Leesburg vacation rentals

We found 132 vacation rentals — enter your dates for availability

Discover a selection of 12 homes and other vacation rentals in Leesburg that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation rentals have the best amenities for spending time at your vacation home, which might include a fireplace and a washer and dryer. No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Leesburg

Showing deals for:Mar 27 - Apr 3

Image gallery for Lakefront Cottage on Big Barbee Lake with ALL the amenities to Enjoy the Lake!

Exterior
9.8 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)

Lakefront Cottage on Big Barbee Lake with ALL the amenities to Enjoy the Lake!

Leesburg

8% off
Price is $179
$1,256 for 7 nights
All fees included
Lakefront Cottage on Big Barbee Lake with ALL the amenities to Enjoy the Lake!

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Find out more about Leesburg

Why visit Leesburg

  • Outdoor Adventures: Enjoy scenic lakes and urban parks, perfect for hiking, fishing, and summer activities.
  • Charming Neighborhoods: Explore family-friendly areas with cozy homes and delightful vacation rentals.
  • Rich History: Discover historic sites and charming properties that reflect the town's heritage.
  • Romantic Getaways: Experience a romantic atmosphere ideal for couples looking to unwind together.
  • Variety of Accommodations: Choose from private homes, cottages, and cabins for a comfortable stay.

Popular types of accommodation in Leesburg

If you're looking for the perfect getaway in Leesburg, you'll find a variety of appealing vacation rentals to choose from. The most popular types of accommodations include houses, charming cottages, and cozy cabins. Whether you're searching for Airbnb options or spacious house rentals, Leesburg properties offer something for everyone. Enjoy your stay with transparency, savings, and peace of mind as you explore the beauty of this delightful town.

  • Houses: The top choice for travelers in Leesburg, offering spacious accommodations ideal for families or groups seeking a home-like atmosphere.
  • Cottages: A charming option for those looking to enjoy a cozy retreat, these quaint dwellings provide a unique and intimate experience.
  • Cabins: Perfect for nature lovers, these rustic hideaways immerse you in the beauty of the outdoors while providing comfort.
  • Apartments: A convenient choice for solo travelers or couples, these offer the essentials in a compact space.
  • Condos: Ideal for those wanting a blend of hotel amenities and home-like comfort, making them a popular pick for vacationers.**

Top attractions in and around Leesburg

Leesburg, Indiana, is perfect for outdoor lovers and those seeking a romantic getaway. Visitors can explore scenic lakes, urban parks, and the vibrant atmosphere of a modern college town. The area offers various attractions, including historic sites and family-friendly activities, making it an ideal destination for a diverse range of travelers. Be sure to check out the charming properties and rich history as you immerse yourself in all that Leesburg has to offer.

  • Tippecanoe Lake: Nestled in Leesburg, this stunning lake offers beautiful beaches and picturesque scenery, perfect for outdoor activities and romantic getaways.
  • Grace College: Located 7 miles from Leesburg, this modern college campus features vibrant city vibes and a dynamic atmosphere for students and visitors alike.
  • Lakeside Park: Just 9 miles away, this urban park is great for families, providing outdoor spaces and city vibes, ideal for picnics and leisurely strolls.

Things to do recommended for couples

For a romantic getaway in Leesburg, indulge in a delightful meal at Amish Acres, located 12 miles away. Enjoy the charming atmosphere that blends city vibes with a touch of romance, perfect for couples seeking a memorable dining experience together.

Things to do recommended for families

Families can explore the City-County Athletic Complex, a vibrant sports facility located 6 miles from Leesburg, perfect for sports enthusiasts. Enjoy various activities and soak up the lively atmosphere, making it an ideal spot for family fun and exercise.

Things to do recommended for groups

Experience the charm of Leesburg by catching a show at the Wagon Wheel Theatre, enjoying a round of golf at the South Shore Golf Club, or exploring the shops and attractions at Coppes Commons. These activities offer culture, sports, and family fun for everyone in your group.

