How much does a Winter Park vacation package cost?

You'll find cheap prices from $317 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?

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. 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. 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. 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. 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. 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.

Winter Park Vacation Packages 2026 from $317

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.

Palazzo Lakeside Hotel

$317

per person

Mar 16 - Mar 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8.2/10 Very Good! (5,145 reviews)

Staff was friendly, hotel was clean and rooms look nice……But walls are paper thin and you can hear everything going on outside and inside. And we had no hot water in the shower. But very safe location.

Reviewed on Jan 10, 2026

Westgate Town Center Resort

Save 100% on your flight

$356

per person

Mar 16 - Mar 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8/10 Very Good! (1,367 reviews)

We stayed in Building 5100, Room A, and had a mixed experience. Pros: The room was spacious and comfortable with a full kitchen, dining table, separate living area, bedroom, and a bathroom with a hot tub. The location was excellent, close to the Disney parks, with plenty of parking and low noise levels. The pool near our building was clean with great hours. The main resort pool with the lazy river and slides was fun, and Javier the security guard was attentive, polite, and friendly. The Mexican restaurant on site had good food, drinks, and service. Check in and check out were easy. Cons: Cleanliness and service were disappointing. Upon arrival, we found a clipped fingernail in our bed. We called room service at 4:00 pm, but no one arrived until nearly 10:00 pm after multiple calls. We also requested room cleaning for the next day, which was approved, but the room was never cleaned. Water pressure in the bathroom was very poor. Paying extra to access the main resort pool felt unreasonable, especially since it closed for cleaning for almost an hour and a half, leaving limited time before closing. Bar drinks were good, but lines were long due to only two bartenders, and the second floor bar never opened, forcing guests downstairs. Overall, the room and location were strong, but service issues and extra fees negatively impacted our stay.

Reviewed on Jan 10, 2026

Westgate Cocoa Beach Resort

$1,061

per person

Feb 22 - Feb 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8.8/10 Excellent! (500 reviews)

Everything was great! Staff were super!!

Reviewed on Dec 22, 2025

Westgate Palace Hotel / Universal / I-Drive

International Drive District

$549

per person

Mar 16 - Mar 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8.8/10 Excellent! (1,085 reviews)

The room had not been serviced for two weeks, and the parking facilities were unsatisfactory; otherwise, the stay was acceptable.

Reviewed on Jan 11, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$439

per person

Mar 16 - Mar 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8.2/10 Very Good! (5,482 reviews)

Only thing was if they call and offer cookies and breakfast, its so they can try and get you to do a timeshare presentation. Clean, nice pools but waterpark costs $$. Nice sunset views.

Reviewed on Jan 11, 2026

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Winter Park Hotel Deals

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL

Fully refundableReserve now, pay when you stay

$133 nightly

$150 total

Jan 13 - Jan 14

Total with taxes and fees

8.8/10 Excellent! (5,996 reviews)

The mobile check-in counter representative was amazing. Everything about this hotel is remarkable…

Reviewed on Jan 10, 2026

Wyndham I-Drive Avanti Resort & Conference Center

6515 International Drive Orlando FL

Fully refundableReserve now, pay when you stay

$80 nightly

$90 total

Jan 14 - Jan 15

Total with taxes and fees

7.2/10 Good! (4,065 reviews)

everything

Reviewed on Jan 6, 2026

Rosen Inn at Pointe Orlando

9000 International Drive Orlando FL

Fully refundableReserve now, pay when you stay

$74 nightly

$84 total

Feb 8 - Feb 9

Total with taxes and fees

8.4/10 Very Good! (5,559 reviews)

Very good hotel, easy on your pocket, kept very well and has lots of places around it to enjoy your stay.

Reviewed on Jan 7, 2026

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.

Things to do in and around Winter Park

Winter Park, Florida, offers a delightful mix of family-friendly activities and entertainment. Enjoy a memorable ski vacation at the resort, featuring chairlift rides and thrilling adventures at the nearby adventure park. Explore the charming shopping areas and immerse yourself in the local culture, making it a perfect destination for all ages seeking fun and excitement.

Shopping

Winter Park Village offers a vibrant shopping experience with entertainment and unique shops. If you're up for a drive, check out Altamonte Mall, just 5 miles away, featuring a variety of stores and family-friendly options. Don't miss All Fired Up for personalized gifts and souvenirs.

Recreation

Experience the energetic atmosphere at the Kia Center, just 5 miles away, perfect for sports enthusiasts. Enjoy a romantic night or family fun at The Plaza Theatre, located 4 miles from Winter Park. Don't miss live music at The Social, also 5 miles away, offering vibrant entertainment.

Adventure

Experience the thrill at Boardwalk Bowl Entertainment Center, where you can enjoy arcade games and family fun, located 7 miles from Winter Park. For more excitement, head to Lil 500 Go-Karts, just 3 miles away, for exhilarating kart racing. Don’t miss the action at Paintball World Sports Complex, also 7 miles away.

Nightlife

In Winter Park, Florida, enjoy a vibrant nightlife with trendy bars and cozy lounges along Park Avenue. Check out the live music scene at local venues and savor craft cocktails at rooftop bars, all while soaking in the charming ambiance of this picturesque town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Winter Park

Winter Park, Florida, is perfect for family-friendly and entertainment-themed vacations, offering a range of attractions such as urban parks, beautiful lakes, and art museums. Visitors can enjoy outdoor activities and cultural experiences at various points of interest. Be sure to explore options near the Winter Park Visitor Center for additional recommendations and things to do during your stay.

Orlando Science Center: Located 3 miles from Winter Park, this interactive science museum offers engaging exhibits and hands-on activities perfect for families. Experience the wonders of science through live demonstrations and planetarium shows that inspire curiosity and learning.
Rollins College: Situated in the heart of Winter Park, this modern university boasts stunning architecture and beautiful lakeside views. Explore the picturesque campus, rich in history and vibrant city vibes, while enjoying cultural events and art exhibitions throughout the year.
Full Sail University: Also located within Winter Park, this historic university is known for its innovative programs in entertainment, media, and arts. Immerse yourself in a creative atmosphere that celebrates culture and fosters artistic expression among students and faculty.

Best time to go to Winter Park

The best time to visit Winter Park is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with moderate rain. January is its coolest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	60.3°F (15.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
February	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
March	67.5°F (19.7°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
April	72.5°F (22.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
May	77.0°F (25.0°C)	Light Rain	Mostly Sunny	Slightly Low	Average
June	81.0°F (27.2°C)	Light Rain	Mostly Sunny	Average	Average
July	82.4°F (28.0°C)	Light Rain	Mostly Sunny	Average	Average
August	82.6°F (28.1°C)	Moderate Rain	Mostly Sunny	Slightly Low	Slightly Low
September	80.2°F (26.8°C)	Light Rain	Mostly Sunny	Average	Slightly Low
October	75.0°F (23.9°C)	Light Rain	Mostly Sunny	Average	Average
November	68.2°F (20.1°C)	No Rain	Mostly Sunny	Slightly Low	Slightly Low
December	64.0°F (17.8°C)	No Rain	Mostly Sunny	Average	Slightly High

Tips to save on your trip to Winter Park

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling during the off-peak season (typically August to September and November) for more affordable package holidays to Winter Park.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

Language

English

Currency

U.S dollars

Closest Airport

Orlando Intl. Airport (MCO)

Population

29,900

Max Temp Winter

70ºF

Max Temp Summer

90ºF