mixture of mildew and tea tree ..."
Reviewed on Aug 28, 2026
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
CA $171
CA $192 total
Sep 22 - Sep 23
includes taxes & fees
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
Fully refundableReserve now, pay when you stay
CA $205
CA $230 total
Aug 30 - Aug 31
includes taxes & fees
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.
Stay near popular Winter Park attractions
Photo by Jay Mullenix
Full Sail University
8.4/10 (73 reviews)
Enjoy the collegiate vibe when you visit Full Sail University, during your trip to Winter Park. Discover the area's top-notch restaurants and its great live music.
Morse Museum of American Art
9.8/10 (68 reviews)
If you admire Tiffany lamps and chandeliers, visit this museum to see the most comprehensive collection of works by the designer behind them.
Casa Feliz Historic Home Museum
9.2/10 (34 reviews)
This house serves as the backbone for preserving other historic buildings in the city. Visit this beautiful building for its cultural events.
Winter Park History Museum
7.2/10 (5 reviews)
Find out about how this community began as the result of a doctor’s advice. Go on a walking tour to learn other interesting facts.
Kraft Azalea Gardens
9.6/10 (24 reviews)
Love is in the air practically everywhere you go in this park. Spend serene time under the trees near a lake where birds offer entertainment.
Mead Garden
8.4/10 (27 reviews)
Explore the great outdoors at Mead Garden, a lovely green space in Winter Park. Stroll along the area's lakeside, or simply savor its top-notch restaurants.
Winter Park Village
9.6/10 (323 reviews)
During your trip to Winter Park, you can enjoy retail therapy at Winter Park Village. Stroll along the area's lakeside, or simply savor its top-notch restaurants.
Lee Road Shopping Center
9.0/10 (38 reviews)
During your visit to Winter Park, you can search for that perfect souvenir at Lee Road Shopping Center. Wander the lakeside and picturesque gardens in the area.
What to do in Winter Park
Universal Orlando Resort Theme Park Tickets (US & Canada)
CA $229
per adult
86% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
CA $38
per adult
92% of travellers recommend
WonderWorks All Access After Dark
CA $38
per traveller
88% of travellers recommend
Frequently asked questions
How much does a Winter Park vacation package cost?
You can pick up a vacation package to this destination from CA $524 on Expedia. But how much your vacation to Winter Park costs will depend on the season, length of stay and hotel choice.
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. Opting to travel in quieter periods means you can usually find lower prices on accommodations and flights.
How many days is enough for Winter Park?
Allow at least 2 days for your Winter Park vacation if you're hoping to immerse yourself in everything that makes this destination special. Stroll around popular areas, including Northeast Orlando and Ivanhoe Village. Then check out top attractions such as Tinker Field and Dr. Phillips Centre for the Performing Arts. With a well-planned itinerary, you'll be kept busy with room for some relaxation too. Want to go beyond Winter Park? Consider an excursion or two.
Is it worth booking a vacation package to Winter Park?
Winter Park has all the ingredients you need for a fantastic getaway — golfing, shopping and markets are just the start. Whether you want to visit sights like Casa Feliz Historic Home Museum and Albin Polasek Museum and Sculpture Gardens, or take the path less travelled, you'll find plenty to experience on your Winter Park vacation.
How to find the best Winter Park package deals?
Bagging a cheap Winter Park package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Winter Park package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Winter Park vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Winter Park vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Winter Park?
If you're planning a spontaneous Winter Park trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Winter Park?
- Choose when to get away: Check your schedule and get your bags packed. Your favourite season and the activities available will also help you decide when to escape to Winter Park.
- Set your budget: Consider expenses like flights, food and transportation when calculating how much to save for your trip to Winter Park. Then, select a property that suits your budget, whether that's a wallet-friendly option or a more upscale getaway.
- Decide how many days away: Start by making a list of all the sights and activities you'd like to get to in Winter Park. Then, estimate how long you'll need at each, including any travel time.
- Combine your accommodations and airfare: After you've settled on your dates and duration, lock in the ideal Winter Park vacation package for you.
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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.
