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.
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Davis
Price was CA $958, price is now CA $555 per person
CA $555
per person
Nov 12 - Nov 19
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Orlando (MCO)
8.4/10 Very Good! (1,433 reviews)
I have been here multiple times it was a good experience! The staff was friendly.

Reviewed on Aug. 24, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $1,746, price is now CA $795 per person
CA $795
per person
Nov 2 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.8/10 Excellent! (1,013 reviews)
This was a good time!

Reviewed on Aug. 23, 2025

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was CA $1,365, price is now CA $698 per person
CA $698
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.4/10 Very Good! (1,001 reviews)
There was a very shady old looking red car parked outside our windows with loud music playing late into the night our last two nights

Reviewed on Aug. 19, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,168, price is now CA $618 per person
CA $618
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (5,177 reviews)
I didn't like the pools, the pictures i saw online wasn't what I actually saw in person. I was disappointed. There were no many entertainments at the facility

Reviewed on Aug. 25, 2025

ette hotel

ette hotel

5 out of 5
Price was CA $2,686, price is now CA $1,449 per person
CA $1,449
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9.8/10 Exceptional! (330 reviews)
Excellent service, food, location and staff! Thank you

Reviewed on Aug. 11, 2025

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

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

Ready to book your vacation to Winter Park?

 

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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 CA $128 per night from Sep 10 to Sep 11
CA $128
CA $144 total
Sep 10 - Sep 11
includes taxes & fees
8.2/10 Very Good! (6,574 reviews)
"N/A"

Reviewed on Aug. 25, 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 CA $121 per night from Sep 16 to Sep 17
CA $121
CA $136 total
Sep 16 - Sep 17
includes taxes & fees
8.8/10 Excellent! (2,934 reviews)
Loveeeee
"This is my favorite resort. My home away from home, I go at least 3 times a year. Highly recommend for coups or families!!"

Reviewed on Aug. 25, 2025

Marriott's Grande Vista
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Sep 3 to Sep 4
CA $197
CA $221 total
Sep 3 - Sep 4
includes taxes & fees
8.8/10 Excellent! (5,168 reviews)
"Only I add music on the main pool"

Reviewed on Aug. 25, 2025

Universal's Cabana Bay Beach Resort
See all 14,395 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
Family Vacations
Family Vacations

Discover the most popular places to visit in Winter Park

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(226 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(988 reviews)

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Studios Florida
Universal Studios Orlando which includes street scenes, a city and rides

Universal Orlando Resort

4.5/5(399 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

Aquatica Orlando

Aquatica Orlando

CA $74
per traveller
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $105
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Indoor Karting

Andretti Indoor Karting & Games in Orlando

CA $43
per adult
82% 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 $555 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.