An aerial view of a city with a prominent building complex, surrounded by dense greenery and a river.

Maitland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

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

  • Rest easy

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

Your Maitland Vacation

Lock in a Maitland vacation package that has everything you need and nothing you don't. Good for dining, bars and pubs and shopping, think about basing yourself in the neighborhood of Ivanhoe Village. Make your trip to Maitland even more fun by including some sightseeing. Rollins College, Full Sail University and Altamonte Mall are among the leading attractions you'll want to explore. Expedia is here to help you escape the everyday. Tailor your vacation to Maitland to suit your style of travel, whatever that may be!

Top Maitland vacation deals

Price found within the past 48 hours. Click for updated prices.
  • A water park with slides and water features.
    Jan 9 - Jan 15

    Westgate Town Center Resort + Flight

    Kissimmee
    6 nights
    4.0 star property
    8.4/10 - Very good (2,080 reviews)
    "The new rooms are good"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    CA $1,122
    CA $590
    per traveller
    found 1 day ago
    Westgate Town Center Resort
  • A resort with multiple buildings, a central pool area, a beach, and a dock with a boat.
    Dec 18 - Dec 23

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,000 reviews)
    Roundtrip • Hamilton (YHM) - Orlando (MCO)
    YHM - MCO • Nonstop MCO - YHM • Nonstop
    Save 100% on your flight
    CA $2,415
    CA $1,358
    per traveller
    found 18 hours ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • A deck with lounge chairs and tables overlooking a beach with palm trees and ocean waves.
    Jan 24 - Jan 28

    Westgate Cocoa Beach Resort + Flight

    Cocoa Beach
    4 nights
    4.0 star property
    8.6/10 - Excellent (578 reviews)
    "The beaches across the street. The pools are nice however I had a room right next to the pool and they play music up until 9:00pm at night. So if you just trying to rest that will not happen. The music just kept playing all day long."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    Save 100% on your flight
    CA $1,703
    CA $966
    per traveller
    found 1 day ago
    Westgate Cocoa Beach Resort
  • An aerial view of a curved swimming pool with lounge chairs and umbrellas around it.
    Jan 15 - Jan 21

    Meliá Orlando Celebration + Flight

    Celebration
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,645 reviews)
    Roundtrip • Toronto (YTO) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    CA $1,659
    CA $974
    per traveller
    found 1 day ago
    Meliá Orlando Celebration
  • A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.
    Jan 31 - Feb 5

    Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort + Flight

    Kissimmee
    5 nights
    2.0 star property
    9.0/10 - Wonderful (4,109 reviews)
    "My bueno"
    Reviewed November 9, 2026
    Roundtrip • Halifax (YHZ) - Orlando (MCO)
    YHZ - MCO • Nonstop MCO - YHZ • Nonstop
    CA $1,524
    CA $946
    per traveller
    found 1 day ago
    Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort

Discover the most popular places to visit in Maitland

A marquee with "ENZIAN CINEMA CAFE" and "MORE THAN A MOVIE" written on it.
Photo by Visit Orlando
Open Photo by Visit Orlando

Enzian Theater

6.4/10 (21 reviews)
Wine and dine as you watch a movie in a unique cinema that's set out like a large dining room.
See properties

What to do in Maitland

Orlando: The Pinball Palace at Dezerland Park

The Pinball Palace at Dezerland Park Admission

CA $14
per adult
90% of travellers recommend
The Pinball Palace at Dezerland Park Admission
See all activities in Maitland

Maitland Hotel Deals

A spacious lobby with a high glass ceiling, a bar area, and seating arrangements.

Sheraton Orlando North Hotel

Sheraton Orlando North Hotel
3.5 star property
2.8 km from Maitland
8.4 out of 10, Very good, (1,480 reviews)
"Very nice, impeccably clean hotel, great stay!"
The price is CA $125
CA $140 total
includes taxes & fees
Nov 29 - Nov 30
Sheraton Orlando North Hotel
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.
See all properties in Maitland

Frequently Asked Questions

How much does a Maitland vacation package cost?

Offering excellent value package deals from CA $590 on Expedia, you'll be surprised at how little a vacation to Maitland costs! Our packages simplify travel planning and maximize your savings.

What are the cheapest months to go to Maitland?

July, September and November are great times to search for cheap Maitland vacation packages. Choosing to travel in less busy months means you can typically find lower prices on hotels and flights.

How many days is enough for Maitland?

To fully enjoy your Maitland vacation, we suggest staying for 3 days. Split your time between discovering Lake Eola Park, Altamonte Mall and other well-known attractions, on top of exploring neighbourhoods like Northeast Orlando and Ivanhoe Village. If you've got some time to spare, add a day trip to your Maitland vacation itinerary.

Is it worth booking a vacation package to Maitland?

Maitland has everything you need for an unforgettable trip. Begin your Maitland vacation on a high note by visiting major attractions like Maitland Art Centre.

How to find the best Maitland package deals?

Use Expedia's filters to help you find some fabulous Maitland package deals. When you start your search, simply 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 search for Maitland package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.

Is it cheaper to book a Maitland vacation as a package?

You can enjoy significant savings on your next Maitland break by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.

When to book a vacation package to Maitland?

Land amazing discounts by reserving your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Maitland getaway.

How to plan a trip to Maitland?

  1. Pick your travel dates: The things you want to do in Maitland and your preferred season will help you decide when to get away.
  2. Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Maitland.
  3. Decide how long to go for: Now that you're more familiar with Maitland, you can work out the perfect length of your vacation. Create a rough itinerary and give yourself enough time to cover everything you want to do.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Maitland 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.