Holiday houses in Leesburg

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Leesburg

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

%{current} / %{total}1 / 1
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, 354 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.
Apartment in Goshen
4.96 out of 5 average rating, 884 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 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, 251 reviews

Guesthouse Suites (C)

For business or pleasure, you will experience lovely Winona Lake staying in our newly constructed GuestHouse Suites. Next to the heart of The Village at Winona, a short walk up to Grace College or a short walk over to visit the shops and restaurants; Spring Fountain Park graces your view. Winona Lake Limitless Park, public beach, splash pad, tennis, pickleball and basketball courts, paved walking/bike trails, mountain bike trails, and an ice skating pavillion, are all within walking distance

Top Guest favourite
The exterior of a two-story home is presented, featuring a light brown facade with dark shutters. A well-manicured lawn surrounds the property, accented by neatly shaped shrubs. A covered porch with seating and decorative plants invites relaxation. Trees provide a natural backdrop.
Guest suite in Goshen
4.97 out of 5 average rating, 351 reviews

Lofty Spaces, entire upper level, 5 mi from town

Stay in our redecorated entire upstairs level with pass-coded private entry to come and go as you please. Queen bed in the primary bedroom, a double in the second bedroom. (2 cots can be set up for any youth). Full bath with tub and shower, TV room with Kuerig, microwave, mini frig, and back wood’s view. Relax on front porch. Short walk to Fairgrounds and Pumpkin Vine trail. Close by places to eat. Notre Dame is 45 mins away. Shipshewana -40 mins. 60 miles to Lake MI. 3 hr drive to Chicago.

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, 135 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, 345 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
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, 140 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 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, 190 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 cozy living room area features a comfortable sofa with decorative pillows and an ottoman. A small side table displays board games, while a lamp provides soft lighting. A door leads to the outside, complemented by a wall with colorful tiles.
Guest suite in Goshen
4.97 out of 5 average rating, 302 reviews

Colorful Country Suite

Peaceful get-away in the country. Rich colorful apartment ideal for an extended business trip or just for fun. A thousand square feet of comfortable living space in our walk-out basement. Five to ten minutes from an eclectic mix of dining options and bustling art/artisan scene in downtown Goshen. Walking/biking trails are 1.5 mi. away. Bike trails are also available in Goshen and extend all the way from Elkhart to Shipshewana. We're two minutes from Goshen Airport.

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.
Guesthouse in North Webster
4.98 out of 5 average rating, 251 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 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, 379 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.

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.
Apartment in Nappanee
4.97 out of 5 average rating, 200 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

  1. Airbnb
  2. United States
  3. Indiana
  4. Kosciusko County
  5. Leesburg