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

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,398, price is now CA $841 per person
CA $841
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very good! (2,105 reviews)
The property is very nice but wish the staff are more helpful.

Reviewed on Nov 1, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $2,414, price is now CA $1,424 per person
CA $1,424
per person
Dec 18 - Dec 23
found 14 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)

Ocean Landings Resort and Racquet

Ocean Landings Resort and Racquet

2.5 out of 5
Price was CA $2,274, price is now CA $1,384 per person
CA $1,384
per person
Jan 11 - Jan 18
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Orlando (MCO)
7.2/10 Good! (50 reviews)
This is an older property but very clean and well maintained. The two ocean front buildings are under a major renovation but there is still access to the beach. We would stay again.

Reviewed on Oct 30, 2026

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was CA $1,635, price is now CA $1,024 per person
CA $1,024
per person
Jan 6 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9/10 Wonderful! (4,064 reviews)
The owner Peter, and staff, were so friendly and helpful. Felt like we have known them for years. The breakfast room was under renovation and will be so welcoming when completed. They are steadily working on it to make it that more inviting. As it is now, I had no complaints. Happy Stay!!!!! Highly recommend!!!!price was also very reasonable. Diane and Dennis. From West Virginia!!!!

Reviewed on Nov 2, 2026

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was CA $2,111, price is now CA $1,345 per person
CA $1,345
per person
Jan 6 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9.6/10 Exceptional! (1,234 reviews)
**5 Stars! Our New Favorite Hotel! ⭐⭐⭐⭐⭐** We absolutely loved our stay at The Delaney Hotel! The hotel was exceptionally clean, and the staff was wonderful. Everyone was friendly, welcoming, and made us feel right at home. It's always refreshing to stay somewhere that truly values cleanliness and great customer service. The Delaney has officially become our hotel of choice whenever we visit Orlando. We look forward to staying here again!

Reviewed on Nov 1, 2026

Ready to book your vacation to Winter Park?

 

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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
The price is CA $306 per night from Nov 23 to Nov 24
CA $306
CA $344 total
Nov 23 - Nov 24
includes taxes & fees
Hyatt Regency Orlando International Airport
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 CA $155 per night from Nov 30 to Dec 1
CA $155
CA $175 total
Nov 30 - Dec 1
includes taxes & fees
Sheraton Vistana Resort Villas, Lake Buena Vista/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 CA $134 per night from Nov 28 to Nov 29
CA $134
CA $151 total
Nov 28 - Nov 29
includes taxes & fees
9/10 Wonderful! (5,343 reviews)
"Hot tub and sauna were awesome"

Reviewed on Nov 2, 2026

Marriott's Grande Vista
See all 16,787 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
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Stay near popular Winter Park attractions

A bar with wooden decor, a TV screen, and a bartender wearing a red jersey.
Photo by Jay Mullenix
Open 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 acclaimed theater scene.
See properties

What to do in Winter Park

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets (US & Canada)

CA $222
per adult
86% of travellers recommend
Universal Orlando Resort Theme Park Tickets (US & Canada)
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

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

CA $39
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Multi Level Tracks

Andretti Indoor Karting & Games in Orlando

CA $44
per adult
88% of travellers recommend
Andretti Indoor Karting & Games in Orlando
See all activities in Winter Park

Frequently asked questions

How much does a Winter Park vacation package cost?
You can pick up a vacation package to this destination from CA $841 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.