Family-friendly vacation rentals in Shipshewana

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.

4.94 out of 5 average rating, 454 reviews

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)

KitchenFamilyBathroom

4.97 out of 5 average rating, 464 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!

KitchenFamilyValue

The exterior of a red and stone house is showcased, featuring a deck that extends to a small green area with a putting green. Decorative red, white, and blue bunting adorns a black fence in the foreground. A bright blue sky with scattered clouds is visible above.

4.88 out of 5 average rating, 98 reviews

Little Red Hen *NEW* in 2024

Enjoy a stylish experience at this centrally-located downtown gem. BRAND NEW for 2024 with the most unique space in the downtown shopping district including a putting green! By day it’s a designers dream with creative sitting spaces throughout the house. At night the custom Murphy beds transform this house into a peaceful dreamland. Watch the world go by from the comfort of the interior swing while sipping on locally roasted coffee & JoJo’s Pretzels. Perfect for girlfriend getaways, families.

Indoor spacesKitchenCheck-in

4.96 out of 5 average rating, 164 reviews

A compact kitchen area is visible, featuring wooden cabinetry and a light-colored counter. A dining table with four upholstered chairs sits adjacent. Soft lighting and a decorative clock contribute to the welcoming atmosphere. The flooring is finished in a light wood look, enhancing the space's openness.

Camper/RV in Middlebury

1-bedroom RV, in a quiet spot for couples getaway

Enjoy the sounds of nature when you stay in this unique place. This unit is on the grounds of Teaberry Wood Products... In the heart of Amish country... Rise n Roll bakery is less than a 1/2 mile from our location. The Pumpkine Vine bike trail is about a mile away, the attractions in Shipshewana and Middlebury are within 4 miles. A safe place for your children… If you prefer to stay at one of our local campgrounds, we will set up our unit for $50.00 plus you would need to pay the campground.

Indoor spacesKitchenHeating

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.

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.

FamilyIndoor spacesSleep quality

4.97 out of 5 average rating, 637 reviews

A spacious living area features comfortable seating arranged around a coffee table. A large television is mounted on the wall, and natural light filters in through the glass doors leading to a patio. Decorative plants add a touch of greenery.

4.97 out of 5 average rating, 130 reviews

The Frey House

PLEASE READ GUEST ACCESS BEFORE BOOKING..... Bring the whole family to this great place with lots of room for fun. Located just 5 minutes from Blue Gate Theater and the Michiana Event Center. Only 3 minutes to the down town shops which includes the Vanilla Bean Icecream shop. 45 minutes from Notre Dame. With in walking distance to the Pumpkin Vine bike trail. Wake up in the morning and make a fresh cup of coffee as you sit at the kitchen table watching the horse drawn buggies drive past .

KitchenFamilyQuiet

4.98 out of 5 average rating, 100 reviews

The exterior of The Joy House on Main showcases a historic porch with stylish rocking chairs and beautifully landscaped gardens. Inside, a cozy living area is highlighted by comfortable seating and natural light. Bedrooms feature relaxing designs, and the kitchen displays organized utensils and plants, enhancing the homey feel.

Home in Middlebury

Joy House on Main Luxe - Downtown Middlebury

Experience luxury at The Joy House on Main - a beautifully restored historical home from 1904. Now owned and operated by us, Wes & Chelsea, owners of Joyfully Said. Immerse yourself in the charm of the past while enjoying modern comforts. Located in the heart of downtown, you'll have easy access to the renowned Pumpkinvine Trail, the charming shops, and top-notch local restaurants. Only 10 minutes away from Shipshe, this is the perfect destination for a small-town getaway with loved ones.

FamilyIndoor spacesCondition

4.93 out of 5 average rating, 230 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 + couch

Indoor spacesKitchenBiking

A cozy sleeping area features a spacious bed dressed in soft linens, flanked by nightstands with stylish lamps. Natural light filters through two windows, illuminating the warm wall paneling and complementing the neutral tones of the room.

5.0 out of 5 average rating, 106 reviews

Newly Renovated Home-Comfort in Quiet Shipshewana

Welcome to your peaceful retreat in the heart of Shipshewana! This newly renovated ranch-style home is tucked away on a quiet street, offering the perfect blend of comfort, style, and small-town charm! Step inside to discover a warm, thoughtfully decorated space with modern finishes and cozy touches throughout. Whether you’re in town to explore the famous flea market, visit local Amish shops, or simply unwind, this beautifully updated home is the perfect place to relax!

KitchenIndoor spacesBackyard

4.96 out of 5 average rating, 399 reviews

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.

FamilyIndoor spacesNearby

4.96 out of 5 average rating, 381 reviews

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!

Indoor spacesFamilyCondition

Guest suite in Middlebury

A modern kitchen area is highlighted by a large central island with a white countertop. Exposed brick walls add character, while vintage signage provides a nostalgic touch. A cozy seating arrangement features a small chair and a fireplace TV setup against the wall.

