Vacation rentals in Leesburg

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Top-rated vacation rentals in Leesburg

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Guest favorite
A log cabin with a welcoming front porch is surrounded by lush greenery. A gravel driveway leads up to the cabin, which features large windows and a rustic design. Natural light filters through the trees, enhancing the serene outdoor setting.
Cabin in North Webster
4.89 out of 5 average rating, 215 reviews

Dock of the Bay Fishing Cabin with Boat Dock

"Livin Easy" is close to town, creating the perfect space to have access to peace & quiet while being close to town & water. This cabin is on a private property that guests will have all to themselves while they are here. You will have access to a full kitchen, living room, private bathroom, and a loft which has two beds. This cabin comes w/channel dock space on the S. side of Lake Webster. There is space for your boat & water toys to bring along with you or you to rent @ a marina while here.

Superhost
A firepit area is set on a green lawn, surrounded by four chairs arranged in a circle. In the background, the calm lake reflects the blue sky with fluffy white clouds, while a dock and a kayak can be seen along the shore.
Home in Leesburg
4.88 out of 5 average rating, 17 reviews

Lakehouse, kayaks, dock, fishing, fence for pets!

Beautiful lakefront home on the Barbee chain of lakes. Small, but all you need!! This guesthouse features a kitchen, family room, firepit, dock for your boat, and a fenced in side yard for your dogs!! We supply 2 kayaks with lifejackets and a grill. King size bed in the bedroom! We have a loft for the kids that they will love!!! This house has the best views and best fishing on the chain! Must be 21 to book and show ID after booking confirmation. Plenty of parking. Come make some memories!!

Top guest favorite
The outdoor lakeside area is illuminated with string lights, creating a calming ambience. The cottage features a spacious patio with several seating options. A white railing outlines the dock, which leads to the calm water, reflecting the soft light from the surroundings.
Home in Warsaw
5 out of 5 average rating, 36 reviews

Lakefront Paradise Cozy Cottage

Welcome to our recently renovated Lakefront Paradise Cozy Cottage! Escape to your very own retreat offering 50 feet of prime waterfront on Sechrist Lake (Barbee Chain). Step outside and find yourself right next to the waters, where you can relax on the lakeside patio and soak in the stunning views featuring a nice sandy bottom, perfect for swimming and water activities. Whether you're looking for a peaceful getaway or a lively retreat, this lake cottage is ideal for making lasting memories.

Top guest favorite
A cozy sleeping area features a plush queen bed, adorned with decorative pillows. Natural light streams through skylights, illuminating the space. A wooden dresser adds warmth, while a dreamcatcher hangs on the wall, complementing the tasteful decor and providing a relaxing atmosphere.
Apartment in Warsaw
4.97 out of 5 average rating, 372 reviews

The Loft: 1880

Located near, Zimmer-Biomet, and Cinema. Perfect for business travelers & those visiting family & friends. We've hosted contract workers & parents visiting Grace College students. The Loft is a second-story self-contained annex attached via a private entrance. On-Site Parking. We are situated on 3 acres and love our 1909 farmhouse and The Barn 1880: Historic Venue. Open plan living/dining w/fully equipped kitchen w/coffee bar, separate private queen bedroom & private bathroom. See Reviews.

Top guest favorite
Cabin in Warsaw
4.97 out of 5 average rating, 157 reviews

Romantic A-frame · HeartJacuzzi · Firepit · Kayaks

Peaceful channel-front A-frame cabin on Barbee Chain of 7 lakes! This cozy retreat features a charming, rustic interior, fully stocked kitchen, and heart-shaped jacuzzi. You'll love stargazing or drinking morning coffee on your spacious deck with gas firepit and gas grill. Unwind by the cozy fireplace, kayak and fish on the Barbee Chain of 7 lakes, and make s’mores by the waterside firepit! Minutes from boat launch. Book now for unforgettable memories in this intimate, picturesque getaway!

Superhost
A spacious living area features a large sectional sofa and a round coffee table. A flat-screen television is mounted above a modern fireplace. Natural light filters through large windows, highlighting the serene outdoor view of farmland. A potted plant adds a touch of greenery.
Home in Leesburg
4.94 out of 5 average rating, 17 reviews

Tippecanoe Lake-Family Friendly-4Bedroom

Have fun with the whole family at this stylish place. A newly renovated home that has a warm and comforting feel throughout. Country living that includes 4-bedrooms featuring 2 master bedrooms. The large kitchen is accommodating for all with brand new appliances, luxury vinyl flooring, quartz countertops and specialty bars. Cozy seating areas with a game corner, social media friendly area with beautiful natural lighting to capture the moment. Marina and public lake access minutes away.

