Leesburg vacation rentals

We found 147 vacation rentals — enter your dates for availability

Nestled amidst the tranquil beauty of lakes and lush parks, Leesburg invites travelers to indulge in outdoor adventures and charming neighborhoods filled with history and romance. Perfect for families and groups, this idyllic destination features a variety of vacation rentals, from cozy cottages to spacious homes, ensuring comfort and convenience for all. Explore nearby Warsaw and Syracuse for family-friendly activities, and return to your home-away-from-home to relax and unwind after a day of exploration.

Holiday rentals with weekly discounts - Leesburg

Showing deals for:Nov 6 - Nov 13

Image gallery for All-Sports Lakefront, Pier/Slip, Kayaks, 3Bd/2.5Ba, Sleeps 10

Living area
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

All-Sports Lakefront, Pier/Slip, Kayaks, 3Bd/2.5Ba, Sleeps 10

North Webster

8% off
Price is $303
$2,122 for 7 nights
All fees included
All-Sports Lakefront, Pier/Slip, Kayaks, 3Bd/2.5Ba, Sleeps 10

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Leesburg

Why visit Leesburg

  • Outdoor adventures: Leesburg is perfect for nature lovers, offering stunning lakes and inviting parks for various outdoor activities.
  • Charming neighborhoods: Explore friendly communities and romantic spots, ideal for couples and families alike.
  • Engaging history: Visit local museums that showcase the rich history and culture of the area.
  • Diverse accommodations: Choose from private homes, cozy cottages, and delightful cabins to suit any vacation style.
  • Nearby attractions: Enjoy family-friendly activities and relaxation in the surrounding cities of Warsaw and Winona Lake.

Popular types of accommodation in Leesburg

Discover the charm of Leesburg with our diverse vacation rental options, including houses, cozy cottages, and delightful cabins. Whether you're searching for a spacious family home or a convenient apartment lease, we have the perfect spot for you. Enjoy comfortable living rooms and all the amenities you need for a relaxing getaway. Explore our selection of Leesburg homes and find the ideal base for your next adventure.

  • Houses: The top choice for visitors in Leesburg, offering ample space and amenities for families and groups.
  • Cottages: A charming option for those seeking a cozy retreat, often nestled in scenic locations.
  • Cabins: Ideal for nature lovers, these rustic getaways provide a unique experience in the great outdoors.
  • Condos: A convenient choice that combines comfort and accessibility, perfect for short stays.
  • Apartments: A practical option for travelers, offering the comforts of home in various locations.**

Top attractions in and around Leesburg

Leesburg, Indiana, is the perfect destination for outdoor enthusiasts and those seeking a romantic getaway. With stunning lakes, inviting urban parks, and engaging history museums, there's something for everyone. Whether you're traveling with family or looking for a peaceful beach experience, the attractions in and around Leesburg promise memorable adventures in nature and culture.

  • Tippecanoe Lake: Experience the serene beauty of Tippecanoe Lake, perfect for outdoor activities and romantic getaways. Enjoy its sandy beaches and picturesque scenery, making it an ideal spot for relaxation and recreation.
  • Kosciusko Community Hospital: A vital medical center located 6 miles from Leesburg, Kosciusko Community Hospital emphasizes family care and community health, offering a welcoming environment for visitors and residents alike.
  • Lakeside Park: Just 9 miles away, Lakeside Park is an urban oasis featuring family-friendly amenities, walking trails, and green spaces, perfect for picnics and outdoor activities in a vibrant city setting.

Things to do recommended for couples

Experience the charm of Leesburg with a tranquil boat ride on Lake Tippecanoe, or enjoy a cozy dinner at a local bistro. Don’t miss a sunset stroll through the scenic parks, perfect for capturing those romantic moments together.

Things to do recommended for families

Families visiting Leesburg can enjoy a day at the nearby Lake Tippecanoe, perfect for swimming and picnicking. The local parks offer playgrounds and trails, while the Warsaw Community Public Library hosts engaging children's programs, making it an ideal spot for family fun and learning.

Things to do recommended for groups

Explore the scenic beauty of Lake Tippecanoe with a group fishing trip or enjoy a fun-filled day at the nearby Amish Acres, where you can experience farm tours, traditional meals, and unique shopping opportunities. Don't miss the local festivals for a taste of community culture.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Leesburg

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful tips for booking on Vrbo.

