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Featured Holiday Homes in Leesburg

Lakeside Indiana Vacation Rental Near Fort Wayne!

Lakeside Indiana Vacation Rental Near Fort Wayne!

Churubusco
With a stay at this vacation home in Churubusco, you'll be near the beach, and 6.9 mi (11.1 km) from Chain O' Lakes State Park and 9.5 mi (15.3 km) from Parkview ...
Lakeside Indiana Vacation Rental Near Fort Wayne!
Lakefront Syracuse Home w/ Deck & Private Dock!

Lakefront Syracuse Home w/ Deck & Private Dock!

Syracuse
With a stay at this vacation home in Syracuse, you'll be steps from Syracuse Lake and a 2-minute drive from Creative Fish Art Gallery & ArtZie Workshop.
Lakefront Syracuse Home w/ Deck & Private Dock!
Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath

Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath

North Webster
Located in North Webster, this vacation home is on the waterfront, within a 15-minute drive of Webster Lake and Big Barbee Lake.
Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath
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Tranquil lakeside retreat

Tranquil lakeside retreat

Syracuse
Located in Syracuse, this vacation home is on a lake, a 3-minute drive from Lake Wawasee and 8 minutes from South Shore Golf Club.
Tranquil lakeside retreat
Barbee Lake Big House!  Sleeps 14+ Game Garage!  Pier and Dock to Barbee!

Barbee Lake Big House! Sleeps 14+ Game Garage! Pier and Dock to Barbee!

Warsaw
Located in Warsaw, this vacation home is on the waterfront, a 1-minute drive from Big Barbee Lake and 6 minutes from Tippecanoe Lake.
Barbee Lake Big House! Sleeps 14+ Game Garage! Pier and Dock to Barbee!
Charming farmhouse in peaceful countryside

Charming farmhouse in peaceful countryside

Nappanee
Located in Nappanee, this vacation home is in a rural location, within a 15-minute drive of McCormick Creek Golf Course and Coppes Commons.
Charming farmhouse in peaceful countryside
Lake Wawasee Escape: private pool, hot tub, pier, kayaks & paddleboat!!!

Lake Wawasee Escape: private pool, hot tub, pier, kayaks & paddleboat!!!

Syracuse
Located in Syracuse, this vacation home is on the waterfront, a 1-minute drive from Lake Wawasee and 7 minutes from Wawasee Golf Club.
Lake Wawasee Escape: private pool, hot tub, pier, kayaks & paddleboat!!!
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres

Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres

Goshen
With a stay at this vacation home in Goshen, you'll be within a 15-minute drive of Coppes Commons and Amish Acres.
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres
`Burning Pine Inn' Farm House in Amish country.

`Burning Pine Inn' Farm House in Amish country.

Middlebury
Located in Goshen, this vacation home is in a rural location, within a 15-minute drive of Elkhart County Fairgrounds and Sprocket Dog Park.
`Burning Pine Inn' Farm House in Amish country.
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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.

Leesburg Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Leesburg vacation homes are the perfect way for you to wing it.

Holiday houses in Leesburg let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Leesburg in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Leesburg adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Leesburg with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Leesburg vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Leesburg Holiday Homes essential information

Accommodation
83 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Lakeside Indiana Vacation Rental Near Fort Wayne!, Lakefront Syracuse Home w/ Deck & Private Dock!, Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath, Tranquil lakeside retreat , Barbee Lake Big House! Sleeps 14+ Game Garage! Pier and Dock to Barbee!, Charming farmhouse in peaceful countryside, Lake Wawasee Escape: private pool, hot tub, pier, kayaks & paddleboat!!!, Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres, `Burning Pine Inn' Farm House in Amish country.

Top trending hotels in Leesburg

Beautiful lakefront property

Beautiful lakefront property

Leesburg
Located in Leesburg, this cottage is on the waterfront, a 3-minute drive from Tippecanoe Lake and 6 minutes from Big Barbee Lake.
Beautiful lakefront property
beautiful cottage by the lake. Relax and enjoy your stay.

beautiful cottage by the lake. Relax and enjoy your stay.

Leesburg
Located in Leesburg, this cottage is on a lake, a 1-minute drive from Tippecanoe Lake and 8 minutes from Chapman Lakes.
beautiful cottage by the lake. Relax and enjoy your stay.
Lake Tippecanoe Lake House - Anchor Inn

Lake Tippecanoe Lake House - Anchor Inn

Leesburg
Located in Leesburg, this vacation home is on the waterfront, a 1-minute drive from Tippecanoe Lake and 7 minutes from Dewart Lake.
Lake Tippecanoe Lake House - Anchor Inn
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Wyndham Garden Warsaw

Wyndham Garden Warsaw

3 out of 5
2519 E Center St, Warsaw, IN
When you stay at Wyndham Garden Warsaw in Warsaw, you'll be 24 mi (38.6 km) from Amish Acres.
Wyndham Garden Warsaw
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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.

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^Subject to availability and chosen travel dates.