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
Oct 17 – 24
Home in New Buffalo
4.91 out of 5 average rating, 265 reviewsFarmesque with a splash of modern
Jan 9 – 16
Home in Gary
4.93 out of 5 average rating, 125 reviewsBayless Dune Lodge at West Beach - Indiana Dunes!
Jun 21 – 28
Home in Three Oaks
4.9 out of 5 average rating, 103 reviewsLuxe Life | Heated Pool | Hot Tub| Sleeps 10
May 6 – 13
Home in Union Pier
4.95 out of 5 average rating, 119 reviewsNew hot tub Heated pool & walk to Townline Beach
Nov 5 – 12
Home in Crown Point
5.0 out of 5 average rating, 25 reviewsLittle Pink House Downtown
Oct 16 – 23
Home in Michigan City
4.83 out of 5 average rating, 18 reviewsThe Keystone Ranch…The only house on the block!
May 4 – 11
Home in Michigan City
4.97 out of 5 average rating, 31 reviewsHome near the lake with an inground pool
Feb 1 – 8
Weekly house rentals
Home in Michigan City
4.92 out of 5 average rating, 282 reviewsCharming Getaway House near Beach
May 27 – Jun 3
Home in Michigan City
4.96 out of 5 average rating, 373 reviewsDunefarmhouse Modern Country Escape
Aug 17 – 24
Home in Rochester
4.96 out of 5 average rating, 138 reviewsYour Country Home
Sep 26 – Oct 3
Home in Michigan City
4.95 out of 5 average rating, 248 reviewsTRYON FARM MID-MODERN SPA IN THE WOODS
Dec 15 – 22
Home in Michigan City
4.81 out of 5 average rating, 151 reviewsBoho Beach Getaway — short walk to the water!
May 14 – 21
Home in Whiting
4.8 out of 5 average rating, 225 reviewsWhiting Getaway
Oct 28 – Nov 4
Home in South Bend
4.83 out of 5 average rating, 111 reviewsCharming 3-bedroom home-Freshly remodeled-ND 5 mi.
Mar 20 – 27
Home in Chesterton
5.0 out of 5 average rating, 18 reviewsBeautiful Vintage house
Dec 23 – 30
Private house rentals
Home in Trail Creek
4.99 out of 5 average rating, 68 reviewsLeo Lodge
Feb 26 – Mar 5
Home in Porter
4.93 out of 5 average rating, 44 reviewsBrand New Dunes Escape
Dec 14 – 21
Home in Chesterton
4.84 out of 5 average rating, 56 reviewsNational Park Nature Lover's Paradise
Sep 8 – 15
Home in Chesterton
4.95 out of 5 average rating, 38 reviewsThe H'Art of Chesterton
Mar 20 – 27
Home in Chesterton
4.94 out of 5 average rating, 17 reviews4 Season House
Oct 29 – Nov 5
Home in Porter
5.0 out of 5 average rating, 15 reviewsDunes Homestead - Near Dunes + Lake + Dog Friendly
Nov 18 – 25
Home in Michigan City
4.99 out of 5 average rating, 70 reviewsFamily Friendly House near Beach/Casino/Shopping
Sep 10 – 17
Home in Michigan City
5.0 out of 5 average rating, 14 reviewsAfter Dune Delight
Aug 25 – Sep 1
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
G$8,363 GYD before taxes and fees
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- Rentals with a washer and dryer Chesterton
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