House holiday rentals in Winona Lake

Off The Beaten Pass II - Winona

“Off The Beaten Pass II” (directly next to ORIGINAL Off The Beaten Pass airbnb), has been cosmetically updated, maintaining its cottage style, character, & charm. Home away from Home... an inviting space to relax, unwind or do work in a spacious office area. Greenway walk+bike Trail is just feet away for exploring & connecting to other areas like Grace College. The Park, Beach, Shopping, Restaurants are about 1/3 mile walk. Watching Sunsets from any Winona green space is a treat to end the day!

Family · Value · Layout

Pool House On The Lake

The Pool House on the lake has several great features and is more the just a lake house. The house sets on a 5 acres wooded lot with a private gated drive. The 1950s home has the original bathrooms and kitchen but has been updated with great wifi ( for work or school) and new HD TVs through out. The view to the lake is one of a kind with its own private sandy beach and fire pit. No matter what the weather is there's something to do because this house also has a heated indoor pool(all year long).

Family · Value · Air conditioning

Walk to Grace, Lake, Village, Indoor Climbing Wall

Welcome to Wanderer's Rest, a spacious 5BR/3BA historic retreat in Winona Lake! Enjoy exclusive access to the Main & Upper Levels of our 1910 home. Perfect for up to 14 guests (all in real beds!). Ideal for wedding party lodging, retreats, and active family vacations. We feature a chef-ready kitchen, massive dining table, and the legendary Machu Picchu bunk room with an indoor climbing wall. Just a 5-minute walk to Grace College, the Village shops and restaurants, and the beach. Dog-friendly wit

Family · Location · Bathroom

The Villa Goshen (Exclusive Use/All Guest Spaces)

An unforgettable stay awaits! Spectacular waterfront views from the home and guest deck, with outstanding amenities and accommodations, this is The Villa Goshen. Booking allows exclusive use of all guest bedrooms, common spaces on the main & upper floors, and the wooden guest deck area off the kitchen. No parties unless pre-approved. Hosts live on site in a separate basement apartment. Easy access to Notre Dame (45 min), Middlebury (20 min), Nappanee (20 min), and 25 to Shipshewana (25 min).

Location · Value · Outdoor spaces

Winona Lake|Cozy 3 Bedroom Lake Front Home

This beautiful Winona lakefront home is spacious enough for the whole family: boasting a king bed, queen bed, and a full sized bunkbed. This home offers private access to a pier, where you can enjoy swimming, boating and stunning sunset views. Grill with family + friends on on the spacious patio. This 3 bedroom, 2 bath, open concept home has plenty of space to relax while enjoying all that Winona lake has to offer. Just a few minutes drive to The Village at Winona, splash pad, park, and trails!

Family · Location · Kitchen

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.

Value · Location · Amenities

The Tulip House

Nestled in the heart of charming Winona Lake, The Tulip House is a lovingly restored 1908 gem that beautifully combines historic character with modern comforts. Step inside to discover original hardwood floors, updated kitchen, 4 bedrooms, renovated bathrooms, and two inviting porches, complete with a relaxing hot tub. Just a short stroll away, you’ll find the village shops, restaurants, and breathtaking sunsets. This quaint town captured our hearts, and we’re thrilled to share it with you!

Location · Family · Beach

Relax 15 guests can enjoy Holidays & Everyday

Beautiful home in a quiet neighborhood on Barbee Chain of 7 Lakes ,Irish Lake Channel.Can be used for reunion corporate event birthday, bachelor bachelorette parties,fire pit Corn hole boards along with a fully stocked kitchen. Oklahoma Joe’s Gas &charcoal grill with a smoker box, 4 bedrooms 2 bath fenced in back yard for pets &kids.Pet fees apply. Parking for trailers trucks 2 Beautiful decks with gorgeous sunsets.Nice beach close by.Pontoons available to rent separately at the home.

Value · Family · Wi-Fi

Charming Lake House

New Cleaners- On Crystal Lake in Warsaw, Indiana is a 6-bedroom house fully stocked with everything you need for a comfortable stay- Wi-Fi,, a fully equipped kitchen, washer/dryer, and all the necessary linens/towels. The lake house is located on a no-wake lake, making it ideal for swimming, fishing, and paddleboarding. The house also has a kayak and canoe available for guests to use. After a day on the lake, guests can relax on the deck or around the fire pit. No pets. EV charger.

Location · Value · Check-in

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 · Parking

Scandihaus Cottage Fireplace+Deck, Near the Lake

Step into serenity at this thoughtfully curated Scandinavian-style cottage, nestled by the lake. The curated cottage features cozy linens, soft textures, and a warm, minimalist aesthetic that invites you to truly unwind. Sip your morning coffee on the deck while soaking in seasonal lake views, then curl up by the cozy fireplace as the evening sets in. Whether you’re reading a book or simply relaxing in the peaceful stillness, every corner is crafted for comfort & connection.

Family · Location · Outdoor spaces

Mineral Springs Hideaway

The Mineral Springs hideaway is a perfect peaceful getaway. Located two blocks from the beautiful Lake Winona and the The village of Winona a vibrant destination steeped in history. If you love to hike and bike the greenway is less than a block away. Grace College is a three minute walk. We know you’ll love experiencing a peaceful hideaway in northern Indiana.

Location · Family · Long stay