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Kid-friendly vacation rentals in Chesterton

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Chesterton

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

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Home in Chesterton

4.8 out of 5 average rating, 255 reviews

South Shore Studio Apartment {National Park}

I have to warn u definitely not a hook up spot or party house!!! typically rise with rooster on this 5 acre country setting with a small fishing pond. 420 friendly .. Quiet hours 11 -8 generely some music playing and musicians are welcome !! if you happen to book on a sunday i host open mic in my Barn every sunday ..... pretty relaxed. Upon arriving turn into the driveway just passed my house and then right into the yard apartment is upstairs the door is open keys inside. ✌️

Home in Michigan City

4.94 out of 5 average rating, 427 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 f Per Airbnb guidelines I am disclosing we have cameras on exterior north/east of home with audio

Home in Portage

4.93 out of 5 average rating, 182 reviews

Newly Renovated with Finished Basement

This beautiful house is located near Lake Michigan in Northwest Indiana, less than 10 minutes from the expressway and toll road. There is a stainless steel kitchen, spa bathroom, finished basement and bar with sleeping capacity to accommodate two families. This is a smart home with Ring db, lights and thermostat controlled by your voice. We are less than an hour drive from downtown Chicago, and there are many great beaches nearby. Shopping and great dining options are also within a close drive.

Camper/RV in Porter

4.9 out of 5 average rating, 635 reviews

'Pool Barn Camper' w/Hot Tub near Indiana Dunes

Pool is open! Hot tub open all year! Fully equipped RV is parked in the driveway of our Pool Barn. RV sleeps 5, has bath w/shower, stove, microwave, heat & A/C, & running water all year. We are located minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hiking in the Indiana Dunes National Park along the Little Calumet River and the historic Bailley homestead is only 1 block away. You may also use our large pool, hot tub, grill, campfire, and playground area. No cleaning fee!

Tiny home in Michigan City

4.98 out of 5 average rating, 125 reviews

The Studio at the Dunes

Experience tiny living at the Studio after a day exploring the beautiful Indiana Dunes National Park! You will love this cozy tiny house with vaulted ceilings and modern amenities. Cool off with the mini-split air conditioner and relax on the sofa chaise after a long day in the sun. Staying in? Enjoy a board game while listening to some oldies on the record player, take a dip in the NEW hot tub, or relax on the hammocks by the fire pit in the secluded back yard. You’re sure to leave refreshed!

Home in Chesterton

4.9 out of 5 average rating, 114 reviews

Downtown Chesterton Cottage

Charming downtown house with a front porch, back deck & covered patio. Beautifully decorated with a small fenced in backyard. Minutes from the Indiana Dunes National Park and beaches. Near the South Shore Commuter train if you wish to visit Chicago without the drive and expense of parking. We are across from an active train track so if you like trains you can watch them from the front porch. Walk to restaurants, wineries and beer pubs. European market on Saturdays from May to end of October.

Cottage in Valparaiso

4.88 out of 5 average rating, 530 reviews

Flint Lake Cottage.

This is a rustic cottage with old world charm. There are 2 fireplaces,. The home sits on a hill overlooking a lake. The lake can be accessed from the back yard. - Pet free - Earth friendly cleaning products - Private beach & park access - Easy access to city center & university - One hour from downtown Chicago - National Lakeshore and Dunes State Park nearby - Local breweries & award winning restaurants - Biking & hiking trails near by - Wood fire places to enjoy in cold weather only

Barn in Michigan City

4.97 out of 5 average rating, 401 reviews

The Black Pearl Great Escape Spa & Art Shop

Check out our website! thegreatescapespah.com The Black 🖤 Pearl is perfect for a Special Occasion for the Evening. Book a Couples Massage @ 3p.m. & Check into your Spa Suite @ 4 p.m. Kick your feet Up & Order in.... Or Dine Out~ This quaint property is located in a woodsy setting 5 minutes from Lake Michigan. The keyless entry door to The Black Pearl is located on the East wall of The Great Escape. Upon entry the Black Pearl door will be directly in front of you. Mini Luxury awaits!

Condo in Portage

4.94 out of 5 average rating, 114 reviews

Cozy 1 bedroom condo on Marina near Lake Michigan

Come stay at this adorable one bedroom condo on the Marina near Lake Michigan! This condo has everything you need to enjoy a special getaway from everyday life. Conveniently located near the Indiana Dunes with the South Shoreline to Chicago directly across the street. Relax on the patio and enjoy watching the boats come and go as they please. Check out the drinks and food at the Marina Shores Yacht Club just a short walk away from this unit. This condo has everything you're looking for!

