Chesterton Vacation Rentals, Vacation Home Rentals & More


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1 / 16

5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool

  • 5
  • 20
  • 3 nights min

$995

Details

Great rentals within 30 miles that match your search

1 / 31

Beachfront Villa Slps 30, Chicago-40min, 2+ Ngt quotes NOT Accurate, please ask!

  • 6
  • 30
  • 2 nights min

$560

Details

1 / 10

Miller Beach Tree House in Indiana Dunes

  • 3
  • 6
  • Min stay varies

$110

Details

1 / 25

Beachfront Guesthouse Slps8, Chicago-40min, 2+Ngt Quotes NOT Accurate, pls. ask!

  • 2
  • 8
  • 2 nights min

$129

Details

1 / 29

Lux Beachfront Slps 19, Chicago-40min, 2+ Ngt quotes NOT accurate, please ask!

  • 4
  • 19
  • 2 nights min

$279

Details

1 / 33

Lux Beachfront Slps 29, Chicago-40min, 2+ Ngt quotes NOT accurate, Please ask!

  • 6
  • 29
  • 2 nights min

$409

Details

1 / 18

Il Giardino

  • 3
  • 8
  • 3 nights min

$230

Details

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1 / 16

Lighthouse apt. Great location right by Lighthouse Outlet Mall See the Sale!

  • 1
  • 3
  • 2 nights min

$100

Details

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1 / 16

Beautiful apt next to Lighthouse Outlet Mall

  • 1
  • 3
  • 2 nights min

$100

Details

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1 / 16

Lighthouse Apartment Rental

  • 2
  • 4
  • 2 nights min

$130

Details

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1 / 13

Beautiful apt. across from Lighthouse Mall

  • 1
  • 2
  • 2 nights min

$100

Details

1
1 / 8

Guest House in Private Gated Nudist Community

  • 1
  • 2
  • 2 nights min

$140

Details

6
1 / 14

Ideal Family Getaway Home! 2bed 2bath sleeps 6, golf cart included!

  • 2
  • 6
  • Min stay varies

$230

Details

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1 / 27

Family Friendly Cottage just steps to Sandcastle Park - Includes Golf Cart

  • 2
  • 8
  • Min stay varies

$300

Details

10
1 / 8

charming 1 bedroom house by stop 2 beach & casino

  • 1
  • 4
  • 2 nights min

$120

Details

1 / 11

Brand New Rehab! Beach Rental fits 6

  • 2
  • 6
  • Min stay varies

$200

Details

1 / 19

Brand New Rehab! Beach Rental Fits 12

  • 4
  • 12
  • Min stay varies

$400

Details

1 / 7

CONDO FOR RENT IN FLORIDA

  • 1
  • 4
  • 90 nights min

$57

Details

1 / 21

Steps from the beach, sleeps 12, off street parking ONLY 4 NIGHT MINIMUM!

  • 3
  • 12
  • Min stay varies

$300

Details

1 / 28

3BR Beach Cottage Steps to the Sandy Shores of Lake Michigan

  • 3
  • 6
  • Min stay varies

$300

Details

1 / 28

Sundancer has a Spectacular Rooftop Deck with Lake Views and Sleeps 20

  • 7
  • 20
  • Min stay varies

$750

Details

1 / 25

Savannah has Off Street Parking and is a Short Walk to the Beach

  • 3
  • 10
  • Min stay varies

$381

Details

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1 / 28

4BR 3BA Short Walk to Beach - New Furnishings 8/15

  • 4
  • 14
  • 2 nights min

$299

Details

1 / 20

5 Bedroom Dog Friendly Beachfront Cottage with Hot Tub and Lake Views

  • 5
  • 12
  • Min stay varies

$599

Details

1 / 22

Custom designed luxury with outdoor TV, Firepit and included coach house!

  • 4
  • 12
  • 2 nights min

$500

Details

1 / 14

Screened Porch, Extra Parking Sleeps 14

  • 4
  • 14
  • Min stay varies

$400

Details

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1 / 39

Sun King-August weeks available. Won't last long.

  • 7
  • 24
  • Min stay varies

$400

Details

1 / 19

Couples Getaway! Short stays allowed. Studio with Queen + HOT TUB

  • Studio
  • 2
  • Min stay varies

$149

Details

1 / 20

Paradise at the Beach

  • 2
  • 8
  • Min stay varies

$199

Details

1 / 23

Kid Friendly in Beachwalk Resort - Sheridan Beach,Pool and Parks

  • 2
  • 8
  • Min stay varies

$199

Details

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1 / 18

Beautiful Cottage Indiana Dunes Sheridan Beach

  • 3
  • 7
  • Min stay varies

$112

Details

1 / 20

5/4 Cottage, Corner Lot with extra Parking Centrally Located to Beach, & Pool

  • 5
  • 12
  • Min stay varies

$400

Details

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1 / 36

Moondance--Book Summer 2018 While You Can

  • 6
  • 16
  • Min stay varies

$350

Details

2
1 / 21

Huge Enclosed Porch, 2 Main Level Masters, Centrally Located, Extra Parking

  • 4
  • 10
  • Min stay varies

$429

Details

1 / 18

New for 2017, The Bostonian 2/2 Cottage at Beachwalk

  • 2
  • 4
  • Min stay varies

$189

Details

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1 / 19

Southern Belle

  • 5
  • 14
  • Min stay varies

$550

Details

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1 / 9

Mint Julep

  • 2
  • 6
  • Min stay varies

$200

Details

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1 / 11

Blueberry Cottage

  • 2
  • 6
  • Min stay varies

$250

Details

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