Chesterton Vacation Rentals | Book Now, Save Up to 30%

All in pricing: Taxes and fees included

Save $196

Preferred host

Entire home in Portage, IN

Nov 16 - 19

$341/night

5.0

1

3 bedrooms

10 guests

$1,317$1,121total

Save $133

Preferred host

Entire home in Michigan City, IN

Nov 16 - 19

$464/night

5.0

1

3 bedrooms

10 guests

$1,661$1,528total

Save $165

Preferred host

Entire townhouse in Gary, IN

Nov 16 - 19

$575/night

4.9

12

3 bedrooms

8 guests

$2,064$1,899total

Save $97

Preferred host

Entire home in Gary, IN

Nov 16 - 19

$341/night

4.5

10

3 bedrooms

11 guests

$1,218$1,121total

Save $95

Preferred host

Entire home in Gary, IN

Nov 16 - 19

$264/night

5.0

15

3 bedrooms

7 guests

$963$868total

Save $74

Preferred host

Entire home in Valparaiso, IN

Nov 16 - 19

$259/night

5.0

1

2 bedrooms

6 guests

$925$851total

Save $210

Preferred host

Entire home in Michigan City, IN

Nov 16 - 19

$732/night

4.7

6

5 bedrooms

14 guests

$2,628$2,418total

Save $77

Guests rave

Cottage in Michigan City, IN

Nov 17 - 20

$207/night

4.9

28

1 bedroom

4 guests

$767$690total

Save $66

House in Michigan City, IN

Nov 16 - 19

$228/night

4.9

7

3 bedrooms

5 guests

$827$761total

Save $285

House in Michigan City, IN

Nov 16 - 19

$299/night

5.0

18

3 bedrooms

6 guests

$1,279$994total

Save $158

Apartment in Michigan City, IN

Nov 16 - 19

$428/night

5.0

2

3 bedrooms

11 guests

$1,584$1,425total

Save $273

Vacation Rental in Michigan City, IN

Nov 16 - 19

$737/night

5.0

1

6 bedrooms

25 guests

$2,725$2,453total

Save $125

Apartment in Michigan City, IN

Nov 16 - 19

$432/night

5.0

2

3 bedrooms

14 guests

$1,563$1,438total

Save $413

Guests rave

House in Michigan City, IN

Dec 4 - Jan 3

$143/night

4.9

59

3 bedrooms

8 guests

$5,166$4,752total

Save $69

Guests rave

House in Michigan City, IN

May 1 - 4

$238/night

4.9

125

2 bedrooms

6 guests

Pay only $62 today

$860$791total

Save $67

House in Michigan City, IN

Nov 16 - 19

$180/night

4.0

1

2 bedrooms

4 guests

$666$599total

Save $92

Preferred host

Entire home in Michigan City, IN

Dec 23 - 26

$322/night

4.8

12

3 bedrooms

11 guests

$1,152$1,060total

Save $185

Unit 1 of 3

Duplex in Michigan City, IN

Nov 16 - 19

$456/night

5.0

15

4 bedrooms

12 guests

$1,701$1,516total

Save $91

Unit 2 of 3

Duplex in Michigan City, IN

Nov 16 - 19

$315/night

5.0

15

2 bedrooms

6 guests

$1,140$1,049total

Save $91

Unit 3 of 3

Duplex in Michigan City, IN

Nov 16 - 19

$315/night

4.8

17

2 bedrooms

6 guests

$1,140$1,049total

Save $361

House in Michigan City, IN

Dec 2 - Jan 1

$112/night

New

2 bedrooms

4 guests

$4,091$3,730total

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Map shows last minute vacation rentals in Chesterton