Leesburg holiday rentals

We found 150 holiday rentals — enter your dates for availability
Select from 13 homes, 11 cottages and other holiday rentals in Leesburg to find one that's perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for spending time at your holiday home, including air conditioning and cable TV. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Leesburg

Showing deals for:25 Dec - 1 Jan

Outdoor dining
Interior
Interior
Private kitchen
Exceptional
(16 reviews)

The Chateaux on Winona Lake

Warsaw

12% off
AU$4,175
for 7 nights, 1 home
AU$596 per night
includes taxes & fees
The Chateaux on Winona Lake
Interior
Marina
Exterior
Exterior
Exceptional
(26 reviews)

Cozy three-bedroom cottage perfect for a lakeside get-away

North Webster

8% off
AU$1,728
for 7 nights, 1 cottage
AU$247 per night
includes taxes & fees
Cozy three-bedroom cottage perfect for a lakeside get-away
Exterior
Outdoor spa tub
Interior
Living area
Wonderful
(10 reviews)

Lake Days & Family Nights | Webster Lake Retreat

North Webster

8% off
AU$3,193
for 7 nights, 1 home
AU$456 per night
includes taxes & fees
Lake Days & Family Nights | Webster Lake Retreat
Property grounds
Outdoor dining
Interior
Interior
Wonderful
(9 reviews)

Steps From Grace Campus and Overlooks the Winona Lake Village

Winona Lake

11% off
AU$2,190
for 7 nights, 1 home
AU$313 per night
includes taxes & fees
Steps From Grace Campus and Overlooks the Winona Lake Village
Panoramic view of the living area excluding the bedrooms and the bathrooms.
View from the lower deck of Owner's house, limited use of Tiki Bar considered.
Marina
Exterior
Exceptional
(31 reviews)

Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,

Syracuse

8% off
AU$2,615
for 7 nights, 1 apartment
AU$374 per night
includes taxes & fees
Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,
Outdoor dining
Living area
Private kitchen
Exterior
Exceptional
(28 reviews)

Winona Lake Access With Pier

Warsaw

11% off
AU$1,728
for 7 nights, 1 home
AU$247 per night
includes taxes & fees
Winona Lake Access With Pier
Living area
Terrace/patio
Dining
Room
Exceptional
(77 reviews)

Sunset View, 2 Story Lake Home, 4br, 2bth, Sleeps 12 Comfortably

North Webster

8% off
AU$3,167
for 7 nights, 1 home
AU$452 per night
includes taxes & fees
Sunset View, 2 Story Lake Home, 4br, 2bth, Sleeps 12 Comfortably
Private kitchen
Exterior
Private kitchen
Room
Exceptional
(42 reviews)

The Winona Lake Chalet 2

Winona Lake

11% off
AU$2,195
for 7 nights, 1 home
AU$314 per night
includes taxes & fees
The Winona Lake Chalet 2
Room
Dining
Private kitchen
Interior
Exceptional
(13 reviews)

Lake and marina 5 minutes away Large family friendly Cozy home with country feel

Warsaw

8% off
AU$3,300
for 7 nights, 1 home
AU$471 per night
includes taxes & fees
Lake and marina 5 minutes away Large family friendly Cozy home with country feel
Room
Living area
Property grounds
Living area
Exceptional
(26 reviews)

Downtown loft apartment with rooftop balcony

Warsaw

6% off
AU$1,957
for 7 nights, 1 apartment
AU$280 per night
includes taxes & fees
Downtown loft apartment with rooftop balcony
Interior
Interior
Living area
Living area
Exceptional
(27 reviews)

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

Leesburg

8% off
AU$3,214
for 7 nights, 1 home
AU$459 per night
includes taxes & fees
“Stay Anchored” Lake Tippecanoe channel front with pier and great lake views
View from the back by the Channel
Another overview of entire property.
Overview of the entire property including Owner's home and Tiki Bar
Newly renovated Kitchen for 2022.
Excellent
(36 reviews)

Lake Wawasee 2 Bedroom Condo on Channel . NO SHOES, NO SHIRT, NO PROBLEMS !!!

