Leesburg Vacation Rentals

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Our top choices for Leesburg vacation rentals

10.0 out of 10, Exceptional, (22)
"Clean property, gewat location, loved the lake and the stars."
United States
joseph b.
$246 nightly
The price is $264
Dec 14 - Dec 15
Total with taxes and fees
Fishing · Kayaks · Firepit · Paddleboat
9.8 out of 10, Exceptional, (6)
"The cottage fits the description perfectly! It was probably the cleanest place I've ever stayed, which meant so much. It is as nice outside as in. Will definitely book again for a quiet weekend away."
United States
Ryan B.
$233 nightly
The price is $261
Dec 28 - Dec 29
Total with taxes and fees
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
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.
$269 nightly
The price is $301
Dec 14 - Dec 15
Total with taxes and fees
3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain

Vacation Home in Winona Lake

Trail Side in the Heart of Winona Lake
9.8 out of 10, Exceptional, (38)
"House very comfortable, we enjoyed being close to the trails"
United States
Dennis A.
$235 nightly
The price is $263
Dec 13 - Dec 14
Total with taxes and fees
Trail Side in the Heart of Winona Lake
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.
$278 nightly
The price is $311
Dec 21 - Dec 22
Total with taxes and fees
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

Vacation Home in Ligonier

Welcome to our Home in Ligonier
2.0 star property
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.
$217 nightly
The price is $243
Dec 12 - Dec 13
Total with taxes and fees
Welcome to our Home in Ligonier
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.
$258 nightly
The price is $278
Dec 12 - Dec 13
Total with taxes and fees
Heart Jacuzzi · Kayaks · Firepit · Pier
2.0 star property
9.8 out of 10, Exceptional, (16)
"We enjoyed our time away"
United States
lori b.
$268 nightly
The price is $272
Dec 15 - Dec 16
Total with taxes and fees
Lake House | Kayaks | Patio/Deck | Private Pier
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
$176 nightly
The price is $188
Dec 15 - Dec 16
Total with taxes and fees
Woodside Retreat in the Heart of Amish Country
10.0 out of 10, Exceptional, (120)
"This was an amazing place to stay. It was private and peaceful yet close to restaurants and shopping. The area is beautiful and we will definitely recommend this home to others. "
United States
Tina c.
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
9.6 out of 10, Exceptional, (16)
"Location was convenient for biking the the Pumpkin Vine Trail."
United States
Jon C.
$267 nightly
The price is $285
Dec 14 - Dec 15
Total with taxes and fees
Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!
10.0 out of 10, Exceptional, (10)
"Such a lovely place!It was spotless and peaceful"
United States
Marilee G.
$260 nightly
The price is $262
Dec 15 - Dec 16
Total with taxes and fees
Hidden Log Cabin | Hot Tub | Ping Pong | Family |
2.0 star property
10.0 out of 10, Exceptional, (6)
"It was a fantastic comfortable house to continue a long standing tradition if visitong Lake Wawasee. Nice being so close to the Frog Tavern."
United States
Mike H.
$221 nightly
The price is $248
Dec 14 - Dec 15
Total with taxes and fees
Lake Wawasee FROG House, Surround Sound & Bikes
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.
$326 nightly
The price is $365
Dec 12 - Dec 13
Total with taxes and fees
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Vacation Home in Bourbon

3-BR + Firepit, Coffee Bar & Grill
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.
$253 nightly
The price is $284
Dec 12 - Dec 13
Total with taxes and fees
3-BR + Firepit, Coffee Bar & Grill

Vacation Home in Wawaka

The Heron House @Waldron Lake
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.
$523 nightly
The price is $586
Dec 15 - Dec 16
Total with taxes and fees
The Heron House @Waldron Lake
$303 nightly
The price is $340
Dec 15 - Dec 16
Total with taxes and fees
Gram's Cottage on Lake Webster in North Webster, Indiana is the perfect getaway.

Vacation Home in Pierceton

Cozy lakefront home on Big Barbee Lake
10.0 out of 10, Exceptional, (12)
"we had a great time!"
United States
Tamara H.
$235 nightly
The price is $263
Dec 12 - Dec 13
Total with taxes and fees
Cozy lakefront home on Big Barbee Lake
10.0 out of 10, Exceptional, (16)
"Excellent lakehouse on lake Webster! Our family loved staying at this property and the owners take care of all the details. From water rafts, kayaks, air hockey, and Foosball, this is the house to choose for a large family stay, and I highly recommend it!"
United States
dpersky1
$631 nightly
The price is $677
Dec 14 - Dec 15
Total with taxes and fees
4BR Lakefront · Pier · Game Room · Sleeps 16+
10.0 out of 10, Exceptional, (2)
"Great views, spacious, clean home, responsive owner. "
United States
Bob T.
$470 nightly
The price is $526
Dec 14 - Dec 15
Total with taxes and fees
Private Lake Front Home on Wawasee - Exclusive and Quiet Ogden Island Retreat
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

Find out more about Leesburg

Everything you need to know about Leesburg vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Leesburg vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Leesburg vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Leesburg vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Leesburg. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Leesburg in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $285 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Leesburg rentals

At Expedia, we put the best Leesburg vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Leesburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Leesburg vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Leesburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!: Visitors like this Leesburg vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.