House vacation rentals in Chesterton
Find and book unique houses on Airbnb
Top-rated house rentals in Chesterton
Guests agree: these houses 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 house rentals
House rentals with a pool
Home in Michigan City
4.97 out of 5 average rating, 151 reviews5 Bedroom Luxury Home In Heart of Beachwalk Resort
Feb 22 – Mar 1
Home in Gary
4.93 out of 5 average rating, 125 reviewsBayless Dune Lodge at West Beach - Indiana Dunes!
Dec 21 – 28
Home in New Buffalo
4.91 out of 5 average rating, 267 reviewsFarmesque with a splash of modern
Dec 8 – 15
Home in Three Oaks
4.9 out of 5 average rating, 103 reviewsLuxe Life | Heated Pool | Hot Tub| Sleeps 10
Oct 15 – 22
Home in Union Pier
4.95 out of 5 average rating, 118 reviewsNew hot tub Heated pool & walk to Townline Beach
Feb 13 – 20
Home in Crown Point
5.0 out of 5 average rating, 25 reviewsLittle Pink House Downtown
Sep 14 – 21
Home in Michigan City
4.83 out of 5 average rating, 18 reviewsThe Keystone Ranch…The only house on the block!
May 7 – 14
Home in Michigan City
4.92 out of 5 average rating, 36 reviewsVip! 4BD 5 min to Lake, W pool heater.
Sep 12 – 19
Weekly house rentals
Home in Michigan City
4.91 out of 5 average rating, 138 reviewsHistoric Charmer: Walk to Casino, 2 miles to Beach
Jan 1 – 8
Home in Michigan City
4.92 out of 5 average rating, 282 reviewsCharming Getaway House near Beach
Jul 24 – 31
Home in Michigan City
4.96 out of 5 average rating, 373 reviewsDunefarmhouse Modern Country Escape
Jul 24 – 31
Home in Michigan City
4.85 out of 5 average rating, 105 reviewsThe Blue Herron- Dog friendly
Oct 4 – 11
Home in Michigan City
4.95 out of 5 average rating, 248 reviewsTRYON FARM MID-MODERN SPA IN THE WOODS
Jun 12 – 19
Home in Rochester
4.96 out of 5 average rating, 138 reviewsYour Country Home
Oct 9 – 16
Home in La Porte
4.95 out of 5 average rating, 136 reviews3 bedroom 2 bath Lake & Sunset Views
Sep 21 – 28
Home in Chesterton
5.0 out of 5 average rating, 18 reviewsBeautiful Vintage house
Mar 29 – Apr 5
Private house rentals
Home in Trail Creek
4.99 out of 5 average rating, 69 reviewsLeo Lodge
Nov 11 – 18
Home in Chesterton
4.84 out of 5 average rating, 56 reviewsNational Park Nature Lover's Paradise
Sep 12 – 19
Home in Porter
4.93 out of 5 average rating, 45 reviewsBrand New Dunes Escape
Dec 21 – 28
Home in Valparaiso
4.97 out of 5 average rating, 88 reviewsCozy Luxe Downtown Valparaiso Stay
Jun 4 – 11
Home in Porter
5.0 out of 5 average rating, 15 reviewsDunes Homestead - Near Dunes + Lake + Dog Friendly
May 26 – Jun 2
Home in Chesterton
4.94 out of 5 average rating, 17 reviews4 Season House
Jun 5 – 12
Home in Michigan City
4.99 out of 5 average rating, 70 reviewsFamily Friendly House near Beach/Casino/Shopping
Sep 12 – 19
Home in Valparaiso
4.82 out of 5 average rating, 68 reviewsCheerful three bedroom home in Downtown Valparaiso
Aug 29 – Sep 5
Quick stats about house rentals in Chesterton
Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.2K reviews
Nightly prices starting at
€ 37 before taxes and fees
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