Syracuse

14% off
AU$1,809
for 7 nights, 1 apartment
AU$258 per night
includes taxes & fees
Lake Wawasee 2 Bedroom Condo on Channel . NO SHOES, NO SHIRT, NO PROBLEMS !!!
Garbage disposal and lots of cooking preparation room.
View from Back Porch Restaurant where we boat in on Lake Wawasee.
Master bedroom with California King bed.
Viewing of dining room and living room. Large windows look out to water.
Exceptional
(10 reviews)

Unique 3 BR, 2 BR Waterfront Home/Vacation Getaway in Syracuse, Indiana

Syracuse

16% off
AU$3,361
for 7 nights, 1 home
AU$480 per night
includes taxes & fees
Unique 3 BR, 2 BR Waterfront Home/Vacation Getaway in Syracuse, Indiana

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Leesburg getaway

Learn about the unique charm of Leesburg with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Leesburg

Are you looking for attractions to see during your stay? Venture out of your holiday home and experience everything that makes Leesburg a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • South Shore Golf Club (8.6 mi / 13.9 km)
  • Wawasee Golf Club (9.9 mi / 16 km)
  • McCormick Creek Golf Course (11.1 mi / 17.8 km)
  • Maxwelton Golf Club (9.4 mi / 15.1 km)
  • New Paris Speedway (11.9 mi / 19.2 km)

Exploring the natural landscape of Leesburg

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Leesburg is a great place to get out in nature. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Big Chapman Lake (4.5 mi / 7.2 km)
  • Hidden Lake (4.6 mi / 7.4 km)
  • Tippecanoe Lake (4.7 mi / 7.5 km)
  • Dewart Lake (4.8 mi / 7.8 km)
  • Pike Lake (5.5 mi / 8.8 km)
  • Winona Lake (7.4 mi / 12 km)

Travelling to and around Leesburg

The nearest airport is in Goshen, IN (GSH-Goshen Municipal), located 13.6 mi (21.9 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into South Bend, IN (SBN-South Bend Intl.), which is 35 mi (56.3 km) away.

