Family-friendly holiday rentals in Shipshewana

4.94 out of 5 average rating, 426 reviews

A single-story house is set on a green lawn, with a well-maintained front garden featuring pink flowering shrubs. The brick exterior complements the surrounding foliage, and a pathway leads to the front door, framed by a modest porch.

Home in Shipshewana

Davis Street in Shipshewana

Davis Street in Shipshewana, located in the heart of Shipshewana Indiana's Amish country. Very close to the Auction & Flea Market, and within walking distance to local theatre, shops and restaurants. We offer cozy and friendly accommodations for the perfect country getaway. A perfect place to relax and enjoy partaking of the local small town pleasures. Access to the Pumpkinvine Nature Hiking/Biking trail is just 1 mile. And just 40 miles from Notre Dame/South Bend. (for the Irish football fans)

4.96 out of 5 average rating, 886 reviews

The spacious living area features arched ceilings and large windows, allowing natural light to fill the room. Comfortable seating is arranged around a central coffee table, with a flat-screen TV mounted on the wall. The adjacent kitchen includes stainless steel appliances and cabinetry.

Apartment in Goshen

Half-Moon Cottage

Enjoy privacy in this beautifully handcrafted cottage with arched ceilings. The cottage is 2 miles from downtown Goshen - a vibrant small town with restaurants and shops. It's 1 mile from Goshen College, 45 minutes from Notre Dame and 25 minutes from the Amish town of Shipshewana. The cottage is beside a fruit, nut and berry orchard and gardens. It's adjacent to a city bike trail that links to the Pumpkinvine nature/bike trail. It's close to a train crossing (with whistle) and a busy street.

4.97 out of 5 average rating, 419 reviews

The exterior of the cabin features a rustic wooden facade with white horizontal stripes. Green window shutters frame four windows, contributing to a charming and inviting appearance. A covered porch supported by wooden beams offers a welcoming entryway.

Cabin in Shipshewana

Log Cabin

Are you looking for a quiet, relaxing and peaceful place to stay? Look no further, this little cabin is all that and more! These pictures do not do the cabin justice, we have heard this from so many guests that have stayed at our cabin! You will not be disappointed with your stay at our cabin. The kitchen is equipped with a stove, microwave, refrigerator and dishwasher. A front and back porch with beautiful views to drink a cup of coffee, read a book or relax! We hope you will come stay soon!

Guest suite in Shipshewana

A welcoming front porch features two rocking chairs positioned beside a small decorative table, adorned with bright pink flowers. Lush greenery is visible in nearby planters, while sunlit windows with green shutters complete the charming country setting.

4.97 out of 5 average rating, 539 reviews

Picket Fence Farm Private Guest Retreat Suite

Stay in a 2nd story private suite in a modern farmhouse where we reside on a family farm in Amish country. Guests have the entire 2nd floor: 2 bedrooms, a private bath, and a sitting room. You can watch Amish buggies drive by while you rock on the front porch, access shared patio spaces or sit by a creek. We have cows, goats & chickens. We're in the heart of Shipshewana Amish/Mennonite community, minutes from downtown Shipshewana & all it has. An authentic, comfortable country getaway.

4.95 out of 5 average rating, 713 reviews

Sunlight filters through trees, casting gentle shadows across the lush lawn. A serene lake reflects the sky, with a canoe and dock visible in the distance. A swing set and seating area are positioned to enjoy the tranquil views.

Cottage in Howe

Cozy Nest - Lakefront, Dock, Kayaks, Pet Friendly

The Cozy Nest is an adorable three-bedroom, pet-friendly cottage with amazing views of a quiet, no-wake lake. Enjoy the stunning view while your cares melt away in the hot tub. The kitchen is fully stocked and ready for your use. Fiber optic wifi will keep you connected. There are two bicycles available for exploring the surrounding countryside as well as a canoe, 3 kayaks, and paddle boat to use on the water. Shipshewana is a quick 15-mile drive away through beautiful Amish countryside.

4.96 out of 5 average rating, 530 reviews

A serene riverside view captures vibrant autumn foliage reflected in calm waters. Comfortable seating is arranged on a stone patio, overlooking the river, enhancing the tranquil outdoor experience. Sunlight dances on the water's surface, inviting relaxation and connection with nature.

Apartment in Mishawaka

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.

4.83 out of 5 average rating, 368 reviews

A comfortable living room is furnished with a dark sectional sofa and an ottoman. A television is positioned on a wooden stand, with a nearby door leading outside. Natural light filters in through the window, partially covered by sheer curtains. Wood flooring adds warmth to the space.

