Vacation rentals in Leesburg

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Top-rated vacation 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, 363 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!

Guest favourite
The heated in-ground pool features a diving board and a slide, surrounded by a spacious deck with lounge chairs and a shaded patio area. The inviting turquoise water reflects the clear sky, creating a relaxing outdoor space for leisure and enjoyment.
Home in Milford
4.98 out of 5 average rating, 102 reviews

Pool, Game Room, Hot Tub, lots of family fun!

From the heated in-ground pool, to the large hot tub, to the huge heated/a/c game room, you will love your stay at our Milford location. Created with comfort and fun in mind there is no end of things to do and places to unwind and enjoy the relaxation of a home away from home. With sizzling hot Wi-Fi, this place is perfect for a girl's weekend, a couples retreat, an extended stay with your family, or a work trip. All the details are well thought out to create a perfect getaway for every group.

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, 905 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.

Guest favourite
The exterior of a cabin is presented, showcasing a wooden structure with a metal roof. A spacious porch features a wooden railing and seating area, surrounded by snow-covered ground and tall trees, creating a serene winter atmosphere.
Cabin in North Webster
4.89 out of 5 average rating, 204 reviews

BayFishing Cabin with Boat Dock

"Livin Easy" 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 a full 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 with you or you to rent @ 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, 140 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, 561 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, 140 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, 355 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
Cabin in Warsaw
4.97 out of 5 average rating, 127 reviews

Couples A-frame · Heart Jacuzzi · 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!

Guest favourite
An open layout showcases the studio apartment's main living area, featuring a cozy seating chair and a spacious bed. Large windows allow natural light to illuminate the space, while a modern kitchen with a wood-topped counter and a gas stove is positioned prominently.
Apartment in North Webster
4.92 out of 5 average rating, 100 reviews

Clean and Cozy Studio Apartment

Looking for a clean, comfortable place to rest while visiting town? This cozy garage studio apartment is the perfect getaway for the couple wanting to enjoy our small lake community or a quick overnight while passing through. Completely renovated with a full kitchen, bath and sleeping area all above our garage. Apartment has it’s own parking separate from main house. We are within walking distance to the public boat launch and near the historic Dixie if you want to catch a boat ride.

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, 197 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
The spacious suite features hardwood floors, a comfortable bed with light bedding, and a cozy red sofa. A wooden ceiling fan hangs above, and natural light floods in through the windows. An entertainment unit is positioned beside a decorative ottoman and a small dark chair.
Apartment in Winona Lake
4.97 out of 5 average rating, 300 reviews

Guesthouse Suites (A)

For business or pleasure you will find The Guesthouse Suites the ideal home base for The Village At Winona or Grace College. Both are a few steps away. Your view overlooks Spring Fountain Park. Within walking distance: Village shops and restaurants, Miller Sunset Pavilion for either ice skating or Saturday Farmers Market, Winona Lake Limitless Park and Splash pad, basketball, tennis, and pickleball courts, paved Heritage Trail for walking or biking, and mountain bike trails.

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