Frequently asked questions

What is the best area to stay in Leesburg when booking a holiday rental?
When considering a holiday rental in Leesburg, Indiana, the area around the charming community itself offers a delightful mix of tranquillity and local attractions. The neighbourhoods near the centre provide easy access to the serene beauty of the surrounding lakes, making it an ideal spot for those who appreciate nature. One of the primary draws in this region is the picturesque Lake Tippecanoe, which not only offers stunning views but also opportunities for boating, fishing, and picnicking, great for families or couples seeking a relaxing getaway.Moreover, the nearby town of Warsaw, just a short drive away, features attractions like the iconic Kosciusko County Historical Society and the lovely Central Park, which is great for leisurely walks or enjoying outdoor events. Staying in Leesburg allows you to enjoy a peaceful retreat while still being close to these vibrant local experiences.
Where are the best areas for renting a beach house in Leesburg?
For renting a beach house in Leesburg, Indiana, you'll want to focus on the nearby areas surrounding Lake Tippecanoe, which is a popular spot for water-based activities and relaxation. The lakeside properties here often feature amenities such as private docks, outdoor fire pits, and spacious decks for enjoying the stunning views of the water. Many holiday rentals come fully equipped with kitchens, allowing guests to prepare meals and dine al fresco while taking in the serene surroundings.Additionally, the nearby areas of Oakwood and the Tippecanoe Lake area offer charming cottages and larger family homes, great for groups looking to spend time by the water. These rentals typically include access to community amenities like swimming beaches, picnic areas, and boat ramps, making it easy to enjoy a variety of recreational activities such as fishing, kayaking, and swimming.The region is also known for its natural beauty, with opportunities for hiking and exploring the tranquil landscapes of northern Indiana.
What is the most popular type of holiday rental accomodation in Leesburg?
In Leesburg, cottages are the most popular type of holiday rental, with about 18 available in the area. These charming properties often feature cosy interiors, fully equipped kitchens, and outdoor spaces that allow guests to enjoy the peaceful surroundings. Many cottages also come with amenities such as fireplaces and patios, great for relaxing after a day of exploring.Additionally, there are around 16 holiday houses that cater to larger groups or families, providing ample space with multiple bedrooms and living areas. These homes typically include modern conveniences and may also have outdoor facilities like decks or gardens. Furthermore, several cabins are scattered throughout the region, offering a rustic experience for those looking to immerse themselves in nature.
Are there any family house rentals in Leesburg?
In Leesburg, Indiana, families will find a selection of approximately twelve holiday rentals that cater to their needs. This charming area, known for its picturesque lakes and outdoor activities, offers homes with spacious living areas, fully equipped kitchens, and amenities like Wi-Fi and air conditioning to ensure a comfortable stay.Many of these properties are situated near popular attractions such as Lake Tippecanoe, which is great for swimming, fishing, and picnicking. Visitors can also explore nearby parks that feature playgrounds and walking trails, ideal for family outings.
Are there any remote work holiday rentals in Leesburg?
In Leesburg, Indiana, there are around 32 remote work holiday rentals available for travellers looking to combine work and leisure. This charming town offers a variety of properties that cater to remote workers, featuring essential amenities such as Wi-Fi, which is often complimentary in the accommodations. Many rentals provide dedicated workspaces, ensuring a comfortable environment for productivity.In addition to work-friendly features, these properties often include comfortable living areas, well-equipped kitchens for preparing meals, and outdoor spaces to relax after a busy day. The peaceful surroundings of Leesburg allow for a refreshing escape, with nearby lakes and parks offering opportunities for outdoor activities during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Leesburg?
In Leesburg, popular rental amenities include well-equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also feature outdoor spaces, such as decks or patios, superb for enjoying the pleasant surroundings. Onsite parking is commonly available, ensuring convenience for those travelling by car. Additionally, many rentals come with amenities like blenders, suiting those who enjoy making smoothies or other blended beverages during their stay.
When is the best time to visit Leesburg for a holiday rental?
The peak season in Leesburg falls between June and August, with July being particularly popular among travellers seeking a summer getaway. During this vibrant period, visitors can indulge in outdoor activities like fishing, boating, and hiking, all while enjoying warm temperatures that typically range from 20 to 30 degrees Celsius. The community buzzes with life, making it an ideal time for families and friends to create lasting memories.For those looking for a more tranquil experience, October presents an excellent time to visit Leesburg. This month showcases the stunning autumn foliage, creating a beautiful backdrop for leisurely walks and scenic drives. The weather is pleasantly mild, making it comfortable for outdoor exploration and enjoying the local parks without the summer crowds.
What are the top attractions in Leesburg?
In Leesburg, Indiana, visitors can explore several attractions that highlight the area's natural beauty and local charm. The picturesque Lake Tippecanoe is a significant draw, offering opportunities for fishing, boating, and swimming, making it ideal for outdoor enthusiasts. The nearby Tippecanoe Lake Country Club provides a lovely setting for golf lovers looking to enjoy a round of golf amidst scenic surroundings.For those interested in local history, the Leesburg Historical Museum features exhibits that showcase the area's heritage and culture, providing a glimpse into the past. The quaint downtown area features charming shops and local eateries, great for a leisurely afternoon stroll.Additionally, the surrounding Kosciusko County offers various parks and nature reserves, such as the nearby Winona Lake, where visitors can partake in hiking, biking, and enjoying the tranquil lakeside views.
Are all fees included in the Leesburg holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Leesburg holiday homes with parking?
Stayz offers a wide selection of holiday homes in Leesburg with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Leesburg holiday homes?
You can find great discounts on holiday homes in Leesburg on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Leesburg holiday home booking on Stayz?
To find Leesburg holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Leesburg?
A long-stay holiday home in Leesburg is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Leesburg holiday home?
Book your Leesburg holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Leesburg?
Prices for holiday homes in Leesburg vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Leesburg to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.