Winter Garden Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.

Top Winter Garden Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8/10 Very Good! (1,274 reviews)
The property was nice, lots of things to do for everyone. However the shipwreck water park wasn’t included you have to pay for that separately. Also, be prepared to pay additional resort fees at the property.

Reviewed on Jul. 11, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Sep 15 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Good choice to stay, close to universal and not that far from disney. I would definetly recomend it. Excelent service.

Reviewed on Jul. 10, 2025

ette hotel

ette hotel

5 out of 5
per person
Sep 15 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9.8/10 Exceptional! (310 reviews)
very friendly helpful staff. nice area with many restaurants and grocery stores around. clean rooms. elegant hotel

Reviewed on Jul. 4, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.2/10 Very Good! (5,060 reviews)
Quality customer service

Reviewed on Jul. 11, 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Save 100% on your flight
per person
Sep 15 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9.6/10 Exceptional! (1,000 reviews)
Nice nights stay . Good bar but a little out of way for downtown

Reviewed on Jul. 9, 2025

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
Default Image

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

Ready to book your vacation to Winter Garden?

 

Choose your dates

Winter Garden Hotel Deals

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 CA $203 per night from Jul 15 to Jul 16
CA $203
CA $290 total
Jul 15 - Jul 16
includes taxes & fees
7.8/10 Good! (8,076 reviews)
"Overall we had a wonderful vacation at The Grove resort and water park. Something to consider is you get a great suite and access to pools and waterpark area but literally everything else has a fee attached. We stayed 8 nights and everything from parking, any cleaning service, any additional activities ..."

Reviewed on Jul. 11, 2025

The Grove Resort & Water Park Orlando
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 CA $150 per night from Jul 27 to Jul 28
CA $150
CA $168 total
Jul 27 - Jul 28
includes taxes & fees
9.2/10 Wonderful! (4,229 reviews)
"Good stay, only thing I didn’t like, you didn’t know about paying for parking until you got there, might have stayed somewhere else"

Reviewed on Jul. 10, 2025

Home2 Suites by Hilton Orlando at Flamingo Crossings
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 CA $127 per night from Jul 28 to Jul 29
CA $127
CA $143 total
Jul 28 - Jul 29
includes taxes & fees
9.4/10 Exceptional! (3,405 reviews)
"Keriann was awesome!!!!!"

Reviewed on Jul. 11, 2025

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
See all 53,619 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Winter Garden

Flamingo Crossings Town Center

You can do some window-shopping at Flamingo Crossings Town Center during your visit to Winter Garden. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Flamingo Crossings Town Center

Surfari Water Park

4.5/5(50 reviews)

Enjoy a fun-filled day at Surfari Water Park as part of your trip to Four Corners. Make time for the shops and golf courses in this family-friendly area.

Surfari Water Park

Central Florida Railroad Museum

You can study the exhibits at Central Florida Railroad Museum, a museum with a story of its own, during your travels to Winter Garden. Amble around this family-friendly area's lakeside, or seek out the adventure tours.

Central Florida Railroad Museum

What to do in Winter Garden

2014_AQ_KatasKookaburraCove_D4D_0772.jpg

Aquatica Orlando

CA $74
per traveller
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $116
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Indoor Karting

Andretti Indoor Karting & Games in Orlando

CA $42
per adult
80% of travellers recommend
Andretti Indoor Karting & Games in Orlando
See all activities in Winter Garden

Frequently asked questions

How much does a Winter Garden vacation package cost?
You can grab a vacation package to this destination from CA $635 on Expedia. But how much your vacation to Winter Garden costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Winter Garden?
You're likely to find lower prices and greater availability in February, September and October. Browse our cheap Winter Garden vacation packages and you could get some great off-season deals.
How many days is enough for Winter Garden?
You can visit all the major attractions in Winter Garden in a few days, including the popular Winter Garden Art Association. If you're after a longer Winter Garden vacation, check out what kind of activities and excursions are available in the area.
Is it worth booking a vacation package to Winter Garden?
Winter Garden has everything you need for a fantastic break --- cycling, markets and shopping are just the start. Whether you want to visit sights such as Resurrection Catholic Church and West Orange Trail, or venture off the beaten track, you'll have plenty to experience on your Winter Garden vacation.
How to find the best Winter Garden package deals?
Finding a cheap Winter Garden package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, add a few filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" 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 often lower.
Is it cheaper to book a Winter Garden vacation as a package?
You can enjoy significant savings on your Winter Garden break by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winter Garden?
Score incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Winter Garden escape.
How to plan a trip to Winter Garden?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred time of year and the available activities will also help you decide when to visit Winter Garden.
  2. Set your budget: Consider costs like flights, meals and transportation when working out how much to save for your trip to Winter Garden. Then, select a hotel that suits your budget, whether that's a low-cost option or a high-end getaway.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Winter Garden. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Winter Garden vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.