Family-friendly holiday 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.
Holiday 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
9–16 Dec
Cottage in Union Pier
4.95 out of 5 average rating, 273 reviewsJ’s Beach House: Hot Tub & short walk to beach!
24 Sep – 1 Oct
Home in New Buffalo
4.85 out of 5 average rating, 493 reviewsDebs Michigan hot tub house, open all year
16–23 Mar
Home in Beverly Shores
4.91 out of 5 average rating, 128 reviewsDunes Vacation Rental
2–9 Jun
Home in South Bend
4.91 out of 5 average rating, 241 reviewsHot Tub|Backyard Oasis|Espresso Maker|Coffee Bar
18–25 Jan
Home in Sawyer
4.94 out of 5 average rating, 141 reviewsBeautifully eclectic Sawyer cottage
16–23 Mar
Cottage in Union Pier
4.96 out of 5 average rating, 173 reviewsDesigner Cottage Relax Beach Pool & Spa—Windjammer
13–20 Nov
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
29 Nov – 6 Dec
Family- and pet-friendly home rentals
Bungalow in New Buffalo
4.85 out of 5 average rating, 428 reviewsNew Buffalo Michigan Beach House!
6–13 Feb
Home in Michigan City
4.85 out of 5 average rating, 110 reviewsLakeshore Manor
28 Dec – 4 Jan
Home in Michigan City
4.9 out of 5 average rating, 339 reviewsBest Deal In Michigan City 1.3 miles to Beach
13–20 Aug
Home in South Bend
4.85 out of 5 average rating, 205 reviewsHome newly remodeled minutes from Notre Dame.
18–25 Jul
Guesthouse in Stevensville
4.98 out of 5 average rating, 276 reviewsRed Barn Lodge
13–20 Oct
Apartment in Culver
4.9 out of 5 average rating, 130 reviewsCountry woods setting 4 miles from Culver
19–26 Jun
Apartment in Chicago
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
2–9 Dec
Guest suite in Chicago
4.97 out of 5 average rating, 238 reviewsStylish Studio in Historic Logan Square
4–11 Oct
Family-friendly home rentals with a pool
Tiny home in Sawyer
4.8 out of 5 average rating, 122 reviewsAfter Dune Delight
24 Sep – 1 Oct
Home in Buchanan
4.91 out of 5 average rating, 195 reviewsBeautiful RETREAT in the country
18–25 Apr
Apartment in Chicago
4.76 out of 5 average rating, 203 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
14–21 Dec
Apartment in Mishawaka
4.98 out of 5 average rating, 53 reviewsSpacious, private apartment in country setting
6–13 Jun
Cottage in Long Beach
5.0 out of 5 average rating, 57 reviewsBeach Walk w/ Pond Views. Steps to Beach & Pool
4–11 Jan
Cottage in New Buffalo
4.71 out of 5 average rating, 14 reviewsNew Buffalo Home With Private Heated Pool!
4–11 May
Home in Three Oaks
4.99 out of 5 average rating, 83 reviewsFlamingo Ranch in gorgeous Lakeside MI
28 Jun – 5 Jul
Home in New Buffalo
5.0 out of 5 average rating, 64 reviewsModern Farmhouse - Walk to Downtown, beach & pool!
11–18 Nov
Quick stats about holiday rentals that are family-friendly in Chesterton
Total rentals
40 properties
Wi-Fi availability
40 properties include access to Wi-Fi
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
$67 NZD before taxes and fees
Destinations to explore
- Downtown Chicago Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- West Lafayette Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- Chicago Holiday rentals
- Family-friendly rentals United States
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- Pet-friendly rentals Chesterton
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