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A park with a pond, a wooden bridge, and trees.

Leesburg 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

Top Leesburg vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Reception
    Sept 24 - Sept 30

    Seasons Florida Resort + Flight

    Kissimmee
    6 nights
    2.0 star property
    9.0/10 - Wonderful (3,728 reviews)
    "The AC worked very well. The parking area and surrounding property gave a good sense of security."
    Reviewed July 20, 2026
    Roundtrip • Toronto (YTO) - Orlando (MCO)
    YYZ - MCO • 1 stop MCO - YYZ • 1 stop
    CA $973
    CA $591
    per traveller
    found 1 day ago
    Seasons Florida Resort
  • In-room safe, laptop workspace, blackout drapes, iron/ironing board
    Aug 26 - Aug 31

    Palazzo Lakeside Hotel + Flight

    Kissimmee
    5 nights
    3.0 star property
    8.4/10 - Very good (5,241 reviews)
    "Breakfast was just okay"
    Reviewed July 21, 2026
    Roundtrip • Toronto (YTO) - Orlando (MCO)
    YYZ - MCO • 1 stop MCO - YYZ • 1 stop
    CA $1,550
    CA $617
    per traveller
    found 21 hours ago
    Palazzo Lakeside Hotel
  • Terrace/patio
    Sept 2 - Sept 8

    Westgate Palace Hotel / Universal / I-Drive + Flight

    International Drive District
    6 nights
    4.0 star property
    9.0/10 - Wonderful (1,293 reviews)
    "Located in a central location that is very close to most theme parks. Staff was friendly, the resort was very clean and comfortable. Highly recommended!"
    Reviewed July 20, 2026
    Roundtrip • Toronto (YTO) - Orlando (MCO)
    YTZ - MCO • 1 stop MCO - YYZ • Nonstop
    CA $1,878
    CA $881
    per traveller
    found 1 day ago
    Westgate Palace Hotel / Universal / I-Drive
  • Sundeck
    Sept 1 - Sept 6

    Westgate Cocoa Beach Resort + Flight

    Cocoa Beach
    5 nights
    4.0 star property
    8.6/10 - Excellent (555 reviews)
    "The setup of the hotel is strange, there a different section of the hotel for you to stay, but if you are not familiar with the hotel, you might ask yourself, why you ended up in the from section of the hotel, facing the road, and not the pool area. If you decide to sleep late, this is not the hotel for you, since noises are coming from all over the place, my las 2 mornings, it was 8:30 and there was already workers all over the place being loud, and the noise from the room above it is expected..."
    Reviewed July 9, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • 2 stops
    CA $2,756
    CA $1,551
    per traveller
    found 1 day ago
    Westgate Cocoa Beach Resort
  • Water park
    Sept 24 - Sept 30

    Westgate Lakes Resort & Spa Universal Studios Area + Flight

    Orlando
    6 nights
    4.0 star property
    8.4/10 - Very good (6,731 reviews)
    "Water park is alot smaller than the pictures. Discount for the park was over price for the size."
    Reviewed July 20, 2026
    Roundtrip • Toronto (YTO) - Orlando (MCO)
    YYZ - MCO • 1 stop MCO - YYZ • 1 stop
    CA $1,247
    CA $742
    per traveller
    found 1 day ago
    Westgate Lakes Resort & Spa Universal Studios Area

Discover the most popular places to visit in Leesburg

An aerial view of a golf course with sand bunkers and trees.

Plantation Golf Club

8.0/10 (32 reviews)
Enjoy a round of golf in Leesburg at Plantation Golf Club. Stroll along the lakeside or experience the area's festivals.

Leesburg Hotel Deals

Property amenity

TownePlace Suites by Marriott Leesburg

TownePlace Suites by Marriott Leesburg
3.0 star property
1.4 km from Leesburg
9.0 out of 10, Wonderful, (391 reviews)
"This is not my first time that I’ve stayed there. I would recommend this place. I’ve stayed there by myself and also with family very safe and secure location beautiful steak restaurant one minute walking away to it."
The price is CA $147
CA $163 total
includes taxes & fees
Jul 26 - Jul 27
TownePlace Suites by Marriott Leesburg
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 Leesburg

Frequently Asked Questions

How much does a Leesburg vacation package cost?

Offering excellent value package deals from CA $591 on Expedia, you'll be thrilled with how little a vacation to Leesburg costs! Expedia's packages simplify travel planning and maximize your savings.

What are the cheapest months to go to Leesburg?

You can typically find lower rates and better availability in June, August and September. Take a look at our cheap Leesburg vacation packages and you could land some great off-season discounts.

How many days is enough for Leesburg?

Typically, a few days is enough for a Leesburg vacation. With a well-organized itinerary, you can check out all the main sights including ViaPort Florida, as well as explore some hidden treasures along the way.

How to find the best Leesburg package deals?

Start your search for a Leesburg package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Leesburg package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Leesburg adventure underway.

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

Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still get the freedom to create a tailored Leesburg vacation by choosing your preferred type of stay, airline and car class.

When to book a vacation package to Leesburg?

If you have your Leesburg vacation dates locked in, book as soon as you can to bag some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for quick escapes.

How to plan a trip to Leesburg?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Leesburg.
  2. Set a budget: Factor in costs like transportation, flights and meals when calculating how much to save for your trip to Leesburg. Then, select a hotel that suits your budget, whether that's an economical option or a deluxe retreat.
  3. Work out your trip length: Think about how much time you want to spend exploring Leesburg. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Leesburg vacation package that brings all your bookings together.