Winter Garden Holidays

Book a Hotel + Flight or Car together to unlock savings

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
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Vista del Lago

While Vista del Lago isn't home to many top sights, Orange Lake Golf and Island H2O Live! are some notable places to visit nearby.

Find hotels in Vista del Lago

Top hotels in Winter Garden

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
The price is 4.675.480 ₫ per night from 8 Jul to 9 Jul
4.675.480 ₫
6.435.315 ₫ total
8 Jul - 9 Jul
includes taxes & fees
7.8/10 Good! (7,942 reviews)
"Our family had a great time."

Reviewed on 24 Jun 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
The price is 2.429.160 ₫ per night from 14 Jul to 15 Jul
2.429.160 ₫
2.732.805 ₫ total
14 Jul - 15 Jul
includes taxes & fees
9.4/10 Exceptional! (3,282 reviews)
"The property was clean and well maintained."

Reviewed on 26 Jun 2025

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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
The price is 2.442.220 ₫ per night from 13 Jul to 14 Jul
2.442.220 ₫
2.747.497 ₫ total
13 Jul - 14 Jul
includes taxes & fees
9.2/10 Wonderful! (4,150 reviews)
"Amazing"

Reviewed on 26 Jun 2025

Home2 Suites by Hilton Orlando at Flamingo Crossings
See all 53,563 properties in Winter Garden
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 Garden holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday 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're hoping to snag a cheap Winter Garden holiday package, consider visiting in February, September and October. You'll typically find lower prices on hotels and flights during these quieter months --- perfect for a budget-friendly break.
How many days is enough for Winter Garden?
When planning your Winter Garden holiday, a handful of days will be enough to tour the top spots. Make sure to stop by Carter Family Bowl --- it's one of the most popular attractions in this destination. If you're looking for more activities, consider basing yourself here and heading off on some day tours from Winter Garden.
Is it worth booking a holiday package to Winter Garden?
Well known for its cycling, markets and shopping, a Winter Garden holiday is a hit with all types of travellers. Be sure to check out leading sights like Resurrection Catholic Church and West Orange Trail, and consider renting a car for day trips to explore even more.
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 customise your search by "Property class," "Number of bedrooms," "Traveller 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 holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking accommodation 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 holiday package to Winter Garden?
If you've got your Winter Garden holiday 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. Choose when to get away: Check your diary and get your bags packed. Your favourite season and the type of activities on offer will also help you decide when to holiday in Winter Garden.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and dining out to activities and airfares. Your accommodation will likely be the largest expense during your trip to Winter Garden.
  3. Decide your trip length: Think about how much time you want to spend exploring Winter Garden. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Winter Garden holiday package that brings all your bookings together.

Popular places to visit

Flamingo Crossings Town Center

You can find the perfect gifts to bring home at Flamingo Crossings Town Center during your stay in Winter Garden. Discover the top-notch restaurants and entertainment choices in this walkable area.

Flamingo Crossings Town Center

Disney's Palm Golf Course

Enjoy a round of golf in Winter Garden at Disney's Palm Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Disney's Palm Golf Course

Disney's Magnolia Golf Course

Enjoy a round of golf in Winter Garden at Disney's Magnolia Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Disney's Magnolia Golf Course