*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 friends, family, pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Leesburg with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Leesburg with young kids: Traveling with young kids can be a bit tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private 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 trip isn't truly complete without their furry companions. If you can relate, take a look at Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that both you and your pets feel comfortable and at home.
  • Planning for a long term stay visiting Leesburg: If you're searching for vacation rentals that offer special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Leesburg

Leesburg, Indiana, offers a charming blend of outdoor adventures and romantic getaways. Explore the scenic beauty of nearby lakes and parks, perfect for summer activities. With family-friendly neighborhoods and a welcoming atmosphere, you can find delightful vacation rentals and cozy homes for a relaxing escape. Whether you're seeking adventure or tranquility, Leesburg provides an ideal backdrop for an unforgettable vacation experience.

  • Warsaw: Warsaw, located 7 miles from Leesburg, is a charming city known for its stunning outdoor scenery and recreational opportunities. Visitors can explore the local fairgrounds and educational venues, making it a great spot for families and couples alike. The nearby lakes and national parks offer beautiful landscapes perfect for hiking, fishing, and picnicking. Warsaw's vibrant community events and serene parks make it an ideal destination for those seeking a romantic getaway or a day of outdoor fun.
  • Syracuse: Just 8 miles away from Leesburg, Syracuse is a picturesque city that invites outdoor enthusiasts to explore its scenic beauty. Known for its recreational areas and well-maintained golf courses, Syracuse is perfect for a leisurely day of golfing or enjoying a relaxing afternoon by the lake. The nearby national state parks and dunes provide additional opportunities for hiking and nature exploration. Travelers will appreciate the charming atmosphere and the community's dedication to preserving its natural surroundings.
  • Winona Lake: Winona Lake, located 7 miles from Leesburg, is a beautiful destination for those seeking outdoor adventures and scenic views. This city boasts a variety of recreational areas, educational institutions, and campgrounds, making it an excellent choice for families and nature lovers. Visitors can enjoy the stunning lakefront, explore the national parks in the vicinity, and take advantage of the local college's cultural events. With its inviting atmosphere, Winona Lake is perfect for a romantic escape or a peaceful retreat in nature.

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 a breeze

Are you hoping to save on your upcoming travel plans? Being flexible with your travel dates can help, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. It's rewarding to be the organizer. When you join our travel rewards program, One Key, you can immediately access member discounts and earn as well as redeem OneKeyCash on eligible reservations. Sign up today and begin saving.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new getaways, manage your travel arrangements, or take a closer look at your bookings. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about 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:

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

  • Lake Waubee (4.2 mi / 6.8 km)
  • 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)

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

What is the best area to stay in Leesburg when booking a vacation rental?
When considering a vacation rental in Leesburg, Indiana, the area surrounding the charming downtown is an excellent choice. This neighborhood offers a delightful blend of local character, accessibility to amenities, and proximity to key attractions. Staying in this area places you near the picturesque Lake Tippecanoe, which is popular for fishing, boating, and enjoying scenic lakeside views. Additionally, the historic sites in and around the downtown area provide a glimpse into the region's rich history, making it a fascinating spot for exploration.

Another appealing option is the area close to the scenic wetlands and parks, where you'll find plenty of opportunities for outdoor activities like hiking and birdwatching. These properties tend to be surrounded by nature, offering a peaceful retreat while still being just a short drive from local dining and shopping options. Overall, the downtown and nearby nature-focused neighborhoods host a variety of vacation rental properties, ensuring visitors can find accommodations that suit their preferences and needs.
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 should focus on the picturesque locations around Lake Tippecanoe, which is known for its serene waters and recreational opportunities. The area near the public beach offers various vacation rentals that provide direct access to the lake, ideal for swimming, fishing, and boating. Many properties in this vicinity feature amenities such as spacious decks, outdoor grills, and fire pits, great for enjoying summer evenings by the water.

Additionally, the nearby Barbee Lake area presents more options for beach house rentals, with homes often boasting private docks and sandy shorelines, making them great for families looking to enjoy water activities and lakeside relaxation. Many rentals here come equipped with modern kitchens, comfortable living spaces, and sometimes even game rooms, enhancing the overall vacation experience.

