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Family-friendly holiday rentals in Winona Lake

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Winona Lake

  • Total holiday rentals

    Explore 20 holiday rentals in Winona Lake

  • Nightly prices starting at

    Winona Lake holiday rentals start at $140 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,420 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Winona Lake holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winona Lake rentals

  • 5 Average rating

    Winona Lake stays are highly rated by guests – averaging 5 out of 5!

Top-rated family-friendly rentals in Winona Lake

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
The exterior of the cottage features a welcoming porch with seating, surrounded by green space and landscaped areas. A pathway leads to a carport. Amenities such as a fire pit and gas grill are visible, with clear access to walk and bike trails nearby.
Home 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!

4.99 out of 5 average rating, 103 reviews
Guest favourite
An indoor pool is surrounded by large windows, providing ample natural light and views of the outdoor landscape. The wooden ceiling features exposed beams, while a stone wall displays decorative elements. Comfortable lounge chairs are positioned nearby for relaxation.
Home in Roann

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).

4.88 out of 5 average rating, 269 reviews
Guest favourite
A log cabin with a welcoming front porch is surrounded by lush greenery. A gravel driveway leads up to the cabin, which features large windows and a rustic design. Natural light filters through the trees, enhancing the serene outdoor setting.
Cabin in North Webster

Dock of the Bay Fishing 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.

4.89 out of 5 average rating, 218 reviews
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

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.

4.98 out of 5 average rating, 169 reviews
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.
Flat in Warsaw

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.

4.97 out of 5 average rating, 373 reviews
Top guest favourite
A well-lit bedroom features two spacious beds dressed in white linens. Two bedside lamps with blue bases provide soft lighting, while framed artwork adorns the walls. A mirror reflects the tranquil setting, and a small table offers a cozy touch.
Guest house in Winona Lake

Guesthouse Suite (C)

Experience the rich history of lovely Winona Lake when you book your stay in our GuestHouse Suites. Next to the heart of the Village At Winona, just steps up to Grace College or a short walk to visit the shops and restaurants. Enjoy a relaxing afternoon on the patio with the views of Spring Fountain park. WL Limitless Park and public beach, splash pad, tennis, pickleball and basketball courts, paved walking/bike trails, challenging mountain bike trails, are all within walking distance !

5.0 out of 5 average rating, 281 reviews
Top guest favourite
An inviting pathway framed by vibrant fall foliage leads through the setting, with a logo for E Brewing Company prominently displayed. Soft golden and orange hues of autumn leaves create a warm backdrop for the marketing text highlighting the brewery and Airbnb's location.
Farm stay in South Whitley

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.

4.94 out of 5 average rating, 161 reviews
Top guest favourite
The exterior view of the home is displayed alongside a serene lake. The structure features a blend of outdoor decks with seating areas, large windows, and a well-maintained yard with trees offering shade, all set against a clear blue sky.
Home in Warsaw

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.

4.96 out of 5 average rating, 135 reviews
Guest favourite
A serene view of a lake at sunset displays vibrant shades of pink and purple reflected across the water surface. Silhouettes of trees line the horizon, providing a tranquil backdrop to the colorful sky.
Home in Warsaw

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.

4.86 out of 5 average rating, 139 reviews
Top 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

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.

4.96 out of 5 average rating, 227 reviews
Top guest favourite
A grey house with solar panels is seen alongside a driveway, featuring a parked white SUV. Lush orange flowers bloom prominently in the foreground, while multiple trees provide greenery in the background under a blue sky.
Guest house in North Webster

Modern Webster Lake cottage

This home has a great floor plan for 2-4 people with a small loft bed for a youngster. It has high end kitchen accessories and in-unit washer and dryer. Water softener for great water, maple hardwood floors and a front deck for outdoor barbecuing. Parking for 3 cars and a shed with lots of amenities including bikes and hammock for recreation and relaxing. New in 2024, new rug, blackout curtains and solar panels! EV charger free for guests!

4.97 out of 5 average rating, 278 reviews
Top guest favourite
A sandy lakefront area is visible, featuring several brown Adirondack chairs arranged in a circle around a fire pit. In the background, a wooden dock leads to a covered boat lift, with calm waters reflecting the clouds above.
Cottage in Warsaw

Lakewood Cottage on Winona Lake

Modern and light filled lakefront cottage on beautiful Winona Lake. Great views from the lakefront dining area. You walk in the front door and you feel surrounded by the water. Quiet neighborhood is great for biking and walks. You can access the Greenway trail a mile away which takes you to the Village of Winona. Check out our custom video on youtube, just copy and paste the below code into the youtube search bar. AMErvK41MSo

4.96 out of 5 average rating, 273 reviews

Popular amenities for Winona Lake family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favourite
Cabin in Warsaw

Romantic A-frame · HeartJacuzzi · Firepit · Kayaks

4.97 out of 5 average rating, 159 reviews
Top guest favourite
A modern shipping container home is set amidst a wooded landscape. The structure features large glass windows and a welcoming entryway. A daybed swing is visible on the porch, surrounded by lush green grass and tall trees, creating an inviting outdoor space.
Shipping container in Columbia City

The Steel Oasis-Container Home w/ Hot Tub!

