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, 364 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, 907 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
The exterior view shows a charming tiny house with blue siding and a welcoming entrance. Flower beds with various plants frame the path leading to the door, while sunlight illuminates the surroundings and the nearby lake reflects the clear blue sky.
Tiny home in Howe
4.94 out of 5 average rating, 102 reviews

The Cozy Cottage by the Lake

This sweet, unique, tiny house is located on Pigeon Lake, just 15 minutes from Shipshewana and the heart of Amish country, and 55 minutes from Notre Dame! It is beautiful in any season, and offers a quiet retreat for families or friends. Guests have lake access, and the public boat launch nearby. Paddle boat, kayaking, and fishing from the pier at the house are all available from this property. (Fishing gear not provided) After a day in Shipshewana, relax in the outdoor porch and fire pit area!

Guest favourite
Cabin in North Webster
4.89 out of 5 average rating, 261 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, 142 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 welcoming front porch features two rocking chairs positioned beside a small decorative table, adorned with bright pink flowers. Lush greenery is visible in nearby planters, while sunlit windows with green shutters complete the charming country setting.
Guest suite in Shipshewana
4.97 out of 5 average rating, 565 reviews

Picket Fence Farm Private Guest Retreat Suite

Stay in a 2nd story private suite in a modern farmhouse where we reside on a family farm in Amish country. Guests have the entire 2nd floor: 2 bedrooms, a private bath, and a sitting room. You can watch Amish buggies drive by while you rock on the front porch, access shared patio spaces or sit by a creek. We have cows, goats & chickens. We're in the heart of Shipshewana Amish/Mennonite community, minutes from downtown Shipshewana & all it has. An authentic, comfortable country getaway.

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, 141 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!

Guest favourite
A fire pit surrounded by several chairs is set on a grassy area, providing a cozy gathering spot. A lake view is visible in the background, with docks and boats. A vibrant sunset sky adds color, while a kayak is propped against a tree nearby.
Home in Warsaw
4.88 out of 5 average rating, 24 reviews

Little Barbee Lakefront Bungalow

Step into a simpler time at our cozy, lakefront cottage on Little Barbee, where time slows down and relaxation takes over. Whether escaping with family or friends, immerse yourself in the joys of lakeside living. Engage in outdoor games, sizzle up a feast on the grill, and drink in the gorgeous waterfront views and spectacular sunsets. With your own private dock, there's space to moor your boat for aquatic adventures. Complete your perfect day with a crackling bonfire at the water's edge.

Top guest favourite
Cabin in Pierceton
4.94 out of 5 average rating, 107 reviews

Fishing · Kayaks · Firepit · Paddleboat

☀Ridinger Lakefront with private pier ☀Paddle boat and 2 kayaks/life jackets ☀Fishing paradise ☀Screened-in porch overlooking the lake ☀Private waterside gazebo ☀Firepit by the lake ☀Charcoal park-style grill steps from the house ☀Pet friendly ☀.3 mile walk to sandy Ridinger Lake beach/boat launch ☀1 king bedroom with comfy mattress, room darkening curtains ☀1 queen bedroom with comfortable mattress, room-darkening curtains ☀Pull-out couch/futon in the living room

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, 107 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 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, 401 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
A modern single-story house is shown with a spacious deck that features a gas grill and several comfortable seating areas. Large windows provide views of the interior, while steps lead from the deck down to a gravel area, emphasizing accessibility to the outdoor space.
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.

Popular amenities for Leesburg holiday rentals

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