For those who enjoy nature, the surrounding areas provide opportunities for hiking and exploring local parks, while the charming downtown Leesburg and nearby Winona Lake offer dining and shopping options, adding to the convenience for travelers.
What is the most popular type of vacation rental accomodation in Leesburg?
In Leesburg, vacation houses are the most popular type of rental, with about 11 available throughout the area. These properties typically offer spacious interiors with multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them suitable for families or larger groups. Additionally, several cottages and cabins can be found, providing a more rustic experience for travelers looking to connect with nature. These accommodations often feature outdoor spaces, such as decks or patios, great for relaxing after a day of exploring the nearby lakes and recreational areas.
Are there any family house rentals in Leesburg?
In Leesburg, Indiana, families will find a selection of approximately 13 vacation homes that cater to their needs. The area is known for its serene lakes and outdoor recreational activities, making it a great spot for family getaways. Many of these properties offer spacious living areas, fully equipped kitchens for easy meal preparation, and outdoor spaces where children can enjoy themselves.

The nearby Chain O' Lakes State Park presents opportunities for hiking, fishing, and boating, adding to the appeal for active families. Additionally, some rentals feature amenities such as private docks, fire pits for evening gatherings, and game rooms for indoor entertainment.
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 pet-friendly house rentals in Leesburg?
In Leesburg, Indiana, there are several pet-friendly house rentals available, making it a great choice for travelers who want to bring their furry friends along. Many of these properties offer amenities such as spacious yards, fully equipped kitchens, and cozy living areas, ensuring a comfortable stay for both pets and their owners. The surrounding area is serene, providing a tranquil environment superb for outdoor activities with pets. Nearby, you'll find scenic spots like the shores of Lake Tippecanoe, where guests can enjoy walking paths and open spaces.
Are there any remote work vacation rentals in Leesburg?
In Leesburg, Indiana, there are a variety of remote work vacation rentals available, with around 16 options to choose from. This charming town offers a peaceful environment ideal for remote work, with properties featuring essential amenities such as high-speed Wi-Fi, dedicated workspace with desks, and comfortable desk chairs. Many rentals may also include additional conveniences like computer monitors and quiet settings, allowing for productive workdays amidst the tranquility of the area.

The scenic surroundings of Leesburg, near lakes and parks, provide excellent opportunities for relaxation after work hours. Whether you prefer cozy cabins or spacious homes, you can find accommodations that cater to both your remote work needs and your desire for a serene getaway. 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 rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals, and WiFi for staying connected during their stay. Many properties also feature outdoor spaces such as patios or decks, providing a superb setting for relaxation or gatherings. Some rentals even come with a blender, suiting those looking to make smoothies or other blended beverages.
When is the best time to visit Leesburg for a vacation rental?
The best time to book a vacation rental in Leesburg is during the summer months of June to August, with July being particularly popular among travelers. This vibrant season attracts families and outdoor enthusiasts who flock to the area for its numerous lakes and recreational activities. The warm weather, with temperatures typically ranging from the mid-70s to the low 80s Fahrenheit, creates ideal conditions for swimming, fishing, and boating.

During these peak months, the community comes alive with local festivals and events, making it a lively time to explore the charming town and its surroundings. You can enjoy leisurely afternoons at nearby lakes or take part in various outdoor activities that showcase the natural beauty of Indiana.

If you're looking for a more budget-friendly time to visit, consider October. This month offers a quieter atmosphere and the chance to appreciate the stunning fall foliage that blankets the landscape. It's a great time for scenic walks and photography, with fewer crowds to contend with.

Ultimately, the best time to visit Leesburg hinges on whether you prefer the bustling energy of summer activities or the peaceful 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?
In Leesburg, Indiana, visitors can enjoy a variety of attractions that showcase the charm of this small town. The nearby Lake Tippecanoe is a popular spot for outdoor activities such as fishing, boating, and swimming, making it a great destination for those who appreciate nature. The area offers vacation rentals that provide easy access to the lake, ideal for families and groups looking to enjoy water-based recreation.

Additionally, the town's historic downtown features quaint shops and local eateries, allowing travelers to experience the local culture and cuisine. The nearby Tippecanoe River is also a lovely location for kayaking and canoeing, adding to the outdoor adventure options available. For those interested in local history, the area around Leesburg has several historical sites and museums that provide 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.

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