Guesthouse in Chesterton

4.97 out of 5 average rating, 150 reviews

Bro’s Place

Welcome if you like country life Bro’s place is the place to be...watching the sheep, chickens and wildlife on you back deck making dinner on the grill with a full kitchen. Pick your own veggies outside the back door when in season. You will find a welcome basket with snacks, wine and homemade soap in bathroom fresh eggs from our chickens when available if your planning to visit our Beautiful Indiana Dunes you’ll find everything you need..chairs, towels, cooler Queen size sofa sleeper

Guesthouse in New Buffalo

4.98 out of 5 average rating, 769 reviews

"Tiny House" Guest House Under the Oak Trees

"Tiny House" guest house located under large oak trees near the beach, and not far from I-94 and the Michigan state line. Vaulted ceiling, open feeling. Light and bright décor. Full bathroom, comfy couch, and other amenities. Polished concrete floor, whitewashed shiplap ceiling, hand-crafted oak furniture, suspended shelving. High ceilings, windows with southern exposure, front porch with siting chairs and a grill. Convenient charger for electric cars. Never a cleaning fee.

Home in Michigan City

4.92 out of 5 average rating, 222 reviews

Casinos, Shopping, Pets, and Parking a Plenty!

1 mile from BLUE CHIP CASINO - with its new SPORTS BOOK and is where the away team stays for NOTRE DAME FOOTBALL, 2 miles from the outlet mall, 7 blocks to the beach, and plenty of parking! 3 bedrooms (4 beds) and 1 bathroom. This is a great place regardless of the season and though in the city; it backs up to woods with lovely walking trails. The home also has hi speed internet/WiFi and HD cable television. Simple, practical home in a safe neighborhood - and it’s a bargain!

Vacation rentals for every style

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Stylish accommodations and amenities

Popular amenities for Chesterton kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Home in Valparaiso

4.95 out of 5 average rating, 123 reviews

Lakefront House, Pontoon, Deck, Fire Pit & More!

Home in Michigan City

4.96 out of 5 average rating, 167 reviews

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Home in Walkerton

4.9 out of 5 average rating, 103 reviews

Lakefront cottage on Koontz Lake

Home in Michigan City

4.96 out of 5 average rating, 390 reviews

Dunefarmhouse Modern Country Escape

Home in Michigan City

4.9 out of 5 average rating, 123 reviews

Bright pup friendly retreat +hot tub

Home in Michigan City

4.9 out of 5 average rating, 136 reviews

Big Beach Front House 8br 5ba Fireplace/Pit*WiFi*

Home in Beverly Shores

4.91 out of 5 average rating, 133 reviews

Dunes Vacation Rental

Home in De Motte

4.94 out of 5 average rating, 110 reviews

Home of 1888

Kid-friendly apartment rentals

Rental unit in Mishawaka

4.95 out of 5 average rating, 435 reviews

Private Entrance Guest Suite on the River

Rental unit in Michigan City

4.94 out of 5 average rating, 120 reviews

Urban chic apartment in downtown Michigan City

Rental unit in Michigan City

4.94 out of 5 average rating, 136 reviews

Charming apartment in Arts District

Rental unit in Valparaiso

5 out of 5 average rating, 129 reviews

ValpoVilla: Location, location, location!

Rental unit in Nappanee

4.96 out of 5 average rating, 165 reviews

Nappanee Loft

Rental unit in Granger

4.94 out of 5 average rating, 752 reviews

Wayback House

Rental unit in La Porte

4.93 out of 5 average rating, 481 reviews

Second Floor Apartment sitting on Pine Lake

Rental unit in Whiting

4.85 out of 5 average rating, 140 reviews

NEW! |Studio Apartment Whiting IN, United States#2

Kid-friendly condo rentals

Condo in Lincoln Park

4.99 out of 5 average rating, 245 reviews

❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

Condo in Andersonville

4.9 out of 5 average rating, 183 reviews

The Bright Retreat in Andersonville

Condo in St. Joseph

4.91 out of 5 average rating, 148 reviews

*Luxury condo on water in St Joseph, 2 queen beds*

Condo in East Rogers Park

4.91 out of 5 average rating, 127 reviews

Magnificent Place & A Parking Space

Condo in Lincoln Square

4.97 out of 5 average rating, 373 reviews

Lincoln Square Gem!

Condo in Bridgman

4.95 out of 5 average rating, 118 reviews

Luxury Loft downtown, close to Lake Michigan

Condo in East Rogers Park

4.93 out of 5 average rating, 215 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Condo in West Town

4.81 out of 5 average rating, 135 reviews

Cabin 207 at 747 Lofts

Quick stats about vacation rentals that are kid-friendly in Chesterton

Total rentals
20 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
2.9K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore