Winter Park Holidays

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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

If you're looking for some top things to see and do in Baldwin Park and surrounding area, you can visit Orlando Fashion Square and East Orlando Shopping Center.

Find hotels in Baldwin Park

Top hotels in Winter Park

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 S$149 per night from 10 Jul to 11 Jul
S$149
10 Jul - 11 Jul
includes taxes & fees
8.8/10 Excellent! (2,527 reviews)
"Beautiful property. My family loved how big the one bedroom was and how close it is to Sea World and good eats."

Reviewed on 18 Jun, 2025

Marriott's Grande Vista
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 S$169 per night from 10 Jul to 11 Jul
S$169
10 Jul - 11 Jul
includes taxes & fees
9.2/10 Wonderful! (3,067 reviews)
Family vacation
"The staff for super friendly and helpful it's a little hard finding stuff in the place cuz it's so big but anytime I seen someone that work there and had to ask for directions they were super helpful. The only thing I didn't like is I had two different rooms during my stay cuz I booked an extra day ..."

Reviewed on 19 Jun, 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Rosen Inn Lake Buena Vista
Rosen Inn Lake Buena Vista
3.5 out of 5
8442 Palm Parkway, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is S$89 per night from 22 Jul to 23 Jul
S$89
22 Jul - 23 Jul
includes taxes & fees
8.4/10 Very Good! (5,163 reviews)
"Great location!"

Reviewed on 19 Jun, 2025

Rosen Inn Lake Buena Vista
See all 14,477 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.

Frequently asked questions

How much does a Winter Park holiday package cost?
You'll find cheap prices 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?

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

Popular places to visit

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What to do in Winter Park

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

S$98
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Old Town Kissimmee: Attraction and Meal Combo Offers

Old Town Kissimmee: Attraction and Meal Combo Offers

S$19
per adult
80% of travellers recommend
Old Town Kissimmee: Attraction and Meal Combo Offers
Indoor Karting

Andretti Indoor Karting & Games in Orlando

S$40
per adult
80% of travellers recommend
Andretti Indoor Karting & Games in Orlando
See all activities in Winter Park

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.