How much does a Winter Park holiday package cost?

You'll find cheap prices from €896 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 holiday to Winter Park costs.

What are the cheapest months to go to Winter Park?

January, February and July are great times to look for cheap Winter Park holiday packages. Travelling in less busy periods means you can typically find reduced prices on accommodation and flights.

How many days is enough for Winter Park?

Winter Park holidays come in all shapes and sizes, but to get a real feel for this destination, we think 2 days is about right. In this timeframe, you can fit in top attractions like Winter Park History Museum and Hannibal Square Heritage Centre as well as underrated gems. Don't forget to visit cool areas such as Northeast Orlando and Ivanhoe Village either. If you're clever with your time, you can even allow for a day trip from Winter Park too.

Is it worth booking a holiday package to Winter Park?

Whether you want to visit major attractions such as Casa Feliz Historic Home Museum and Albin Polasek Museum and Sculpture Gardens on your Winter Park holiday, or coming for its excellent golfing, shopping and markets, there's something for everyone here. With so much to do, you'll soon learn why so many people think Winter Park is a good holiday destination.

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 holiday package as soon as possible.

Is it cheaper to book a Winter Park holiday as a package?

An Expedia holiday package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can personalise 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 holiday 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 when to travel: Check your calendar and get your bags packed. Your preferred season and the available activities will also help you decide when to holiday in Winter Park. Plan your budget wisely: Besides the cost of your accommodation, you should consider other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that may arise during your trip to Winter Park. 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 flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Winter Park holiday package that brings all your bookings together.

Winter Park 2026 Holidays & City Breaks | Flight + Hotel

Top Flight + Hotel Deals in Winter Park

Price found within the past 48 hours. Click for updated prices.

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

€896

per person

7 Sept - 11 Sept

found 24 hours ago

Return direct flight included

Dublin (DUB) to Orlando (MCO)

7.8/10 Good! (524 reviews)

Todo perfecto. Muchas Amenidades cerca.

Reviewed on 8 Jul 2026

The Delaney Hotel

South Orange

€952

per person

14 Sept - 18 Sept

found 1 day ago

Return direct flight included

Dublin (DUB) to Orlando (MCO)

9.6/10 Exceptional! (1,129 reviews)

Everyone was very nice! Property was clean. We loved the restaurant attached Highly recommend!!

Reviewed on 7 Jul 2026

Florida Hotel & Conference Center in the Florida Mall

€1,008

per person

14 Sept - 18 Sept

found 1 day ago

Return direct flight included

Dublin (DUB) to Orlando (MCO)

9.2/10 Wonderful! (1,376 reviews)

El sitio ha desmjorado algunas cosas

Reviewed on 8 Jul 2026

Riviere 3BR Apartment Stylish King Family Pets Friendly Pool & Gym Near Epic UniverseOpens

International Drive District

€1,096

per person

7 Sept - 11 Sept

found 24 hours ago

Return direct flight included

Dublin (DUB) to Orlando (MCO)

No reviews

Holiday Inn Express Orlando – South Park by IHG

€908

per person

21 Sept - 25 Sept

found 24 hours ago

Return direct flight included

Dublin (DUB) to Orlando (MCO)

9.4/10 Exceptional! (993 reviews)

The check in process was simple and quick. The room was spacious, clean, and good throughout the stay. The amenities were useful throughout the stay as well

Reviewed on 8 Jul 2026

Things to do in and around Winter Park

Winter Park, Florida, is ideal for family-friendly and entertainment-themed holidays, offering a mix of activities that include resorts, educational experiences, and vibrant shopping areas. Visitors can enjoy a variety of outdoor adventures, such as skiing and snowboarding trips, as well as mountain tours and day excursions, making it a perfect destination for those seeking both relaxation and adventure.

Shopping

Winter Park offers delightful shopping experiences at Winter Park Village, perfect for family vibes and entertainment. Edgewater Plaza Shopping Center and Colonial Plaza Mall, both just 4.8km away, are also excellent options. If you're up for a drive, consider exploring larger malls beyond this charming area.

Recreation

The Kia Centre, located 8.0km from Winter Park, offers a vibrant atmosphere for sports enthusiasts. Enjoy the thrill of live events and engage in fitness activities. The Plaza Theatre, 6.4km away, presents captivating performances, perfect for a romantic evening or family outing. Enzian Theatre, just 3.2km away, showcases independent films in a charming setting.

Adventure

Experience the thrill at AirHeads Indoor Trampoline Arena, located 11.3km from Winter Park, where you can bounce and flip amidst family-friendly vibes. For karting enthusiasts, Lil 500 Go-Karts, situated 4.8km away, offers an exhilarating ride. Challenge yourself at Aiguille Rock Climbing Center, 9.7km from Winter Park, with its outdoor climbing adventures.

Nightlife

Winter Park's nightlife is vibrant, featuring chic lounges and lively bars. Visit The Ravenous Pig for craft cocktails and a relaxed atmosphere. For a taste of live music, check out The Social, where local bands perform regularly, creating an energetic backdrop for a memorable evening out.

*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 ideal for family and city-themed vacations, offering a delightful mix of urban parks, serene lakes, and engaging art museums. Visitors can enjoy outdoor activities and cultural experiences, making it perfect for families. Don't miss the winter playground, the Winter Park Ski Resort, and the top ski resorts in the area, along with a visit to the Winter Park Visitor Centre for helpful tips on local attractions.

Orlando Science Center: Located 4.8km from Winter Park, this interactive science museum is perfect for families. It offers engaging exhibits on various scientific principles, making learning fun for all ages. With hands-on activities and live demonstrations, visitors can explore the wonders of science and technology in a vibrant atmosphere.
Full Sail University: Situated within Winter Park, this renowned university is known for its innovative programmes in arts, entertainment, and media. The campus exudes a creative vibe, making it an inspiring place for aspiring artists and professionals. Take a stroll to appreciate its architecture and artistic environment.
Orange Avenue: About 8.0km away from Winter Park, Orange Avenue is a bustling street filled with shops, restaurants, and nightlife. Experience the vibrant city vibes as you explore local eateries and enjoy live music in this lively urban setting.

Best time to go to Winter Park

The best time to visit Winter Park can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winter Park falls in August, when visitor numbers are slightly low and weather is mostly sunny with moderate rain. The coolest average temperature in Winter Park falls in January, 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.

Top hotels in Winter Park

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

Fully refundableReserve now, pay when you stay

€167

14 Jul - 15 Jul

includes taxes & fees

9.2/10 Wonderful! (6,043 reviews)

"The place was like it's own city. It was almost too big!"

Reviewed on 8 Jul 2026

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL

Fully refundableReserve now, pay when you stay

€148

19 Jul - 20 Jul

includes taxes & fees

9/10 Wonderful! (7,167 reviews)

"Its was nice staying there"

Reviewed on 8 Jul 2026

Avanti International Resort

8738 International Dr Orlando FL

Fully refundableReserve now, pay when you stay

€87

12 Jul - 13 Jul

includes taxes & fees

8/10 Very good! (4,539 reviews)

"For the price I was shocked at the amenities and the condition of the property and the rooms. My only complaint is that the onsite bar/restaurant closed kinda early but everything else was top notch. Will definitely be back."

Reviewed on 8 Jul 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.

Stay near popular Winter Park attractions

A bar with wooden decor, a TV screen, and a bartender wearing a red jersey.

Full Sail University

8.4/10 (73 reviews)

Full Sail University offers cutting-edge facilities for entertainment media and emerging technologies. Tour the professional recording studios and Hollywood-style backlot where students master creative industry skills.

See properties