  • Traveling to Leesburg with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Leesburg with young kids: Traveling with young children can be quite challenging. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Leesburg: For many families, a vacation wouldn’t be the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly homes come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Leesburg: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Leesburg

Leesburg, Indiana, offers a delightful escape for those seeking outdoor adventures and serene scenery. Nearby attractions invite you to explore charming neighborhoods, friendly communities, and romantic spots perfect for couples. Venture into surrounding cities like Warsaw and Winona Lake for family-friendly activities and relaxation. Whether you prefer thrilling outdoor experiences or tranquil moments by the lake, your vacation in and around Leesburg promises unforgettable memories.

  • Warsaw: Located 7 miles from Leesburg, Warsaw is a charming city known for its outdoor experiences and beautiful scenery. Travelers flock here for its romantic ambiance and vibrant recreational areas. You can explore the local fairground, perfect for family-friendly fun, or enjoy the serene landscapes at nearby lakes and the national state park. The stunning dunes add to the area’s natural beauty, making it an ideal spot for a day of exploration and relaxation.
  • Syracuse: Situated 8 miles away from Leesburg, Syracuse offers a delightful mix of outdoor activities and picturesque views. This city is a haven for golf enthusiasts, featuring excellent golf courses alongside beautiful recreational areas. The nearby lakes and national state park provide ample opportunities for hiking and water activities, making it a perfect destination for those seeking both adventure and romance in a tranquil setting.
  • Milford: Just 5 miles from Leesburg, Milford is a quaint city where nature and outdoor recreation take center stage. Visitors come here for its scenic parks and engaging educational opportunities. The local golf course is a favorite among visitors, and the proximity to lakes and national state parks makes Milford an excellent choice for hiking and picnicking. With its charming atmosphere, it’s a wonderful place to unwind and enjoy the beauty of the surrounding landscape.

Best time to go to Leesburg

If you're planning a trip to Leesburg, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.2°F (-3.8°C)Light RainMostly CloudyAverageSlightly Low
February27.5°F (-2.5°C)Light RainMostly CloudyAverageSlightly Low
March38.8°F (3.8°C)Light RainMostly CloudySlightly HighSlightly Low
April48.7°F (9.3°C)Light RainMostly CloudyAverageAverage
May60.8°F (16.0°C)Light RainMostly SunnyAverageAverage
June69.4°F (20.8°C)Light RainMostly SunnySlightly HighAverage
July72.5°F (22.5°C)Light RainMostly SunnySlightly HighSlightly High
August70.9°F (21.6°C)Light RainMostly SunnyAverageAverage
September64.9°F (18.3°C)Light RainMostly SunnyAverageSlightly High
October53.4°F (11.9°C)Light RainMostly SunnySlightly LowSlightly High
November40.8°F (4.9°C)Light RainMostly SunnySlightly LowAverage
December31.8°F (-0.1°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, booking an extended stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the best options for your trip.

Vrbo Trips: Planning as easy as it gets

Vrbo's user-friendly Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or review and manage your travel arrangements. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Leesburg getaway

Experience the unique character of Leesburg with a stay in a vacation home rental. This city has something for everyone. If you're looking for accommodations with space to entertain friends and family, Vrbo 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 things to do in the city? Venture out of your vacation home and experience everything that Leesburg has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Wawasee Golf Club (9.9 mi / 16 km)
  • McCormick Creek Golf Course (11.1 mi / 17.8 km)
  • South Shore Golf Club (8.6 mi / 13.9 km)
  • Maxwelton Golf Club (9.4 mi / 15.1 km)
  • New Paris Speedway (11.9 mi / 19.2 km)
  • Wine Cellar Supply Winery (17.6 mi / 28.3 km)

Exploring the natural landscape of Leesburg

Whether you're an active traveler or just want to spend some time taking in the scenery, Leesburg is a great place to get out in nature. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • 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)

Traveling to and around Leesburg

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

Frequently asked questions

How much does it cost to rent a vacation home in Leesburg?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Leesburg to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Leesburg vacation house rentals?
You can find great discounts on house rentals in Leesburg on Vrbo, 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.
Where are the best areas for renting a beach house in Leesburg?
For renting a beach house in Leesburg, Indiana, travelers can explore the shoreline of Lake Tippecanoe, a popular spot for water activities and relaxation. The area around the public beach offers vacation rentals that provide convenient access to sandy shores, ideal for swimming, fishing, and boating. Many properties in this vicinity feature amenities such as outdoor decks, fire pits, and spacious yards, great for family gatherings and evening barbecues.

