Family-friendly vacation rentals in Winona Lake

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!

The Shed Retreat

The Shed Retreat is a sacred space for anyone looking to shed their worries, fears, and busy schedules. Once a home for goats located in a secluded area on our property, it is now a peaceful garden oasis among the trees for those seeking a break from the norm. Inside, you can enjoy a cozy and relaxing place to lounge or rest. Outside, you can spend time around the fire pit, collect fresh eggs for breakfast, kayak on a nearby river, bike to local ice cream shops, or take a nap in a hammock.

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

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.

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.

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.

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.

Romantic Stay · 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!

Esterline Farms Cottage/ Brewery

Welcome to E Brewing Company at Esterline Farms Cottage. The first farmhouse brewery Air BNB in our state. We offer a beautiful new Cottage with spectacular views of our quaint hobby farm filled with miniature goats, chickens, rabbits, our resident paint horse. We have a full onsite brewery and taproom that is approximately 50 ft from the Cottage. It’s open Thurs, Fri, Sat, Sun. We are only 1/4 mile from South Whitley, 10 miles from Columbia City, and 20 miles from Fort Wayne and Warsaw.

Private Entrance Guest Suite on the River

Stay in our studio apartment suite with private exterior door entrance. Hosts live in the rest of the house. From the backyard you can fish, kayak/canoe, paddle board, enjoy a bonfire, grill, and relax by the river. There's a king memory foam bed, sleeper sofa, and 49" TV. Remote work friendly with spacious workspace desk, fast WIFI, and coffee. The closet has a mini food prep area with mini fridge and microwave, and grill out on back patio. It's a quick 15 min drive to Notre Dame.

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.

The Ruby Slipper Suite C: Historic Downtown Apt

A unique completely remodeled historic 1 bedroom with plenty of character and charm. Located on the corner of Line and Van Buren you can enjoy views of downtown out of the second story windows. The room is conveniently located within walking distance of coffee shops, restaurants, bakeries and a local brewery. The space has a theme of Wizard of Oz and we challenge you to find the hidden gems.