Top guest favorite
A collage showcasing the lakefront view at sunset, highlighting calm waters and distant docks. An interior view features a well-lit living area with comfortable seating and a dining table, alongside cozy bedding and decorative accents, providing a sense of warmth and relaxation.
Cottage in Warsaw
4.93 out of 5 average rating, 96 reviews

Lake Haven Cottage • Fun Summer Get Away

We invite you to come enjoy your time away at our delightful summer lake front cottage on Little Barbee Lake. Close proximity to Big Barbee Lake (all sports lake) Little Barbee is part of the Barbee Chain of Lakes with plenty of room to boat and fish. Bring your own boat or jet ski as the dock is steps away from the cottage. ••• Sunday AND Holiday check-ins may be available depending on our cleaning schedule! Please contact me and we'll do our very best to accommodate your schedule!

Guest favorite
Guesthouse in Leesburg
4.96 out of 5 average rating, 24 reviews

Tippy Lake Retreat | Kayaks, Bonfires & Lake Views

UNIQUE, SPACIOUS, and HAS IT ALL! Views and Sunsets of Lake Tippecanoe - All Sports Lake; second to none! Space to sleep a minimum of 12, 2 full baths with private w/c, walk-in showers, a gas fireplace, amazing 1940's Century boat island, lake access and pier use just steps away, pier space for personal watercraft boat rentals available, please ask for promo code! Kayaks, paddle boards, reverse osmosis water, charcoal grill, outdoor seating, fire pit, artificial grass area, and more!

Guest favorite
A peaceful waterfront view features calm waters reflecting surrounding greenery. A wooden pier extends into the water, bordered by grassy areas. Various boats are visible in the distance, adding to the serene atmosphere of the lake access area.
Home in Warsaw
4.93 out of 5 average rating, 57 reviews

The Little Barbee Lodge *Lake Access*

Welcome to a cozy getaway, The Little Barbee Lodge. Our 2 bedroom, 1 bath cottage is located off the channel *lake access* of Little Barbee Lake! Equipped with the things you need for a relaxing vacation. Watch the sunrise on the screened-in patio. Enjoy the water and the land with our 2 kayak's & 2 adult bikes! In the evening, enjoy a bonfire. *The Barbee Chain of Lakes are noted for the fishing/hunting. I have pier space available for an additional charge. Bring your boat!

Top guest favorite
The exterior of the cottage showcases a modern design with a white façade and black accents. A small porch features wooden steps leading to the front door. A black bench with red flowers is positioned beside the entrance, with a well-maintained grassy area nearby.
Home in Winona Lake
4.96 out of 5 average rating, 222 reviews

Short Walk to the Lake and Trails

The 123 Cottage is perfect for a peaceful getaway. You will be staying in an ideal central location with the ability to explore the historical Winona Lake. In just a short walk, you can visit The Village with local shops/restaurants along the canal or The Limitless park with a public beach, playground, splash pad, volleyball courts, tennis courts, pickle ball courts, and basketball courts. Feeling a bit more adventurous? Take a scenic walk on the Greenway or ride the bike trails.

Guest favorite
Cabin in Nappanee
5 out of 5 average rating, 5 reviews

The Retreat at Cabin Creek Farms

Escape to our peaceful country cabin nestled down a quiet lane surrounded by rolling farmland and grazing cows. Enjoy spacious accommodations with a wrap-around patio perfect for morning coffee, cozy evenings by the indoor fireplace, and scenic hiking trails right at your doorstep. Your perfect rural getaway awaits! Small events for up to 30 people are allowed upon request before with an extra fee, if interested in hosting an event please request before making the reservation!

Top guest favorite
A sandy lakefront area is visible, featuring several brown Adirondack chairs arranged in a circle around a fire pit. In the background, a wooden dock leads to a covered boat lift, with calm waters reflecting the clouds above.
Cottage in Warsaw
4.96 out of 5 average rating, 272 reviews

Lakewood Cottage on Winona Lake

Modern and light filled lakefront cottage on beautiful Winona Lake. Great views from the lakefront dining area. You walk in the front door and you feel surrounded by the water. Quiet neighborhood is great for biking and walks. You can access the Greenway trail a mile away which takes you to the Village of Winona. Check out our custom video on youtube, just copy and paste the below code into the youtube search bar. AMErvK41MSo

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