Holiday rentals in Leesburg

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Top-rated holiday rentals in Leesburg

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
An inviting porch features a spacious area with wooden beams supporting the roof. A blue swing hanging from the ceiling is complemented by comfortable seating arrangements and planters filled with greenery. The serene view of the lake is visible in the background.
Home in Syracuse
4.88 out of 5 average rating, 33 reviews

Dewart Lakefront Cottage

Escape to our charming Lake Cottage, nestled on the peaceful Dewart Lake in Syracuse, IN. Whether you're seeking a relaxing weekend or an adventurous getaway, this cozy retreat offers stunning lake views, beautiful sunrises and sunsets, private access on an all sport lake and all the comforts you need for a memorable stay anytime of the year. Enjoy the lake with kayaks, fishing from the pier and space for a boat, BBQ grill, smart TVs and campfire pit are just a few amenities we have to offer.

Guest favourite
Cabin in North Webster
4.89 out of 5 average rating, 270 reviews

Dock of Bay Cabin- Private Dock on Lake Webster

"Last Cast" 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 an eat in 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 w/ you or rent items @ 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
4.91 out of 5 average rating, 11 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!!

Guest favourite
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
5.0 out of 5 average rating, 31 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 favourite
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.
Flat in Warsaw
4.96 out of 5 average rating, 370 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.

Guest favourite
Cabin in Warsaw
4.97 out of 5 average rating, 152 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!

Top guest favourite
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
4.92 out of 5 average rating, 93 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 favourite
Guest house in Leesburg
4.96 out of 5 average rating, 23 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 favourite
A bright living area showcases a blend of comfortable seating and a dining table. Two large windows allow natural light to fill the space, which features a neutral color palette and hardwood floors. A television is positioned for entertainment, complemented by decorative accents.
Home in Leesburg
5.0 out of 5 average rating, 10 reviews

Cozy cottage on Irish Lake!

Come stay and play! This home offers everything you need to have a getaway at the lake. Wake up and enjoy a sunrise kayak ride around the lily pads watching the wildlife. Or sit on the deck with a cup of coffee. This adorable cottage with 1 bedroom, a sleeping loft and 1.5 baths lets you enjoy all the Barbee Chain has to offer. There are only a few steps off the deck to the private pier so bring your boat! There are convenient places to rent one if you don’t want to bring your own.

Guest favourite
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 favourite
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, 218 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.

Top guest favourite
A charming log cabin features a welcoming facade with large windows framed by wooden accents. The entrance is accessed via a stone pathway lined with landscaped garden beds, showcasing lush greenery and colorful plants. Surrounding trees provide a serene, natural setting.
Cabin in Middlebury
4.99 out of 5 average rating, 437 reviews

Cabin off 39 - Peaceful, private one bedroom cabin

Kick back and relax in this calm, stylish space. Nestled among the trees, it provides a quiet getaway from the chaos of life allowing you to recharge and renew. The main residence is approximately 400 feet from the cabin. The cabin is secluded and yet close to local attractions, restaurants, biking and nature trails. The Cabin has a total of 420 sq ft living space with 280 sq ft on the ground floor and a 140 sq ft bedroom loft.

Popular amenities for Leesburg holiday rentals

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