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
Flat in Stevensville
4.91 out of 5 average rating, 702 reviewsQuiet Grand Mere Coach House on Lake Michigan
12–19 Dec
Cottage in Union Pier
4.95 out of 5 average rating, 273 reviewsJ’s Beach House: Hot Tub & short walk to beach!
24 Sept – 1 Oct
Home in Beverly Shores
4.91 out of 5 average rating, 128 reviewsDunes Vacation Rental
3–10 Jun
Home in New Buffalo
4.85 out of 5 average rating, 493 reviewsDebs Michigan hot tub house, open all year
17–24 Nov
Home in South Bend
4.91 out of 5 average rating, 242 reviewsHot Tub|Backyard Oasis|Espresso Maker|Coffee Bar
18–25 Jan
Flat in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
27 Mar – 3 Apr
Cottage in Union Pier
4.96 out of 5 average rating, 173 reviewsDesigner Cottage Relax Beach Pool & Spa—Windjammer
13–20 Nov
Home in Sawyer
4.94 out of 5 average rating, 141 reviewsBeautifully eclectic Sawyer cottage
10–17 Feb
Family- and pet-friendly home rentals
Home in Michigan City
4.85 out of 5 average rating, 110 reviewsLakeshore Manor
27 Dec – 3 Jan
Home in Michigan City
4.9 out of 5 average rating, 339 reviewsBest Deal In Michigan City 1.3 miles to Beach
9–16 Aug
Home in South Bend
4.84 out of 5 average rating, 206 reviewsHome newly remodeled minutes from Notre Dame.
24–31 Jul
Apartment in Chicago
4.97 out of 5 average rating, 707 reviewsGreat location. Free parking.
Guest house in Stevensville
4.98 out of 5 average rating, 276 reviewsRed Barn Lodge
8–15 Apr
Flat in Chicago
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
18–25 Nov
Flat in Culver
4.9 out of 5 average rating, 130 reviewsCountry woods setting 4 miles from Culver
23–30 Aug
Home in Saint Joseph
4.89 out of 5 average rating, 276 reviewsCozy & Clean Entire Home in Saint Joseph
15–22 Nov
Family-friendly home rentals with a pool
Tiny home in Sawyer
4.8 out of 5 average rating, 122 reviewsAfter Dune Delight
16–23 Sept
Home in Buchanan
4.91 out of 5 average rating, 195 reviewsBeautiful RETREAT in the country
11–18 Aug
Flat in Chicago
4.76 out of 5 average rating, 203 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
21–28 Nov
Flat in Mishawaka
4.98 out of 5 average rating, 53 reviewsSpacious, private apartment in country setting
11–18 Aug
Cottage in Long Beach
5.0 out of 5 average rating, 57 reviewsBeach Walk w/ Pond Views. Steps to Beach & Pool
5–12 Jan
Cottage in New Buffalo
4.71 out of 5 average rating, 14 reviewsNew Buffalo Home With Private Heated Pool!
9–16 May
Townhouse in New Buffalo
4.94 out of 5 average rating, 89 reviewsDunescape Beach Retreat, Downtown New Buffalo
29 Sept – 6 Oct
Home in Three Oaks
4.99 out of 5 average rating, 83 reviewsFlamingo Ranch in gorgeous Lakeside MI
28 Jun – 5 Jul
Quick stats about holiday 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
£32 before taxes and fees
Destinations to explore
- Downtown Chicago Holiday rentals
- Lake Geneva Holiday rentals
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- West Lafayette Holiday rentals
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- Family-friendly rentals United States
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- Family-friendly rentals Chesterton
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