Family-friendly vacation rentals in Chesterton
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chesterton
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesterton family-friendly rentals
Family-friendly home rentals with a hot tub
Apartment in Stevensville
4.91 out of 5 average rating, 699 reviewsQuiet Grand Mere Coach House on Lake Michigan
Dec 23 – 30
Cottage in Union Pier
4.95 out of 5 average rating, 272 reviewsJ’s Beach House: Hot Tub & short walk to beach!
Oct 5 – 12
Home in Beverly Shores
4.91 out of 5 average rating, 128 reviewsDunes Vacation Rental
Sep 7 – 14
Home in New Buffalo
4.85 out of 5 average rating, 492 reviewsDebs Michigan hot tub house, open all year
Nov 14 – 21
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Apr 20 – 27
Condo in Chicago
4.98 out of 5 average rating, 233 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Jan 24 – 31
Home in Sawyer
4.94 out of 5 average rating, 141 reviewsBeautifully eclectic Sawyer cottage
Nov 2 – 9
Home in South Bend
4.91 out of 5 average rating, 241 reviewsHot Tub|Backyard Oasis|Espresso Maker|Coffee Bar
Aug 17 – 24
Family- and pet-friendly home rentals
Home in Michigan City
4.85 out of 5 average rating, 110 reviewsLakeshore Manor
Nov 28 – Dec 5
Home in Michigan City
4.9 out of 5 average rating, 339 reviewsBest Deal In Michigan City 1.3 miles to Beach
Aug 29 – Sep 5
Guesthouse in Stevensville
4.98 out of 5 average rating, 276 reviewsRed Barn Lodge
Feb 9 – 16
Home in South Bend
4.85 out of 5 average rating, 205 reviewsHome newly remodeled minutes from Notre Dame.
Jul 19 – 26
Apartment in Chicago
4.96 out of 5 average rating, 237 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Nov 3 – 10
Home in New Buffalo
4.95 out of 5 average rating, 212 reviewsAnna's Cottage
Nov 22 – 29
Apartment in Culver
4.9 out of 5 average rating, 129 reviewsCountry woods setting 4 miles from Culver
Aug 31 – Sep 7
Guest suite in Chicago
4.97 out of 5 average rating, 238 reviewsStylish Studio in Historic Logan Square
Sep 25 – Oct 2
Family-friendly home rentals with a pool
Tiny home in Sawyer
4.8 out of 5 average rating, 122 reviewsAfter Dune Delight
Sep 24 – Oct 1
Home in Buchanan
4.91 out of 5 average rating, 195 reviewsBeautiful RETREAT in the country
Mar 28 – Apr 4
Apartment in Chicago
4.76 out of 5 average rating, 203 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Feb 8 – 15
Apartment in Mishawaka
4.98 out of 5 average rating, 53 reviewsSpacious, private apartment in country setting
Sep 9 – 16
Cottage in Long Beach
5.0 out of 5 average rating, 57 reviewsBeach Walk w/ Pond Views. Steps to Beach & Pool
Aug 8 – 15
Cottage in New Buffalo
4.71 out of 5 average rating, 14 reviewsNew Buffalo Home With Private Heated Pool!
May 14 – 21
Home in Three Oaks
4.99 out of 5 average rating, 83 reviewsFlamingo Ranch in gorgeous Lakeside MI
Jun 28 – Jul 5
Townhouse in New Buffalo
4.94 out of 5 average rating, 89 reviewsDunescape Beach Retreat, Downtown New Buffalo
Jul 14 – 21
Quick stats about vacation rentals that are family-friendly in Chesterton
Total rentals
40 properties
Wifi availability
40 properties include access to wifi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Total number of reviews
1.9K reviews
Nightly prices starting at
G$8,363 GYD before taxes and fees
Destinations to explore
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