Winter Springs Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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Your Winter Springs Vacation

Say bye-bye to the worries of planning and hello to a Winter Springs vacation package. With everything organized before you leave, you can focus on discovering the best of this city, starting with Ivanhoe Village, which is great for dining, bars and pubs and shopping. If taking in sights is on the cards during your trip to Winter Springs, swing by leading attractions like Altamonte Mall, Winter Park Village and Cranes Roost Park. Your Winter Springs vacation is a couple of clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored just for you.

Top Winter Springs Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,523, price is now CA $859 per person
CA $859
per person
Jan 1 - Jan 8
found 17 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very good! (2,105 reviews)
The property is very nice but wish the staff are more helpful.

Reviewed on Nov 1, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was CA $3,309, price is now CA $1,717 per person
CA $1,717
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was CA $2,229, price is now CA $1,266 per person
CA $1,266
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Orlando (MCO)
8.6/10 Excellent! (572 reviews)
Great family stay

Reviewed on Oct 31, 2026

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was CA $2,286, price is now CA $1,304 per person
CA $1,304
per person
Jan 1 - Jan 8
found 17 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.6/10 Exceptional! (1,234 reviews)

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was CA $1,806, price is now CA $1,051 per person
CA $1,051
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9/10 Wonderful! (4,064 reviews)
.

Reviewed on Oct 31, 2026

Ready to book your vacation to Winter Springs?

 

Choose your dates

Winter Springs Hotel Deals

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $306 per night from Nov 23 to Nov 24
CA $306
CA $344 total
Nov 23 - Nov 24
includes taxes & fees
Hyatt Regency Orlando International Airport
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd Orlando FL
Fully refundable
The price is CA $129 per night from Nov 16 to Nov 17
CA $129
CA $146 total
Nov 16 - Nov 17
includes taxes & fees
DoubleTree by Hilton at the Entrance to Universal Orlando
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Nov 2 to Nov 3
CA $212
CA $239 total
Nov 2 - Nov 3
includes taxes & fees
9/10 Wonderful! (7,815 reviews)
"We really enjoyed it. We stayed in beachside which was closest to the Volcano Bay entrance. It was about a 5 min walk to the main entrance where everything is but not too bad. I'd prefer to be centrally located. The room was very nice and accommodating. I wish the bathrooms had blowers but other ..."

Reviewed on Nov 1, 2026

Universal's Cabana Bay Beach Resort
See all 5,366 properties in Winter Springs
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

Stay near popular Winter Springs attractions

A curved concrete path leading to a dock over a calm lake, surrounded by lush greenery and tall trees with Spanish moss.

Central Winds Park

After visiting Central Winds Park, make a plan to see the other sights and activities in Winter Springs. Amble around the area's lakeside or attend a sporting event.
See properties

What to do in Winter Springs

Simulated Shooting Range

Bill Drill: All-Ages Tactical Adventure in Orlando

CA $140
per adult
100% of travellers recommend
Bill Drill: All-Ages Tactical Adventure in Orlando
Orlando Science Center General Admission Ticket

Orlando Science Center General Admission Ticket

CA $41
per adult
80% of travellers recommend
Orlando Science Center General Admission Ticket
Simulated Shooting Range

Basic Drill: Introductory Indoor Tactical Experience Orlando

CA $97
per adult
100% of travellers recommend
Basic Drill: Introductory Indoor Tactical Experience Orlando
See all activities in Winter Springs

Frequently asked questions

How much does a Winter Springs vacation package cost?
You'll find cheap prices from CA $859 on Expedia for your Winter Springs getaway. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Winter Springs costs.
What are the cheapest months to go to Winter Springs?
Travel in the low or shoulder season and you're likely to get cheap Winter Springs vacation packages. Bear in mind that school vacation periods and major festivals and events can have an impact on prices, so do a little research before you go.
How many days is enough for Winter Springs?
Typically, a handful of days is enough to check out the major sights during your Winter Springs vacation. However, if you prefer to have some time to relax or take day tours, consider extending your itinerary.
Is it worth booking a vacation package to Winter Springs?
Winter Springs has everything you need for an amazing escape. Begin your Winter Springs vacation on a high note by checking out popular attractions like Central Winds Park.
How to find the best Winter Springs package deals?
Use Expedia's filters to help you find some great Winter Springs package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Winter Springs package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Winter Springs vacation as a package?
You can enjoy significant savings on your next Winter Springs retreat by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Winter Springs?
If you have your Winter Springs travel dates finalized, book early to bag some outstanding deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Winter Springs?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Winter Springs.
  2. Budget wisely: In addition to the cost of your hotel, you should consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Winter Springs.
  3. Decide how many days away: Start by compiling a list of the activities and sights you'd like to experience in Winter Springs. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Winter Springs 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.