Winter Garden Vacations from $269
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Your Winter Garden Vacation
Come and discover this interesting city for yourself with a Winter Garden vacation package. Consider basing yourself in the neighborhood of Lake Buena Vista North, which is great for shopping and dining, and your time here will be nothing short of unforgettable. Like to start exploring your surroundings? West Orange Trail, Winter Garden Art Association and Winter Garden Heritage Museum are among the leading places to visit during a trip to Winter Garden. Whoever you're heading away with and whatever your budget, your ultimate Winter Garden vacation is just clicks away with Expedia.
The Latest Winter Garden vacation packages
Price found within the past 48 hours. Click for updated prices.
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See all available trips from Columbus to Winter Garden
View all tripsWhere to stay in Winter Garden
Find the best Winter Garden areas and neighborhoods for the activities you enjoy most. Learn more about Winter Garden
Oakland
When in Oakland, you can plan a visit to Winter Garden Art Association and West Orange Trail, some noteworthy sights in the nearby area.
Downtown Winter Garden
2 out of top 10 points of interest in this area
While visiting Downtown Winter Garden, you might make a stop by sights like Winter Garden Art Association and West Orange Trail.
Killarney
If you're spending some time in Killarney, Oakland Nature Preserve and Johns Lake are top sights worth seeing.
Stay near popular Winter Garden attractions
Flamingo Crossings Town Center
8.6/10 (131 reviews)
This convenient retail hub at Disney World's western gateway offers diverse shopping and dining options. Explore Target, Walgreens, and restaurants in a pedestrian-friendly environment perfect for a theme park break.
Disney's Palm Golf Course
8.4/10 (457 reviews)
This championship course winds through Florida woodlands with shimmering lakes and tropical sands. Enjoy complimentary range balls before navigating the Arnold Palmer-redesigned fairways and strategic water hazards.
Disney's Magnolia Golf Course
8.4/10 (552 reviews)
This championship course stretches through scenic magnolia trees with challenging water hazards on 11 holes. Enjoy Walt Disney-themed hole names and inspiring quotes while navigating the recently reimagined greens.
Orange County National Golf Club
8.4/10 (647 reviews)
Orange County National offers two championship courses with rolling fairways and elevation changes. Test your skills on the meticulously maintained greens or practice at the massive 42-acre circular driving range.
Surfari Water Park
9.0/10 (2,086 reviews)
Ride the waves on a dual FlowRider surf simulator or float along the 695-foot lazy river at this tropical oasis. Reserve a private cabana for a luxurious day of family fun at The Grove Resort.
West Orange Trail
8.4/10 (337 reviews)
This 22-mile paved trail winds through historic Winter Garden and natural Florida landscapes. Perfect for cyclists and walkers with charming downtown cafés and peaceful picnic spots along this scenic former railroad corridor.
Winter Garden Art Association
8.4/10 (276 reviews)
Housed in a historic firehouse, SOBO Art Gallery showcases diverse works from local Florida artists. Visitors can immerse themselves in monthly exhibits or join workshops for hands-on creative experiences.
Disney's Oak Trail Golf Course
8.4/10 (377 reviews)
This 9-hole walking course doubles as a certified Audubon Wildlife Sanctuary within Walt Disney World. Enjoy a leisurely round on rolling greens while spotting diverse Florida wildlife along the scenic fairways.
What to do in Winter Garden
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$27
per adult
92% of travellers recommend
Universal Orlando Resort Express Passes
$117
per traveler
80% of travellers recommend
Winter Garden Hotel Deals
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
$218 nightly
$245 total
Aug 25 - Aug 26
Total with taxes and fees
8/10 Very Good! (10,739 reviews)
"room service for trash , towels etc"
Reviewed on Aug 10, 2026
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
631 FLAGLER AVE Winter Garden FL
Fully refundableReserve now, pay when you stay
$74 nightly
$83 total
Aug 27 - Aug 28
Total with taxes and fees
Home2 Suites by Hilton Orlando at Flamingo Crossings
341 Flagler Ave Winter Garden FL
Fully refundableReserve now, pay when you stay
$83 nightly
$93 total
Aug 23 - Aug 24
Total with taxes and fees
9.4/10 Exceptional! (5,919 reviews)
"The room was bigger than expected. Close to the Disney attraction, at most 20 mins. We could see the fireworks at Magic Kingdom from our room."
Reviewed on Aug 10, 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.
Find the Best Winter Garden Vacation Packages
Winter Garden Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Orlando Intl. Airport (MCO) |
Population | 40,400 |
Max Temp Winter | 70ºF |
Max Temp Summer | 90ºF |
Top Sights | Walt Disney World® Resort, Universal Orlando Resort and Magic Kingdom® Park |
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Frequently asked questions
How much does a Winter Garden vacation package cost?
Offering great value package deals from $269 on Expedia, you'll be thrilled with how little a vacation to Winter Garden costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Winter Garden?
If you'd like to snag a cheap Winter Garden vacation package, consider visiting in April, May and December. You'll typically find lower prices on hotels and airfares during these months — ideal for a budget-friendly break.
How many days is enough for Winter Garden?
For a Winter Garden vacation, a handful of days will be enough to explore the highlights. Make sure to stop by Carter Family Bowl — it's one of the most popular sights in this destination. If you're looking for more activities, consider basing yourself here and going on some tours from Winter Garden.
Is it worth booking a vacation package to Winter Garden?
Winter Garden has everything you need for a memorable trip — cycling, markets and shopping are just the start. Whether you'd like to check out sights like Resurrection Catholic Church and West Orange Trail, or take the path less traveled, you'll have plenty to do on your Winter Garden vacation.
How to find the best Winter Garden package deals?
Landing a cheap Winter Garden package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, apply some filters and browse what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most affordable Winter Garden package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Winter Garden vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking accommodations and flights separately. Better still, you can tailor your Winter Garden escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Winter Garden?
If you've got your Winter Garden vacation dates locked in, book as soon as you can to bag some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Winter Garden?
- Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Winter Garden.
- Calculate your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and experiences. Your accommodations will probably be the biggest expense during your trip to Winter Garden.
- Explore Winter Garden with Expedia's trip planning tool: Gain insights into the leading attractions and best stays for your trip to Winter Garden. You can also save your favorite locations, collaborate with family and friends and manage your plans in one place.
- Decide how long to go for: Now that you're up to speed on Winter Garden, you can work out the right length of your vacation. Put together a rough plan and allocate enough time for all the things you want to do.
- Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customized Winter Garden vacation package.
- Book experiences or activities in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on the highlights of Winter Garden. Find all the exciting things to do in Winter Garden in Winter Garden with our dedicated activity guide.
Does Expedia offer Book Now, Pay Later Winter Garden vacation packages?
Set off on your ideal getaway to Winter Garden with Expedia's Book Now, Pay Later vacations. There's no need to save up or hold off until payday — we've joined forces with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snap up travel deals while they last.
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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.
