Leesburg Vacations from $794

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Your Leesburg Vacation

With a vacation package to Leesburg, say goodbye to travel planning and hello to trouble-free adventure. Every detail of your escape has been taken care of before you depart, so you can make the most of your time discovering this fantastic city. If your trip to Leesburg includes a little sightseeing, drop by much-loved attractions like Tippecanoe Lake, Dewart Lake and Chapman Lakes. Check out Expedia's wide range of travel options and start organizing your perfect vacation to Leesburg today.

The Latest Leesburg vacation packages

Price found within the past 48 hours. Click for updated prices.
Comfort Inn La Porte

Comfort Inn La Porte

2.5 out of 5
Price was $839, price is now $794 per person
$794
per person
Sep 18 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) to South Bend (SBN)
9/10 Wonderful! (751 reviews)
Our room had an odor.

Reviewed on Jun 19, 2026

La Quinta Inn & Suites by Wyndham South Bend

La Quinta Inn & Suites by Wyndham South Bend

3 out of 5
Save 100% on your flight
Price was $1,226, price is now $860 per person
$860
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to South Bend (SBN)
7.4/10 Good! (1,000 reviews)
Standard no frills - good price

Reviewed on May 12, 2026

Biddle Point Inn & Event Venue

Biddle Point Inn & Event Venue

3 out of 5
Price was $892, price is now $813 per person
$813
per person
Sep 18 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) to South Bend (SBN)
9.6/10 Exceptional! (147 reviews)
Was looking for a last minute booking and this property was a nice surprise in terms of atmosphere, accommodations, friendliness and helpfulness of staff. Would love to return and I recommend this property

Reviewed on May 4, 2026

Super 8 by Wyndham Plymouth

Super 8 by Wyndham Plymouth

2 out of 5
Price was $858, price is now $797 per person
$797
per person
Sep 18 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) to South Bend (SBN)
8/10 Very Good! (956 reviews)
Clean room and friendly staff

Reviewed on Jun 17, 2026

The Grant Hotel and Venue

The Grant Hotel and Venue

2 out of 5
Price was $912, price is now $858 per person
$858
per person
Sep 18 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) to South Bend (SBN)
8.4/10 Very Good! (47 reviews)
Excellent, fun & great food.

Reviewed on Jun 15, 2026

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Discover the most popular places to visit in Leesburg

Tippecanoe Lake

Commune with nature and explore the great outdoors at Tippecanoe Lake during your travels in Leesburg.

Tippecanoe Lake

Leesburg Hotel Deals

3-bedroom lake front house on the Barbee Chain of Lakes in amazing Leesburg.

3-bedroom lake front house on the Barbee Chain of Lakes in amazing Leesburg.

Leesburg IN
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3-bedroom lake front house on the Barbee Chain of Lakes in amazing Leesburg.
Tippy Cottage on the Lake

Tippy Cottage on the Lake

Leesburg IN
10/10 Exceptional! (81 reviews)
"Incredible location, beautiful home and amazing host. Couldn't get much better!"

Reviewed on Jun 5, 2026

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Tippy Cottage on the Lake
“Stay Anchored” Lake Tippecanoe channel front with pier and great lake views

“Stay Anchored” Lake Tippecanoe channel front with pier and great lake views

Leesburg IN
Get rates
“Stay Anchored” Lake Tippecanoe channel front with pier and great lake views
See all 300 properties in 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.

Find the Best Leesburg Vacation Packages

Leesburg Essential Information

Language
English
Currency
U.S dollars
Population
560
Top Sights
Wagon Wheel Theatre, Lake Wawasee and Tippecanoe Lake

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Frequently asked questions

How much does a Leesburg vacation package cost?
You'll find cheap prices from $794 on Expedia for your Leesburg escape. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Leesburg costs.
What are the cheapest months to go to Leesburg?
November, December and January are the best times to search for cheap Leesburg vacation packages. Choosing to travel in less busy months means you can typically find better prices on flights and hotels.
How many days is enough for Leesburg?
Usually, a handful of days is enough to explore the major sights during your Leesburg vacation. But if you prefer to have time to kick back or go on day trips, consider extending your trip.
How to find the best Leesburg package deals?
Use Expedia's filters to find some tempting Leesburg 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 adventure for midweek, or search for Leesburg package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Leesburg vacation as a package?
You can enjoy significant savings on your Leesburg break by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Leesburg?
If you've got your Leesburg travel dates confirmed, book as soon as you can to snap up some outstanding deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for impromptu escapes.
Does Expedia offer Book Now, Pay Later Leesburg vacation packages?
Your Leesburg getaway should be a relaxing escape from your busy life, not a reason for money worries. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.