Apartment in Shipshewana

Basement Apartment *conveniently near Shipshewana*

Come stay in our private-access, BASEMENT apartment, while you visit our town of Shipshewana. Our home sits in the middle of 7 acres of woods. We love it here, and we hope you do too! Our goal, as your hosts, is to provide you with a reasonably priced, cozy space, where you feel like you are visiting a friend, not staying at a high end hotel. Small touches set us apart like laundry and light breakfast/snacks provided for stays that include Sundays (coffee is ALWAYS on at this house)

4.93 out of 5 average rating, 165 reviews

Tiny home in Shipshewana

Private Lake+Fire Pit+Sauna+Kayaks | Pine & Paddle

Welcome to Pine and Paddle — the perfect place to unplug, recharge, and reconnect with nature by the lake. Unwind at this cozy lakeside tiny home, perfect for couples, friends, or solo travelers seeking peace, nature, and a hint of adventure near downtown Shipshewana. 🔥 Campfire pad w/ firewood + lake views 🛶 Kayaks + fishing poles + private dock ♨️ Wooden barrel sauna for ultimate relaxation 🌳 Private lake, beach, & outdoor games 🛏️ Sleeps 5 w/ full-size bunks + sofa bed

4.97 out of 5 average rating, 311 reviews

A cozy studio apartment features a comfortable bed with soft linens, a wooden coffee table, and a light-colored chest of drawers. Natural light filters in through a nearby window, illuminating the space. A green armchair is positioned in one corner, adding to the inviting ambiance.

Loft in Shipshewana

Hidden Country Hide-A-Way

Come relax in our cozy, modern country, studio apartment. It is equipt with a fully stocked kitchenette, private bathroom, comfortable living space, large screen tv and office work space. Enjoy some of the most picturesque landscape Northern Indiana has to offer. We are just a 10 min walk from Stone Lake and have kayak rentals available upon request. We are conveniently located 8 miles from Shipshewana and Middlebury, IN and just a 40 minute drive from Notre Dame.

4.96 out of 5 average rating, 343 reviews

Home in Shipshewana

The Oasis in Shipshewana

Enjoy the benefits of a furnished home during your stay! The perfect spot to enjoy a quiet place yet very close to local attractions in Shipshewana. The Shipshewana Auction & Flea Market is within walking distance. This is an ideal house for families looking for an economical vacation stay. A large deck and backyard for you to enjoy the outdoors. Bring your bicycles and take a ride on the Pumpkinvine Nature hiking and biking trail nearby. No TV but no time to miss it!

4.95 out of 5 average rating, 248 reviews

A comfortable living area features two soft sofas positioned around a light area rug. Natural light enters through a large window adorned with patterned curtains. A modern television sits on a wooden stand, and a lamp is placed beside a side table.

Apartment in Howe

The Upper Room

A newly remodeled full above-garage apartment with private entrance and access to a one car garage with a secure key pad. Only 15 minutes from Shipshewana Trading Place which is home to the midwest's largest flea market, beautiful Pumpkinvine Nature Trail amid Amish inspired shops and cuisine. Minutes from Indiana toll road exit 121 this quiet wooded setting is a great choice for an extended stay or ideal for a special getaway.

4.99 out of 5 average rating, 385 reviews

A charming log cabin features a welcoming facade with large windows framed by wooden accents. The entrance is accessed via a stone pathway lined with landscaped garden beds, showcasing lush greenery and colorful plants. Surrounding trees provide a serene, natural setting.

Cabin in Middlebury

Cabin off 39 - Peaceful, private one bedroom cabin

Kick back and relax in this calm, stylish space. Nestled among the trees, it provides a quiet getaway from the chaos of life allowing you to recharge and renew. The main residence is approximately 400 feet from the cabin. The cabin is secluded and yet close to local attractions, restaurants, biking and nature trails. The Cabin has a total of 420 sq ft living space with 280 sq ft on the ground floor and a 140 sq ft bedroom loft.

Popular amenities for Shipshewana family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A modern farmhouse exterior is presented, featuring a metal roof and a wooden-paneled garage door. Lush greenery surrounds the structure, complemented by a large tree providing shade. A well-maintained driveway leads to the front entrance, creating a welcoming ambiance.

4.96 out of 5 average rating, 157 reviews

Farmhouse Sleeps 12+ Guests! Starlink Internet!

4.91 out of 5 average rating, 116 reviews

A serene view of a river, framed by lush greenery, with a spacious backyard featuring a deck and seating areas. The calm water reflects the surrounding trees, adding to the peaceful atmosphere. A well-maintained landscape enhances the outdoor experience.

Home in Bristol

River Retreat W/ HOT TUB/ Game room

4.94 out of 5 average rating, 361 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

4.96 out of 5 average rating, 156 reviews

A cozy living area features a plush green sectional sofa arranged around a small wooden table. Natural light floods in through large windows, highlighting the wooden ceiling with black beams. A serene reading nook by the window includes a soft cushion and decorative plants.

