Holiday rentals in Leesburg

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Top-rated holiday rentals in Leesburg

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Top guest favourite
An exterior view of the charming home showcases the covered front porch with wooden railing and welcoming entryway. A lantern hangs above the door, and flower beds with colorful blooms are visible along the side. A sign indicating 'NO SMOKING' is prominently displayed.
Home in Winona Lake
4.99 out of 5 average rating, 357 reviews

Off The Beaten Pass -on Greenway .3 mi Beach/Park

Charming home nestled on Greenway Trails in historic Winona Lake, IN. Completely renovated in 2017 with cozy living space. Walking/biking distance to Beach, Park, Playground, Splash Pad, Tennis Courts, Basketball Court, Volley Ball Court, The Village shopping & restaurants, Grace College. Beautiful sunsets from the beach! Perfect for couples, solo adventurers, business travelers, small families, mountain bike get-aways, cross-country skiing, weekend tailgating Notre Dame Football games, etc!

Top guest favourite
The spacious living area features arched ceilings and large windows, allowing natural light to fill the room. Comfortable seating is arranged around a central coffee table, with a flat-screen TV mounted on the wall. The adjacent kitchen includes stainless steel appliances and cabinetry.
Flat in Goshen
4.96 out of 5 average rating, 887 reviews

Half-Moon Cottage

Enjoy privacy in this beautifully handcrafted cottage with arched ceilings. The cottage is 2 miles from downtown Goshen - a vibrant small town with restaurants and shops. It's 1 mile from Goshen College, 45 minutes from Notre Dame and 25 minutes from the Amish town of Shipshewana. The cottage is beside a fruit, nut and berry orchard and gardens. It's adjacent to a city bike trail that links to the Pumpkinvine nature/bike trail. It's close to a train crossing (with whistle) and a busy street.

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, 128 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, 136 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.
Flat in Warsaw
4.96 out of 5 average rating, 349 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 favourite
A hand holds a light blue mug on a wooden table, with tea bags placed nearby. The serene lake reflects autumn colors from the surrounding trees, enhancing the peaceful waterfront view.
Cottage in Warsaw
4.97 out of 5 average rating, 144 reviews

Cozy Cottage

Take it easy at this unique and tranquil getaway. The lake is not a swimming lake, but views are spectacular. Enjoy the wildlife, swans, beaver, otter, the pair of bald eagles that reside on Palastine Lake. Enjoy the newly renovated inside space, centered around comfort and relaxation. A comfortable bed with soft sheets. Knead your worries behind on the heated massage chair. Enjoy a warm fire either outside on the deck or the inside wood burning fireplace. Rest and renew at Cozy Cottage.

Top guest favourite
The entrance to the A-frame cabin is framed by a distinctive stone facade, featuring a welcoming sign and neatly arranged potted plants. Grass surrounds the exterior, with shade provided by nearby trees, enhancing the inviting appearance of the entryway.
Cabin in Warsaw
4.96 out of 5 average rating, 106 reviews

Heart Jacuzzi · Kayaks · Firepit · Pier

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
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, 193 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 favourite
The image showcases a spacious kitchen area with a granite countertop extending into the dining space. A well-lit dining table is surrounded by wooden chairs, while a living area featuring a sectional sofa is visible in the background. Natural light streams through the windows, enhancing the open feel.
Guest house in North Webster
4.89 out of 5 average rating, 176 reviews

Come relax near beautiful Lake Webster

Our place is close to Webster Lake beach & boat ramps w/boat rentals. Whether you are looking for a relaxing getaway or to gather with friends & family you’ll love our place because of the location. We are centrally located between South Bend (Notre Dame) and Fort Wayne (Tincaps stadium/ Coliseum), close to many small towns w/ lakes, great eateries, & antique shops. With so much to offer you can find something to do for everyone or stay in & relax in our relaxed environment.

Top guest favourite
A comfortable sitting area features a gray sofa with an accompanying ottoman, situated beside two side tables with lamps. Natural light enters through the window, highlighting neutral-colored walls and plush carpeting, creating a relaxed environment for guests.
Home in Nappanee
4.99 out of 5 average rating, 100 reviews

Country Cottage

Located in the peaceful countryside of Nappanee, enjoy this charming house which is less than 3 miles to the nearest town with grocery store, restaurants, and shops. The front porch is a lovely place to unwind and relax, weather it's after a day of work or play or then to sip your morning coffee, with the occasional passing of a horse and buggy on this country road. There is No smoking in the house or on the property. No pets allowed.

Top guest favourite
A grey house with solar panels is seen alongside a driveway, featuring a parked white SUV. Lush orange flowers bloom prominently in the foreground, while multiple trees provide greenery in the background under a blue sky.
Guest house in North Webster
4.98 out of 5 average rating, 255 reviews

Modern Webster Lake cottage

This home has a great floor plan for 2-4 people with a small loft bed for a youngster. It has high end kitchen accessories and in-unit washer and dryer. Water softener for great water, maple hardwood floors and a front deck for outdoor barbecuing. Parking for 3 cars and a shed with lots of amenities including bikes and hammock for recreation and relaxing. New in 2024, new rug, blackout curtains and solar panels! EV charger free for guests!

Top guest favourite
A modern farmhouse exterior is showcased, featuring a white façade with stone accents and a grey metal roof. The front porch is adorned with comfortable seating and surrounded by landscaped gardens. A garage is visible on the left, enhancing the welcoming appearance of the property.
Flat in Nappanee
4.97 out of 5 average rating, 201 reviews

Nappanee Loft

Welcome to the Nappanee Loft, a modern farmhouse, above-garage apartment located in the historic town of Nappanee, Indiana. Inside, you'll find touches of Nappanee with a restored, vintage Coppes Nappanee kitchen and fresh Homemade Granola and milk in the fridge. We hope they'll help you feel the warmth of small town hospitality in the heart of Amish Country.

Popular amenities for Leesburg holiday rentals

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  2. United States
  3. Indiana
  4. Kosciusko County
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