Family-friendly holiday rentals in Winona Lake

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.

4.99 out of 5 average rating, 105 reviews

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!

FamilyIndoor spacesValue

4.9 out of 5 average rating, 220 reviews

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.

FamilyIndoor spacesNearby

4.98 out of 5 average rating, 169 reviews

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.

KitchenIndoor spacesLong stay

4.97 out of 5 average rating, 373 reviews

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

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.

KitchenIndoor spacesParking

4.97 out of 5 average rating, 162 reviews

Cabin in Warsaw

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!

Indoor spacesFamilyTV

Guesthouse in Winona Lake

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.

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 !

FamilyKitchenBiking

5.0 out of 5 average rating, 282 reviews

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.

KitchenIndoor spacesLocation

4.94 out of 5 average rating, 164 reviews

4.85 out of 5 average rating, 140 reviews

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/Tesla charger- 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.

FamilyIndoor spacesBathroom

4.96 out of 5 average rating, 137 reviews

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.

Indoor spacesFamilyAmenities

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.

4.97 out of 5 average rating, 229 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.

FamilyIndoor spacesParking

Guesthouse in North Webster

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.

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!

Indoor spacesFamilyWi-Fi

4.98 out of 5 average rating, 281 reviews

4.96 out of 5 average rating, 274 reviews

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

Indoor spacesFamilyLong stay

Popular amenities for Winona Lake family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Shipping container in Columbia City

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.

The Steel Oasis-Container Home w/ Hot Tub!

KitchenIndoor spacesCheck-in

4.94 out of 5 average rating, 237 reviews

5.0 out of 5 average rating, 109 reviews

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

FamilyKitchenAccuracy

4.95 out of 5 average rating, 386 reviews

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

FamilyIndoor spacesOutdoor spaces

5.0 out of 5 average rating, 48 reviews

The Tulip House

Indoor spacesKitchenHospitality

5.0 out of 5 average rating, 8 reviews

Home in Pierceton

Lakefront Retreat! Spacious & Cozy

Indoor spacesKitchenAmenities

4.92 out of 5 average rating, 90 reviews

Home in Leesburg

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

FamilyKitchenValue

Superhost

A bright living space is presented, featuring two light-colored chairs beside a small wooden table, adorned with a potted plant. A cozy throw blanket drapes over one chair. A dining area with white chairs and a wooden table is visible, complemented by framed artwork on the walls.

Home in Albion

Small Town Lake Getaway w/HOT TUB!

KitchenIndoor spacesDecor

4.8 out of 5 average rating, 76 reviews

4.94 out of 5 average rating, 35 reviews

A two-story lakefront home is presented, featuring large glass doors that allow for ample natural light. A patio area with seating is visible, complemented by a hammock and well-maintained landscaping. A grill is located nearby, enhancing the outdoor space along the water.

Home in Rochester

Spacious Lake House with a view!

KitchenFamilyView

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 216 reviews

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

KitchenFamilyBeach

Apartment in Columbia City

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.

The Ruby Slipper Suite A: Historic Downtown Apt

FamilyIndoor spacesCheckout

4.87 out of 5 average rating, 339 reviews

4.98 out of 5 average rating, 620 reviews

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)

Indoor spacesFamilyView

4.88 out of 5 average rating, 208 reviews

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

KitchenIndoor spacesBackyard

4.95 out of 5 average rating, 82 reviews

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

FamilyIndoor spacesOutdoor spaces

5.0 out of 5 average rating, 6 reviews

Walk to Grace, Lake, Village, Indoor Climbing Wall

Indoor spacesFamilyParks

4.97 out of 5 average rating, 95 reviews

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.

Apartment in Winona Lake

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

Indoor spacesFamilyCondition

4.95 out of 5 average rating, 38 reviews

Home in Warsaw

Oriole Retreat. House with Full Kitchen.

Indoor spacesKitchenCheck-in

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 132 reviews

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

Summer of Fun - Luxury Home, Pool, Hot Tub, Arcade

FamilyKitchenLaundry

4.89 out of 5 average rating, 272 reviews

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

FamilyIndoor spacesCheckout

4.95 out of 5 average rating, 57 reviews

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

Indoor spacesKitchenNearby

Superhost

Home in Cromwell

Biscayne Ln Retreat/Pool, Game Room & Wawasee Fun

FamilyCleanlinessAccuracy

5.0 out of 5 average rating, 3 reviews

4.96 out of 5 average rating, 79 reviews

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

Indoor spacesFamilyHospitality