Home in Sturgis

Aframe; Lake; shared Hottub; pet friendly; low fee

4.95 out of 5 average rating, 39 reviews

Home in Elkhart

Treehouse Acres

4.95 out of 5 average rating, 103 reviews

A welcoming living area is presented, featuring a comfortable leather sofa and a cozy armchair. A round coffee table centers the space, accompanied by a patterned area rug. Natural light filters through sliding glass doors, revealing views of a private outdoor patio.

Home in South Bend

South Bend Getaway - Walk to Notre Dame!

5 out of 5 average rating, 120 reviews

A spacious log cabin is set amidst lush greenery, complemented by a stone pathway leading to the entrance. The porch features wooden railings and is adorned with American flags. Natural light filters through the surrounding trees, enhancing the serene outdoor environment.

Cabin in Edwardsburg

The Nest - Luxurious Cabin Retreat

4.96 out of 5 average rating, 105 reviews

The entrance to the A-frame cabin is framed by a distinctive stone facade, featuring a welcoming sign and neatly arranged potted plants. Grass surrounds the exterior, with shade provided by nearby trees, enhancing the inviting appearance of the entryway.

Cabin in Warsaw

Heart Jacuzzi · Kayaks · Firepit · Pier

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 297 reviews

The exterior of the newly remodeled home showcases a neatly arranged wooden deck with a railing. Comfortable outdoor furniture is positioned on the deck, while well-maintained greenery surrounds the home. A gentle slope leads to the entrance, enhancing accessibility.

Home in South Bend

Home newly remodeled minutes from Notre Dame.

4.83 out of 5 average rating, 103 reviews

A comfortable gray sofa occupies the living area, adorned with a patterned throw pillow and a soft blanket draped casually. A coffee table is positioned in front, with decorative items displayed. Natural light streams in through a nearby window, enhancing the inviting space.

Home in Nappanee

The cozy cottage

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.

4.98 out of 5 average rating, 253 reviews

Modern Webster Lake cottage

4.86 out of 5 average rating, 109 reviews

A wooden sign displaying 'THE LOFT' is mounted on a post, set against a backdrop of a wooden fence with a natural finish. The area is surrounded by grass and scattered autumn leaves, adding a seasonal touch to the entrance.

Apartment in Niles

The Loft

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.

4.98 out of 5 average rating, 562 reviews

The Villa Goshen (Exclusive Use/All Guest Spaces)

4.9 out of 5 average rating, 165 reviews

The living room features two comfortable sofas, a coffee table with a decorative bowl, and a medium-sized television mounted on the wall. Large windows allow natural light to illuminate the space, creating a relaxed atmosphere. A ceiling fan is present for added comfort.

Home in Jones

2 story house 3 bedrooms Cozy house Jones, Mi

4.97 out of 5 average rating, 243 reviews

A bright living area showcases a combination of comfortable seating, including two armchairs and a sofa, arranged around a round coffee table. A dining table is positioned nearby, featuring a neutral tablecloth and a potted plant centerpiece. Light filters through sheer window curtains.

Bungalow in Elkhart

The Boho Bungalow

Farm stay in Kendallville

A welcoming exterior of a single-story home is depicted, featuring a covered porch with a bench. Soft exterior lighting illuminates the space, while a simple pathway leads from the porch to the surrounding grassy area. A white fence and trees are seen in the distance.

4.9 out of 5 average rating, 269 reviews

Stable View Home

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 106 reviews

A modern dining area features a wooden table surrounded by sleek black chairs. Behind it, a vibrant mural of South Bend adds color to the space. A cozy living area with a large sectional sofa and ample natural light can be seen through the open layout.

Home in South Bend

Large, Cozy, Theatre, Pool, Walk to ND Restaurants

A spacious dining area features a long wooden table surrounded by black chairs. A statement light fixture with multiple bulbs hangs overhead. A brick wall adds texture, while the background reveals the connection to the modern kitchen and living spaces.

5 out of 5 average rating, 33 reviews

Whitehouse Retreat! Pool - Hot Tub - 1GB WIFI

4.98 out of 5 average rating, 95 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

Hot Tub, Game Room, Fun Family Getaway, Clean!

4.96 out of 5 average rating, 68 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

4.91 out of 5 average rating, 11 reviews

Apartment in Cassopolis

Country Hideaway with Local Charm

5 out of 5 average rating, 25 reviews

A serene walkway is encircled by lush greenery and vibrant foliage, leading up to a charming house with large windows. A brick path gently winds through the garden, while a fence creates a sense of privacy. Outdoor seating is visible, inviting relaxation amidst the greenery.

Guesthouse in South Bend

Enchanting Pool House (2.2 miles from Notre Dame)

A spacious outdoor area features a pool surrounded by a concrete patio. Comfortable seating arrangements are placed under a canopy, with additional lounge chairs positioned nearby. Lush greenery provides a natural backdrop, enhancing the serene environment for relaxation and social gatherings.