Holiday houses in Leesburg

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Top-rated holiday rentals in Leesburg

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Guest favourite
Cabin in North Webster
4.89 out of 5 average rating, 265 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.

Top Guest favourite
A spacious living area features a comfortable sectional sofa adorned with various textured pillows. A glass coffee table sits on a soft area rug, while natural light illuminates the space through large windows. Shelves with decor elements and a cozy seating area complete the inviting atmosphere.
Home in Silver Lake
4.98 out of 5 average rating, 151 reviews

Peaceful lake house

Take a break and unwind at this peaceful oasis where you will see Bold Eagles hanging out in our backyard tree. Enjoy kayaking and fishing during the day and beautiful sunsets in the evening. For the boating and fishing enthusiast, local boat launch just around the corner. Warsaw is 20 minutes away, where you can enjoy shopping, dining and sightseeing. For anyone seeking a larger city, Fort Wayne is a 45 minutes' drive, where you can visit the Zoo, Theatres and Botanical Conservatory.

Top Guest favourite
A comfortable living area features a large sectional sofa and a cozy bean bag chair, with light streaming through two windows. A coffee table sits at the center, and a fireplace adds warmth. A desk with a chair is positioned in one corner, while a ceiling fan circulates air.
Cottage in Warsaw
4.98 out of 5 average rating, 143 reviews

The Channel House @ Hoffman Lake

2 bedroom 2 bathroom cottage that is located on Hoffman Lake Channel. The Channel House is great for fishing right out of the back door. Conveniently located a drive from Warsaw, IN and several smaller towns. Bring nothing to this fully furnished cottage except your clothes and plan for fun. On site drive way parking, laundry, garage with pool table, darts, & air hockey. Several activities inside and out. Fire pit, outdoor seating and lounge chairs. We live nearby & can assist your stay!

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.
Apartment in Warsaw
4.96 out of 5 average rating, 362 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
4.96 out of 5 average rating, 137 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 well-lit bedroom features two spacious beds dressed in white linens. Two bedside lamps with blue bases provide soft lighting, while framed artwork adorns the walls. A mirror reflects the tranquil setting, and a small table offers a cozy touch.
Guesthouse in Winona Lake
5 out of 5 average rating, 264 reviews

Guesthouse Suite (C)

Experience the rich history of lovely Winona Lake when you book your stay in our GuestHouse Suites. Next to the heart of the Village At Winona, just steps up to Grace College or a short walk to visit the shops and restaurants. Enjoy a relaxing afternoon on the patio with the views of Spring Fountain park. WL Limitless Park and public beach, splash pad, tennis, pickleball and basketball courts, paved walking/bike trails, challenging mountain bike trails, are all within walking distance !

Top Guest favourite
The exterior view of the home is displayed alongside a serene lake. The structure features a blend of outdoor decks with seating areas, large windows, and a well-maintained yard with trees offering shade, all set against a clear blue sky.
Home in Warsaw
4.97 out of 5 average rating, 125 reviews

Relax 15 guests can enjoy Holidays & Everyday

Beautiful home in a quiet neighborhood on Barbee Chain of 7 Lakes ,Irish Lake Channel.Can be used for reunion corporate event birthday, bachelor bachelorette parties,fire pit Corn hole boards along with a fully stocked kitchen. Oklahoma Joe’s Gas &charcoal grill with a smoker box, 4 bedrooms 2 bath fenced in back yard for pets &kids.Pet fees apply. Parking for trailers trucks 2 Beautiful decks with gorgeous sunsets.Nice beach close by.Pontoons available to rent separately at the home.

Top Guest favourite
A modern kitchen area is highlighted by a large central island with a white countertop. Exposed brick walls add character, while vintage signage provides a nostalgic touch. A cozy seating arrangement features a small chair and a fireplace TV setup against the wall.
Guest suite in Middlebury
5 out of 5 average rating, 126 reviews

Mullet's Speed Shop

Refresh and relax at this newly constructed guest suite! Mullet's Speed Shop is conveniently located just 3 minutes from the famous Das Dutchman Essenhaus Restaurant and Bakery, less than 10 miles from the quaint shops of Shipshewana, and an easy 40 minute drive to Notre Dame (for the football fans). Take a bike ride or a peaceful walk on the Pumpkinvine Nature Trail less than 2 miles away. Nestled in the heart of Amish country, enjoy the buggies passing by!

Top Guest favourite
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, 270 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

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, 417 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.

Guest favourite
Cottage in Leesburg
4.94 out of 5 average rating, 17 reviews

Lakeside, Kayaks, Large Deck, Endless Water Views

Kick back and relax in this calm, stylish space centrally located on the Barbee Chain of Lakes. Enjoy a cup of coffee on the 465 square foot deck overlooking the lake and wildlife surrounding the property. If relaxing isn't your cup of tea, enjoy kayaking or paddle boating with equipment that is provided. There is 190 ft of water frontage with great fishing opportunities and plenty space is available for boat parking.

Guest favourite
A charming exterior view of a single-story home surrounded by greenery, featuring a large front porch with white railings and steps leading up to it. Flower pots are displayed near the entrance, enhancing the inviting appearance of the home.
Home in Winona Lake
4.89 out of 5 average rating, 175 reviews

Mineral Springs Hideaway

The Mineral Springs hideaway is a perfect peaceful getaway. Located two blocks from the beautiful Lake Winona and the The village of Winona a vibrant destination steeped in history. If you love to hike and bike the greenway is less than a block away. Grace College is a three minute walk. We know you’ll love experiencing a peaceful hideaway in northern Indiana.

Popular amenities for Leesburg holiday rentals

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  4. Kosciusko County
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