Holiday rentals in Leesburg

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!

Location · Value · Biking

Summer of fun Pool, Hot Tub, Huge Game Room CLEAN

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.

Value · Location · Grill

Dewart Lakefront Cottage

Escape to our charming Lake Cottage, nestled on the peaceful Dewart Lake in Syracuse, IN. Whether you're seeking a relaxing weekend or an adventurous getaway, this cozy retreat offers stunning lake views, beautiful sunrises and sunsets, private access on an all sport lake and all the comforts you need for a memorable stay anytime of the year. Enjoy the lake with kayaks, fishing from the pier and space for a boat, BBQ grill, smart TVs and campfire pit are just a few amenities we have to offer.

Family · Location · Kitchen

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.

Family · Location · Getting around

Cozy & Scenic Lakeside Retreat

Welcome to Shell Cottage on Shoe Lake, a charming retreat set by the lakefront offering breathtaking sunrises. Built in 1940, this 1 bedroom, 1 bath lovingly preserved and tastefully updated 424 sq ft cottage blends historic charm with modern comforts. A cozy layout with its original doors, windows and wood floors brings a nostalgic touch. Guests can make the most of lake life with included amenities - floe dock, paddle boat, and lift ready for your enjoyment. Perfect for a relaxing getaway!

Location · Sleep quality · Condition

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!

Location · Family · Sleep quality

Lakehouse, kayaks, dock, fishing, fence for pets!

Beautiful lakefront home on the Barbee chain of lakes. Small, but all you need!! This guesthouse features a kitchen, family room, firepit, dock for your boat, and a fenced in side yard for your dogs!! We supply 2 kayaks with lifejackets and a grill. King size bed in the bedroom! We have a loft for the kids that they will love!!! This house has the best views and best fishing on the chain! Must be 21 to book and show ID after booking confirmation. Plenty of parking. Come make some memories!!

Location · Family · Back garden

Lakefront Paradise Cozy Cottage

Welcome to our recently renovated Lakefront Paradise Cozy Cottage! Escape to your very own retreat offering 50 feet of prime waterfront on Sechrist Lake (Barbee Chain). Step outside and find yourself right next to the waters, where you can relax on the lakeside patio and soak in the stunning views featuring a nice sandy bottom, perfect for swimming and water activities. Whether you're looking for a peaceful getaway or a lively retreat, this lake cottage is ideal for making lasting memories.

Location · Family · Indoor spaces

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.

Family · Value · Grill

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!

Location · Family · Nearby

Lake Haven Cottage • Fun Summer Get Away

We invite you to come enjoy your time away at our delightful summer lake front cottage on Little Barbee Lake. Close proximity to Big Barbee Lake (all sports lake) Little Barbee is part of the Barbee Chain of Lakes with plenty of room to boat and fish. Bring your own boat or jet ski as the dock is steps away from the cottage. ••• Sunday AND Holiday check-ins may be available depending on our cleaning schedule! Please contact me and we'll do our very best to accommodate your schedule!

Family · Value · Comfort

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.

Family · Value · Indoor spaces