Family-friendly vacation rentals in Three Oaks

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Three Oaks

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

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Guest favorite

Cabin in Rolling Prairie

4.87 out of 5 average rating, 135 reviews

3+ acres of Privacy, Pup heaven!7 minutes 3~Oaks!

Hello! we are 10 minutes to Three Oaks, Mi. This town is divine and very fun~ restaurants, galleries, Journeyman Distillery, Antiquing & Warren Dunes (epic hiking, dog-beaching-as private or social as you like). My artsy, sunny and cozy home welcomes you! We back up to over 3 + acres of private woods, a fresh spring fed brook and seconds from some of the best biking roads in the midwest! My place is VERY private yet 10 minutes to 3 Oaks for an evening of fun, live music & shows @ The Acorn! .

Jul 18 – 25

R2,857 ZAR per night

Guest favorite

Home in Michigan City

4.94 out of 5 average rating, 403 reviews

Small Clean Home Near Beach, Casino, Outlet Mall

This cozy, clean home is located 2.9 miles to Beach, Outlet Mall, and Casino. Quiet neighborhood. Well maintained property. Perfect for a couple or business traveler. It is not child proof. It is not suitable for small children. There are open stairs that cannot be blocked. We do not accept pets. I have an autoimmune disease. I am allergic to pet dander We request drivers license of each guest. Per Airbnb guidelines I am disclosing we have cameras on exterior north/east of home with audio.

Oct 25 – Nov 1

R2,096 ZAR per night

Guest favorite

Cottage in Lakeside

4.99 out of 5 average rating, 101 reviews

Pebble Path Cottage - Less than a block to beach!

Charming vacation home in Harbor Country, only 75 miles from Chicago. The cottage is less than a block from a wide, sandy private association beach where you can walk for miles, swim, or relax on the shore. It is perfectly situated to visit local farm stands, wineries, breweries, restaurants, & state parks. No smoking and no pets, please. Please note, we only book week-long rentals during the summer months (Friday-Friday). Checkout our sister cottage next door - Morning Dove Cottage

Aug 23 – 30

R7,165 ZAR per night

Guest favorite

Cottage in Union Pier

4.93 out of 5 average rating, 284 reviews

Steps to the Beach! Screened in Porch & Firepit!

Location does not get any better than this! 90 second walk to one public beach access, and less than 5 minutes to a second! Enjoy a lazy day at the beach or head out to explore the area. It's just a quick trip to rent a kayak or paddle-board, do a bit of antiquing, golfing or climb a giant dune. There's no limit to amazing breweries, wineries, and restaurants. End your day relaxing on the giant screened-in porch or out by the firepit. What's not to love about Harbor Country!

Apr 7 – 14

R4,299 ZAR per night

Guest favorite

Guesthouse in Chesterton

4.91 out of 5 average rating, 315 reviews

"myhathouse" detached studio downtown Chesterton

Vaulted skylights allow natural light. Ksize bed. Futon opens into a bed. (DEEP cleaned to AirBnb COVID-19 disinfectant standards) Fully stocked kitchen, sm. bathroom w/ shower. Parking ft. of house, 1.5 M from Lake Michigan Shoreline, 2 blocks to 15th St. entry to Prairie-Dune Trail. European Market (May -Oct) each Saturday downtown. Fall season drives along U.S. HW 12 & 20 for foliage Winter day hikes, x-county skis trail, shopping trips to the Michigan City Outlet mall

Dec 20 – 27

R1,925 ZAR per night

Guest favorite

Cottage in Union Pier

4.95 out of 5 average rating, 274 reviews

J’s Beach House: Hot Tub & short walk to beach!

J's Beach House is < a 5 minute walk to the beach! My cottage is equipped with a private hot tub and fireplace. Enjoy the walkable town or jump in your car for a quick drive to any Harbor Country activity! Potential for rental with adjacent cottage "Riley's Retreat". *Please inquire about our other Airbnb cottage near downtown Union Pier. This cottage is a 2-bedroom plus kids loft, screen porch, hot tub, fire pit, plus walking distance to Townline Beach!

Oct 17 – 24

R5,795 ZAR per night

Guest favorite

Farm stay in Buchanan

4.92 out of 5 average rating, 358 reviews

Regenerative Farm - Wine, Beach, Cannabis

Regenerative Permaculture Farm at the heart of the Wine Trail and 15 minutes to Lake Michigan beaches! Take a tour to meet our dog, sheep, horses, rabbits, and chickens. Hit the beach, go wine tasting, browse the dispensaries. In the evening dine out or cook a meal in the well stocked kitchen. Ask us about seasonal produce offerings. We live in the second unit on the lower level, and are available to offer any assistance to provide you the best possible stay.

Jan 18 – 25

R3,280 ZAR per night

Guest favorite

Home in Three Oaks

4.96 out of 5 average rating, 154 reviews

The Getaway - Three Oaks - 3 BR 1.5 Bath

Explore the wonders of Michigan's Harbor Country while staying in our relaxing private home, The Getaway. A few minutes walk to charming shops, restaurants, and event venues including Journeyman Distillery, The Acorn Theater, and The Social Club in Three Oaks. Three Oaks is just a ten minute drive from the beautiful beaches of Lake Michigan and thirty-five minutes to Notre Dame. Enjoy the small town lifestyle and find your own moment to getaway.

Apr 28 – May 5

R4,415 ZAR per night

Guest favorite

Cottage in Three Oaks

4.97 out of 5 average rating, 227 reviews

Lily’s Cottage, steps from Journeyman and Acorn!

Lily’s Cottage - Three Oaks, Michigan. Just steps to Journeyman Distillery and all other village sites including: Acorn Theater, Featherbone Factory Mercantile, Vickers Theater, Staymaker, Galleries, Shops, Antiques, Dewey Cannon Park, Bike Rentals, Nelson's Saloon, Drier's Meats, Froelich's and more! We are a no contact self check in rental. We are local and available by phone, text or airbnb email if needed during your stay.

May 21 – 28

R4,364 ZAR per night

Guest favorite

Home in Rolling Prairie

4.96 out of 5 average rating, 173 reviews

Rustic Elegance in the Michiana area

NO EVENTS. 10 person max at all times. 3- block walk to a small shared lake and near a host of lovely spots: Breweries/Wineries, Dunes, Three Oaks, Frisbee Golf, and more. A gas fireplace for cold winter nights, an outdoor firepit, a hammock, grill, and outdoor seating/camping chairs. A short walk to the Nowhere Bar & Grill for great local food! Only 1 hour 15 minutes from Chicago. Sleeps 8 comfortably.

Jun 20 – 27

R4,744 ZAR per night

Guest favorite

Cottage in Three Oaks

4.9 out of 5 average rating, 105 reviews

Private, Sun-filled Union Pier Cottage

Sunny, private cottage set on a half-acre facing woodlands. Quick drive to everything - beaches, hiking, restaurants, wineries, breweries, etc. High-speed internet available and desk with two monitors. Please be advised: reservation requests from first-time AIRBNB renters will be declined. You must have rented through AIRBNB in the past and received a high rating.

Oct 14 – 21

R3,252 ZAR per night

Guest favorite

Apartment in Granger

4.94 out of 5 average rating, 710 reviews

Wayback House

Country setting. Apartment above our garage. Attached to our house. No Smoking. No Pets. No Parties. No shared space but with the shared wall, you will here sounds from our space including garage door, voices, kitchen noise, dogs may bark, etc. we try to keep noise levels down but we live here and you may hear us.

Jun 9 – 16

R1,471 ZAR per night