In addition, the nearby Barbee Lakes area is another excellent option for beach house rentals. Here, you'll find homes that often come with private docks, making it easy for guests to launch boats or enjoy water sports. Some properties may also include amenities like screened porches, game rooms, or even hot tubs, enhancing the overall vacation experience.

Additionally, the surrounding neighborhoods offer a tranquil lakeside atmosphere with opportunities for hiking and exploring nature. Rentals in this region typically provide comfortable living spaces, kitchens for self-catering, and easy access to local dining and shopping options.
What is the most popular type of vacation rental accomodation in Leesburg?
In Leesburg, vacation rentals primarily consist of cottages, vacation houses, and cabins, with several options available in this quaint area. These rentals often provide a rustic charm and a peaceful retreat, making them ideal for travelers seeking a relaxing getaway. Most accommodations feature amenities such as cozy living spaces, fully equipped kitchens, and outdoor areas for barbecuing or enjoying the natural surroundings. Many of these properties are situated near local lakes and parks, offering opportunities for fishing, hiking, and enjoying the outdoors.
Are there any family house rentals in Leesburg?
In Leesburg, Indiana, there are 12 family-friendly vacation rentals available for those looking to enjoy a getaway. The area offers a variety of homes that cater to families, featuring spacious living areas, full kitchens for preparing meals together, and outdoor spaces where children can play and explore. Many of these properties include amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for everyone.

Visitors can take advantage of nearby attractions, including beautiful lakes and parks that provide opportunities for fishing, hiking, and picnicking.
Can I find long-stay vacation rentals in Leesburg?
A long-stay vacation rental in Leesburg is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any remote work vacation rentals in Leesburg?
In Leesburg, Indiana, there are several remote work vacation rentals available, with around 16 options to choose from. Travelers can expect properties equipped with essential amenities for remote work, including high-speed internet provided by a third-party service, as well as dedicated desk spaces in rooms. Many rentals also offer complimentary Wi-Fi in public areas and in-room, ensuring connectivity throughout your stay.

The serene surroundings of Leesburg provide a peaceful backdrop for working remotely, with opportunities to explore nearby lakes and outdoor activities during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Leesburg vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Leesburg with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
What are popular rental amenities in Leesburg?
In Leesburg, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals conveniently. Many rentals also feature outdoor spaces such as decks or patios, great for enjoying the serene surroundings. Onsite parking is another common amenity, providing easy access for guests with vehicles. Additionally, some properties come equipped with modern conveniences like blenders, suiting those who enjoy making smoothies or other blended drinks during their stay.
When is the best time to visit Leesburg for a vacation rental?
The peak travel season in Leesburg occurs during the summer months of June through August, with July being the most popular time to visit. This vibrant period attracts families and outdoor enthusiasts looking to enjoy the warm weather and participate in various local activities, including fishing, boating, and exploring the beautiful lakes in the area.

During these summer months, temperatures typically range from the mid-70s to the low 80s Fahrenheit, providing comfortable conditions for outdoor excursions and sightseeing. Visitors can take advantage of the scenic trails and parks nearby, making it an ideal time for hiking or picnicking with friends and family.

For those seeking a more budget-friendly experience, consider planning your trip in October. This month offers a quieter atmosphere while still providing opportunities to appreciate the beautiful fall foliage and crisp autumn air. It's a great time to explore local attractions without the crowds, allowing for a more relaxed and immersive stay.

Ultimately, the best time to visit Leesburg for a vacation rental depends on whether you prefer the lively energy of the peak summer season or the serene charm of autumn.
How early should I book a Leesburg vacation rental?
Book your Leesburg vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Leesburg, Indiana, United States of America?
In Leesburg, Indiana, visitors can enjoy a variety of attractions that highlight the area's natural beauty and small-town charm. The nearby Lake Tippecanoe offers recreational activities such as fishing, boating, and swimming, making it a popular spot for outdoor enthusiasts. Vacation rentals in this area may provide easy access to the lake for a scenic getaway.

Additionally, the charming downtown area features local shops and eateries that reflect the community's character. Nearby parks, such as the Leesburg Town Park, provide green spaces for picnics and leisurely walks, enhancing the tranquil atmosphere of the town. For those interested in history, the area surrounding Leesburg includes several historical sites and museums that offer insight into the region's past.
Can I change or cancel my Leesburg home rental booking on Vrbo?
To find Leesburg vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Leesburg vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

More Vacation Ideas