Mullet's Speed Shop

Refresh and relax at this newly constructed guest suite! Mullet's Speed Shop is conveniently located just 3 minutes from the famous Das Dutchman Essenhaus Restaurant and Bakery, less than 10 miles from the quaint shops of Shipshewana, and an easy 40 minute drive to Notre Dame (for the football fans). Take a bike ride or a peaceful walk on the Pumpkinvine Nature Trail less than 2 miles away. Nestled in the heart of Amish country, enjoy the buggies passing by!

Indoor spacesFamilySleep quality

5.0 out of 5 average rating, 178 reviews

Popular amenities for Shipshewana family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 790 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.

Home in Howe

Amazing Views Lakehouse with Kayaks

KitchenFamilyComfort

4.96 out of 5 average rating, 294 reviews

A hot tub is situated under a wooden pergola, with an expansive view of rolling pastureland and an open sky. Sunlight filters through fluffy clouds, creating a relaxing atmosphere for guests to unwind and enjoy nature.

Home in Middlebury

KitchenFamilyHot tub

Superhost

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

KitchenIndoor spacesHeating

4.9 out of 5 average rating, 245 reviews

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, 174 reviews

Farmhouse Sleeps 12+ Guests! Starlink Internet!

FamilyKitchenHot tub

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

FamilyKitchenOutdoor spaces

5.0 out of 5 average rating, 157 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

KitchenFamilyDecor

5.0 out of 5 average rating, 113 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

Indoor spacesFamilyLocation

Superhost

The historic Kownover Farmstead is surrounded by lush greenery, with a charming stone facade visible through vibrant trees. The large yard features well-maintained grass and various plants, creating a serene and secluded atmosphere for guests to enjoy.

Home in Granger

The Kownover (Conover) Farmstead

KitchenIndoor spacesHot tub

4.78 out of 5 average rating, 138 reviews

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 123 reviews

Home in White Pigeon

Secluded forest retreat with view

KitchenIndoor spacesAccess

4.99 out of 5 average rating, 140 reviews

An outdoor firepit surrounded by four black chairs sits on a grassy area near the water. A private pier is visible in the background, along with boats docked at the shore. A large willow tree offers shade beside the peaceful lake.

Cabin in Colon

Long Lake Cabin | Private Pier + 65’ Shoreline

Indoor spacesFamilyOutdoor spaces

4.9 out of 5 average rating, 137 reviews

Home in Sturgis

Lake House with a view

KitchenIndoor spacesCheckout

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, 620 reviews

The Villa Goshen (Exclusive Use/All Guest Spaces)

Indoor spacesKitchenLaundry

4.91 out of 5 average rating, 198 reviews

Home in Jones

2 story house 3 Bedrooms Cozy house Jones, Mi

FamilyIndoor spacesLayout

4.93 out of 5 average rating, 378 reviews

A spacious king bed is adorned with fresh white linens, accented by a decorative brightly colored throw. A decorative pillow adds a touch of pattern. A bedside table with a lamp and a decorative vase is situated nearby, offering both functionality and style.

Home in Constantine

Large Home - King - Sauna - Ski - Amish - Winery

FamilyIndoor spacesWalkability

4.95 out of 5 average rating, 311 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

Indoor spacesFamilyBathroom

Vacation home in Cassopolis

Four white Adirondack chairs are arranged on a grassy area, facing the lake. The calm blue water reflects the white clouds in the sky, with tree-lined hills visible in the background. A kayak and small boat are anchored nearby, adding to the serene lakeside setting.

Modern SW Michigan Lakefront Home w/Fireplace ⛷

KitchenFamilyBackyard

4.95 out of 5 average rating, 101 reviews

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

Indoor spacesFamilyPool

4.98 out of 5 average rating, 208 reviews

An aerial view showcases a fenced-in pool area surrounded by lush green lawns and mature trees. A small patio with outdoor seating is visible beside the pool. The gravel driveway leads to the property, with an adjacent structure and a pergola enhancing the outdoor space.

Guesthouse in Cassopolis

Cottage for two with hot tub!

KitchenIndoor spacesCheckout

4.99 out of 5 average rating, 245 reviews

Home in Vandalia

Private, Country Charm, Tiny Pool, Romantic, Quiet

KitchenIndoor spacesBreakfast

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.

4.94 out of 5 average rating, 63 reviews

Whitehouse Retreat! Pool - Hot Tub - 1GB WIFI

KitchenFamilyAccess

5.0 out of 5 average rating, 8 reviews

Home in Middlebury

Middlebury Getaway with In Ground Pool/Hot Tub

FamilyAccuracyHot tub

An entertainment room features a pool table and a foosball table, with a cozy seating area designed for relaxation. A spacious hot tub is shown outside, accompanied by scenic views during sunset. The warm tones of the living space invite comfort and leisure.

4.95 out of 5 average rating, 81 reviews

Cozy/HotTub/Pool/WIFI/KingBed/GameRoom/PoolTable

KitchenFamilyAccess

Superhost

An aerial view of the property showcases a spacious layout surrounded by lush greenery. An outdoor pool and tennis court are visible, along with a winding waterway. Nearby houses reflect a tranquil neighborhood ambiance, enhancing the property's secluded feel.

Home in Mishawaka

Luxury 6BR Summer Retreat | Pools + Sports Court

Indoor spacesFamilyBathroom

4.69 out of 5 average rating, 202 reviews