4.94 out of 5 average rating, 236 reviews
Top guest favourite
A bright dining area is showcased, featuring a round table surrounded by four rattan chairs. A large window invites natural light, while delicate wallpaper adds a subtle texture. A chandelier hangs above, contributing to the cozy ambiance of the space.
Home in Nappanee

Charming Newly Renovated House | HOT TUB

5.0 out of 5 average rating, 104 reviews
Guest favourite
A hot tub bubbles gently on a spacious deck, framed by lush greenery. Comfortable seating arrangements, including a hanging chair and dining area, are positioned to enjoy views of the lake. String lights add a touch of ambiance against the clear sky.
Cottage in Wawaka

Cozy Lakefront Tiny Home w/ Hot Tub

4.95 out of 5 average rating, 382 reviews
Top guest favourite
The exterior of The Tulip House features a light blue facade with white trim, showcasing large windows and a front porch. The steps lead to a welcoming entrance, framed by a seasonal motif of fallen leaves on the ground.
Home in Winona Lake

The Tulip House

5.0 out of 5 average rating, 48 reviews
Guest favourite
Home in Leesburg

Lakefront, Pets, Hot Tub, dock, fishing, kayaks.

4.92 out of 5 average rating, 87 reviews
Guest favourite
Home in Pierceton

Lakefront Retreat! Spacious & Cozy

5.0 out of 5 average rating, 6 reviews
Guest favourite
An octagonal wooden table with seating for eight is set on the deck, surrounded by green grass and mature trees. A serene lake view is visible in the background, with boats dotting the water and warm sunlight filtering through the foliage.
Home in Bremen

Lake Of The Woods Sunset Shore - Notre Dame

5.0 out of 5 average rating, 19 reviews

Family- and pet-friendly home rentals

Top guest favourite
The image captures a serene lakeside sunset, where the sun sets behind a silhouette of trees. The golden reflections shimmer on the water's surface, creating a tranquil ambiance. A pier is visible on the right, offering a spot to enjoy the scenic views.
Home in Albion

D & J Lakefront Rental

4.97 out of 5 average rating, 477 reviews
Top guest favourite
A serene lake view is captured during sunset, with vibrant orange and pink hues reflected on the water. The surrounding trees frame the scene, while a private pier is visible at the foreground, inviting guests to relax and enjoy the natural beauty.
Cottage in North Webster

Webster Lakefront Updated Studio with Pier & Deck

4.94 out of 5 average rating, 216 reviews
Guest favourite
A cozy living area features a dark leather sofa adorned with colorful cushions. A unique coffee table made from a door rests on a textured rug. Natural light streams in through large windows, framed by bright yellow accents, enhancing the space's character.
Flat in Columbia City

The Ruby Slipper Suite A: Historic Downtown Apt

4.87 out of 5 average rating, 338 reviews
Top guest favourite
The historic Villa Goshen is showcased in a red brick design, framed by lush trees and gardens. The inviting entrance features elegant landscaping leading to a prominent door, with a beautiful view of the waterfront beyond the property.
Home in Goshen

The Villa Goshen (Exclusive Use/All Guest Spaces)

4.98 out of 5 average rating, 614 reviews
Guest favourite
A wooden deck is presented with a railing, leading from the house to the grassy area. Flowering plants are positioned along the edges, and stone borders add structure to the landscape. A large tree provides shade to the space, enhancing the outdoor setting.
Farm stay in Bremen

Old Fox Farm - Cozy Country

4.88 out of 5 average rating, 205 reviews
Guest favourite
Farm stay in Rochester

The Rentschler Farmhouse- 5 Acres of Relaxation

4.82 out of 5 average rating, 103 reviews
Top guest favourite
A bright bedroom features a spacious bed dressed in white linens, accented by a blue throw blanket. Natural light fills the room through large windows, with a stylish mirror and a decorative vase positioned nearby. A wooden dresser provides storage, and a cozy bench is placed at the foot of the bed.
Flat in Winona Lake

Cozy Winona Lake Apt. -Grace, The Village, & Lake!

4.97 out of 5 average rating, 92 reviews
Top guest favourite
A welcoming front porch features a wooden floor and white railings. Two comfortable chairs are positioned around a small table, inviting relaxation. The entrance is marked by a single door, and the porch provides a view of the grassy area beyond.
Bungalow in Winona Lake

Trail side in the heart of Winona Lake

4.95 out of 5 average rating, 80 reviews

Family-friendly home rentals with a pool

Top guest favourite
An aerial view captures a country retreat surrounded by farmland. A spacious yard includes an in-ground pool and a stocked pond, with winding pathways leading to the home. Colorful trees are positioned nearby, showcasing seasonal foliage against the expansive landscape.
Home in North Manchester

North Manchester Tranquil Retreat

4.95 out of 5 average rating, 56 reviews
Top guest favourite
The Bunkhouse is framed by a large tree and American flag. A landscaped garden with rocks and flowers enhances the inviting entrance. The rustic exterior is complemented by a metal roof, and seating is provided on a small patio area.
Farm stay in Rome City

Mirror Lake Bunkhouse

4.96 out of 5 average rating, 79 reviews
Superhost
Home in Cromwell

Biscayne Ln Retreat/Pool, Game Room & Wawasee Fun

Camper van/Motorhome in Pierceton

Bearfoot Bungalow

New place to stay
Top guest favourite
An indoor pool area is illuminated by natural light streaming through a transparent roof. A smooth slide stands beside the water, while comfortable seating is arranged to create a relaxing space. A basketball hoop is mounted near the pool, enhancing recreational opportunities.
Home in Goshen

Private Indoor Pool make memories all year long!

4.98 out of 5 average rating, 45 reviews

When is the best time to visit Winona Lake?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$178 SGD$184 SGD$184 SGD$212 SGD$240 SGD$273 SGD$273 SGD$267 SGD$217 SGD$210 SGD$210 SGD$200 SGD
Avg. temp-4°C-2°C4°C10°C16°C21°C23°C22°C18°C12°C5°C-1°C

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