Leesburg Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Leesburg vacation rentals

Fridge, microwave, oven, stovetop
Tippecanoe Lakefront Classic Cottage

Tippecanoe Lakefront Classic Cottage

Tippecanoe Lakefront Classic Cottage
Leesburg
The price is ￥35,372
￥81,459 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Tippecanoe Lakefront Classic Cottage
Interior
Welcome to our Home in Ligonier

Welcome to our Home in Ligonier

Welcome to our Home in Ligonier
2.0 star property
Ligonier
10.0 out of 10, Exceptional, (2)
"This is our third time renting this property. The hosts are awesome and pay attention to detail. Couldn't be happier with our stay!"
United States
Jeremiah A.
The price is ￥17,933
￥37,900 total
includes taxes & fees
Dec 27 - Dec 28
Welcome to our Home in Ligonier
Property grounds
Fishing · Kayaks · Firepit · Paddleboat

Fishing · Kayaks · Firepit · Paddleboat

Fishing · Kayaks · Firepit · Paddleboat
Pierceton
10.0 out of 10, Exceptional, (22)
"Clean property, gewat location, loved the lake and the stars."
United States
joseph b.
The price is ￥17,595
￥38,673 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Fishing · Kayaks · Firepit · Paddleboat
Exterior
3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain

3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain

3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain
Pierceton
9.6 out of 10, Exceptional, (14)
"This isn't our first time staying here and we love it. It's easy to find, simple living and quiet. Also, there is food delivery available so we don't have to cook after a long hunt."
United States
Michael G.
The price is ￥27,290
￥55,016 total
includes taxes & fees
Dec 28 - Dec 29
3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain
Microwave, oven, stovetop
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Syracuse
9.8 out of 10, Exceptional, (7)
"Great clean little cabin by the lake. Hot tub and outdoor area is nice! Very private with a view of the water on the porch. "
United States
Ty M.
The price is ￥20,116
￥40,694 total
includes taxes & fees
Dec 30 - Dec 31
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Exterior
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
Warsaw
10.0 out of 10, Exceptional, (17)
"Wonderful home, lovely views on the lake, great communication with owner and host. We very much enjoyed our stay!"
United States
Carol B.
The price is ￥24,870
￥48,838 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
Exterior
Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake
Winona Lake
9.8 out of 10, Exceptional, (38)
"Nice, clean, fully updated, little cottage with all amenities in a quaint little village. Perfect place to stay for our weekend getaway. Everyone we met was so friendly and polite. If staying be sure to stop at Trailhouse and rent a bike!"
United States
Jesse G.
The price is ￥20,350
￥40,957 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Trail Side in the Heart of Winona Lake
Dining
Woodside Retreat in the Heart of Amish Country

Woodside Retreat in the Heart of Amish Country

Woodside Retreat in the Heart of Amish Country
Nappanee
10.0 out of 10, Exceptional, (11)
"It was a very unique place to stay for a few days. Very clean and thoughtful in items provided"
United States
VICKI
The price is ￥17,933
￥30,868 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Woodside Retreat in the Heart of Amish Country
Terrace/patio
Charming farmhouse in peaceful countryside

Charming farmhouse in peaceful countryside

Charming farmhouse in peaceful countryside
Nappanee
10.0 out of 10, Exceptional, (165)
"The farmhouse is wonderfully updated and is quiet and comfortable. "
United States
Brent L.
The price is ￥15,438
￥24,861 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Charming farmhouse in peaceful countryside
Interior
Heart Jacuzzi · Kayaks · Firepit · Pier

Heart Jacuzzi · Kayaks · Firepit · Pier

Heart Jacuzzi · Kayaks · Firepit · Pier
Warsaw
10.0 out of 10, Exceptional, (11)
"Was a wonderful weekend get-away for the wife and I. Quiet, relaxing, and stress free but with everything we needed. "
United States
Ed R.
The price is ￥21,520
￥43,745 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Heart Jacuzzi · Kayaks · Firepit · Pier
Outdoor pool
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Milford
10.0 out of 10, Exceptional, (29)
"We had a really great time and the host was very very responsive to all our questions. "
United States
Mary B.
The price is ￥21,052
￥56,937 total
includes taxes & fees
Dec 29 - Dec 30
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Smart TV, video games
Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!

Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!

Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!
Goshen
9.6 out of 10, Exceptional, (16)
"Location was convenient for biking the the Pumpkin Vine Trail."
United States
Jon C.
The price is ￥24,589
￥44,519 total
includes taxes & fees
Dec 28 - Dec 29
Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!
Property grounds
3-BR + Firepit, Coffee Bar & Grill

3-BR + Firepit, Coffee Bar & Grill

3-BR + Firepit, Coffee Bar & Grill
Bourbon
10.0 out of 10, Exceptional, (1)
"Our stay was perfect, starting with communication, spotless, decorated for FALL and it felt like we were at home! Our son’s college was 24 minutes from the house and it worked out perfect for him to come visit and us enjoy Family Weekend at the school to watch him play baseball! Our next visit will be this exact place! We hope to get to come at Christmas because we want to see how beautiful it’s decorated in Christmas! 10/10 stay! Sweetest Host! The basket of smores and apples was the best! "
United States
Brandy T.
3-BR + Firepit, Coffee Bar & Grill
Dining
The Heron House @Waldron Lake

The Heron House @Waldron Lake

The Heron House @Waldron Lake
Wawaka
9.8 out of 10, Exceptional, (31)
"We had an absolutely fantastic time! We loved every minute of it and will definitely be back soon. "
United States
Jimmy L.
The price is ￥42,416
￥98,155 total
includes taxes & fees
Jan 13 - Jan 14, 2026
The Heron House @Waldron Lake
Property grounds
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
Leesburg
10.0 out of 10, Exceptional, (1)
"Fantastic place to get away right on the water. Enjoyed our 3 day stay with my husband and our puppy. There is a fenced in yard and a dock. Wonderful place to relax. Our host was very helpful and easy to get in touch with.Recommend highly "
United States
Lenora F.
The price is ￥38,985
￥79,816 total
includes taxes & fees
Dec 26 - Dec 27
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
Dining
Private Lake Front Home on Wawasee - Exclusive and Quiet Ogden Island Retreat

Private Lake Front Home on Wawasee - Exclusive and Quiet Ogden Island Retreat

Private Lake Front Home on Wawasee - Exclusive and Quiet Ogden Island Retreat
Syracuse
10.0 out of 10, Exceptional, (2)
"Great views, spacious, clean home, responsive owner. "
United States
Bob T.
The price is ￥47,250
￥85,405 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Private Lake Front Home on Wawasee - Exclusive and Quiet Ogden Island Retreat
Fridge, microwave, oven, dishwasher
Hilltop Family Retreat

Hilltop Family Retreat

Hilltop Family Retreat
Goshen
10.0 out of 10, Exceptional, (1)
"Property appears to be recently remodeled and up to date with plenty of space for large groups. 3 bathrooms so no one has to wait. Upstairs can be warm during the summer but nothing a fan doesn't fix. Property owner is responsive and easy to reach."
United States
George M.
The price is ￥64,325
￥95,700 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hilltop Family Retreat
Dining
Rock Run Creek House

Rock Run Creek House

Rock Run Creek House
Goshen
10.0 out of 10, Exceptional, (3)
"was a fantastic rental. Thank you so much!"
United States
Lavern Y.
The price is ￥75,475
￥110,523 total
includes taxes & fees
Dec 29 - Dec 30
Rock Run Creek House
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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Top Leesburg Hotel Reviews

Tru by Hilton Warsaw

Tru by Hilton Warsaw

10/10 Excellent
"Breakfast leaves a lot to be desired! The staff appearance could be improved location is okay for traveling one nighter"
penny 2-night trip
Posted 4 days ago
Tru by Hilton Warsaw

Find out more about Leesburg

Search for holiday rentals in Leesburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Leesburg using one of the methods below:

  • View our selection of featured holiday rentals in Leesburg
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  • Enter your travel dates to view the best deals on holiday rentals in Leesburg while they last

Look no further and take a look at our great range of rental properties in Leesburg!

Frequently asked questions

Are there vacation rentals in Leesburg?

Yes, you can find vacation rentals near well known sights in Leesburg, or you can go with a secluded option if you're looking for relaxation.

What's the top vacation rental that Leesburg has to offer?

Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks: Visitors like this Leesburg vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Leesburg?

With 12 Expedia vacation rentals, you're sure to find just the right place for your Leesburg stay.

What’s there to see and do in Leesburg?

Tippecanoe Lake and Big Barbee Lake are a couple of lovely local spots to get outside and enjoy nature. While here, Stanton Lake and Oppenheim Woods are other places worth a visit.

What’s a vacation rental in Leesburg like?

Vacation rentals are private properties you can stay in for a long or short time in Leesburg. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.