Winter Garden Vacations from $194

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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.
Palazzo Lakeside Hotel
Westgate Lakes Resort & Spa Universal Studios Area
Westgate Town Center Resort
Seasons Florida Resort
ette hotel
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Where to stay in Winter Garden

Find the best Winter Garden areas and neighborhoods for the activities you enjoy most. Learn more about Winter Garden

Discover the most popular places to visit in Winter Garden

What to do in Winter Garden

Winter Garden Hotel Deals

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
341 Flagler Ave, Winter Garden, FL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from Aug 24 to Aug 25
$123 total
Aug 24 - Aug 25
Total includes taxes and fees
9.2/10 Wonderful! (4,420 reviews)
"Pros: family friendly, nice pool, close to Disney Cons: busy buffet breakfast area, not a lot of fresh fruit or breakfast meat choices."

Reviewed on Aug 10, 2025

Home2 Suites by Hilton Orlando at Flamingo Crossings
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $201 total per night from Aug 13 to Aug 14
$201 total
Aug 13 - Aug 14
Total includes taxes and fees
7.8/10 Good! (8,296 reviews)
"Very good, I recommend."

Reviewed on Aug 9, 2025

The Grove Resort & Water Park Orlando
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

2.5 out of 5
631 FLAGLER AVE, Winter Garden, FL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $105 total per night from Aug 26 to Aug 27
$105 total
Aug 26 - Aug 27
Total includes taxes and fees
9.4/10 Exceptional! (3,614 reviews)
"Excellent!"

Reviewed on Aug 9, 2025

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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.

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Frequently asked questions

How much does a Winter Garden vacation package cost?
Offering great value package deals from $194 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.