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. 25 – Jan. 1
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
Apr. 28 – May 5
Home in New Buffalo
4.85 out of 5 average rating, 493 reviewsDebs Michigan hot tub house, open all year
Feb. 12 – 19
Condo in Chicago
4.98 out of 5 average rating, 233 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Jan. 8 – 15
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Mar. 11 – 18
Home in Sawyer
4.94 out of 5 average rating, 141 reviewsBeautifully eclectic Sawyer cottage
Feb. 3 – 10
Cottage in Union Pier
4.96 out of 5 average rating, 173 reviewsDesigner Cottage Relax Beach Pool & Spa—Windjammer
Dec. 25 – Jan. 1
Family- and pet-friendly home rentals
Bungalow in New Buffalo
4.85 out of 5 average rating, 428 reviewsNew Buffalo Michigan Beach House!
Dec. 4 – 11
Cottage in Bridgman
4.79 out of 5 average rating, 154 reviewsCozy 1 BR & Loft Cottage: Lake Mich Dunes Wineries
May 6 – 13
Home in Michigan City
4.9 out of 5 average rating, 339 reviewsBest Deal In Michigan City 1.3 miles to Beach
Aug. 5 – 12
Guesthouse in Stevensville
4.98 out of 5 average rating, 276 reviewsRed Barn Lodge
Feb. 10 – 17
Cottage in Three Oaks
4.88 out of 5 average rating, 281 reviewsCottage with Character
Aug. 28 – Sep. 4
Apartment in Chicago
4.96 out of 5 average rating, 237 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Nov. 1 – 8
Apartment in Chicago
4.97 out of 5 average rating, 455 reviewsFully Furnished Apartment Wicker Park Free Parking
Jul. 21 – 28
Apartment in Culver
4.9 out of 5 average rating, 129 reviewsCountry woods setting 4 miles from Culver
Sep. 8 – 15
Family-friendly home rentals with a pool
Tiny homes 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
Jun. 15 – 22
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. 30 – Oct. 7
Cottage in Long Beach
5.0 out of 5 average rating, 57 reviewsBeach Walk w/ Pond Views. Steps to Beach & Pool
Feb. 5 – 12
Cottage in New Buffalo
4.71 out of 5 average rating, 14 reviewsNew Buffalo Home With Private Heated Pool!
May 14 – 21
Townhouse in New Buffalo
4.94 out of 5 average rating, 89 reviewsDunescape Beach Retreat, Downtown New Buffalo
Sep. 24 – Oct. 1
Home in Three Oaks
4.99 out of 5 average rating, 83 reviewsFlamingo Ranch in gorgeous Lakeside MI
Jun. 28 – Jul. 5
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
$55 CAD before taxes and fees
Destinations to explore
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