House vacation rentals in Chesterton
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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
Dec 6 – 13
Home in Gary
4.93 out of 5 average rating, 126 reviewsBayless Dune Lodge at West Beach - Indiana Dunes!
Dec 24 – 31
Home in New Buffalo
4.91 out of 5 average rating, 267 reviewsFarmesque with a splash of modern
Mar 15 – 22
Home in Union Pier
4.95 out of 5 average rating, 118 reviewsNew hot tub Heated pool & walk to Townline Beach
Nov 25 – Dec 2
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 Crown Point
5.0 out of 5 average rating, 25 reviewsLittle Pink House Downtown
Oct 13 – 20
Home in Michigan City
4.83 out of 5 average rating, 18 reviewsThe Keystone Ranch…The only house on the block!
Oct 8 – 15
Home in Michigan City
4.97 out of 5 average rating, 32 reviewsHome near the lake with an inground pool
Sep 3 – 10
Weekly house rentals
Home in Michigan City
4.95 out of 5 average rating, 248 reviewsTRYON FARM MID-MODERN SPA IN THE WOODS
Dec 26 – Jan 2
Home in Rochester
4.96 out of 5 average rating, 139 reviewsYour Country Home
Aug 11 – 18
Home in Michigan City
4.96 out of 5 average rating, 373 reviewsDunefarmhouse Modern Country Escape
Aug 18 – 25
Home in Michigan City
4.92 out of 5 average rating, 283 reviewsCharming Getaway House near Beach
May 28 – Jun 4
Home in Cedar Lake
4.84 out of 5 average rating, 211 reviewsVacation home on south end of Cedar Lake
Dec 1 – 8
Home in Whiting
4.8 out of 5 average rating, 227 reviewsWhiting Getaway
Nov 17 – 24
Home in Chesterton
5.0 out of 5 average rating, 18 reviewsBeautiful Vintage house
Mar 23 – 30
Home in Chesterton
4.95 out of 5 average rating, 40 reviewsBlue Birdhouse by the Beach - No Cleaning Fee
Apr 8 – 15
Private house rentals
Home in Chesterton
4.84 out of 5 average rating, 56 reviewsNational Park Nature Lover's Paradise
Sep 12 – 19
Home in Chesterton
4.94 out of 5 average rating, 17 reviews4 Season House
Nov 5 – 12
Home in Valparaiso
4.82 out of 5 average rating, 68 reviewsCheerful three bedroom home in Downtown Valparaiso
Oct 15 – 22
Home in Portage
5.0 out of 5 average rating, 35 reviewsIndiana Dunes, Beach, Chicago, Shopping Center
Oct 15 – 22
Home in Miller Beach
5.0 out of 5 average rating, 23 reviewsModern Oasis • 2 blocks to Beach • Rooftop Terrace
Oct 23 – 30
Home in Porter
4.93 out of 5 average rating, 45 reviewsBrand New Dunes Escape
Sep 6 – 13
Home in Chesterton
4.95 out of 5 average rating, 39 reviewsThe H'Art of Chesterton
Aug 11 – 18
Home in La Porte
4.96 out of 5 average rating, 24 reviewsSecluded 3-BR cottage w/ hot tub
Feb 18 – 25
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
R740 ZAR before taxes and fees
Destinations to explore
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