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Chesterton Rentals

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Price range

Per night

$10 - $500

Rental types

Chesterton Rentals

85 Houses

5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool

Chesterton house

5 bedrooms / 3 bathrooms / sleeps 20

Price per night from

$995

1 / 16

Great rentals within 20 miles that match your search

Moondance--Huge Open Concept in Central Beachwalk

Michigan City house

6 bedrooms / 3 bathrooms / sleeps 16

“Great location with great amenities” Loved the house. Great floor plan for large families and extended family. Loved the boardwalk to the beach and the trail around the lake. The kids liked the basketball court and the play area. The office was he

Responds fast! avg. 1 hour 14 minutes

Price per night from

$351

1 / 36

Walk to beach + 3 Outdoor decks and private off-street parking

Michigan City house

3 bedrooms / 2 bathrooms / sleeps 16

Price per night from

$495

1 / 45

Mint Julep

Michigan City house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$151

1 / 9

Serene 4BR LaPorte House w/Private Deck & Views

LaPorte house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 10 minutes

Price per night from

$150

1 / 25

Southern Belle

Michigan City house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$551

1 / 19

Il Giardino

Michigan City house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$229

1 / 18

Steps from Lake Michigan beach, sleeps 12, private off street parking

Michigan City house

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$199

1 / 19

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

Michigan City cottage

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$300

1 / 45

Beautifully Renovated 'Pinebrook Cottage' 2BR 1BA

New Buffalo house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 27 minutes

Price per night from

$251

1 / 23

Lake front house 4 bedroom Pier to dock your boat! Gorgeous view!

LaPorte house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$201

1 / 24

Charming Kid Friendly Cottage by Park 2/2 Sleeps 7 and includes golf cart

Michigan City house

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$219

1 / 26

On the beach with rooftop Great VIEWS!! Lake Michigan in your Back yard

Michigan City townhouse

3 bedrooms / 3 bathrooms / sleeps 16

Price per night from

$326

1 / 41

New Custom Home in Beachwalk Resort w/ Golf Cart BEACH, POOL, TENNIS

Michigan City house

5 bedrooms / 3 bathrooms / sleeps 11

Price per night from

$429

1 / 35

Across from the pool & Dog Friendly

Michigan City house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$425

1 / 24

My Blue Heaven

Michigan City house

6 bedrooms / 6 bathrooms / sleeps 16

Price per night from

$600

1 / 22

Guest House in Private Gated Nudist Community

Valparaiso house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$139

1 / 2

Grand Beach Home w/Pool & Hot Tub on Lake Michigan

Michiana house

6 bedrooms / 4 bathrooms / sleeps 16

Responds fast! avg. 22 minutes

Price per night from

$256

1 / 27

Picturesque beach home with pool table, view of Lake Kai plus a golf cart

Michigan City house

3 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$495

1 / 30

Poseidon--Beachwalk's Largest Home. The King of Beachwalk.

Michigan City house

8 bedrooms / 6 bathrooms / sleeps 27

Responds fast! avg. 1 hour 14 minutes

Price per night from

$451

1 / 41

Kid Friendly home in Beachwalk Resort - Walk to Beach, Pool, Tennis, Parks ++

Michigan City cottage

2 bedrooms / 1 bathroom / sleeps 8

Price per night from

$179

1 / 24

Great Family Beachwalk Resort home with great Kai Lake View - Fun decor

Michigan City house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$325

1 / 29

Everything Is New From Beds To Kitchen Cabinets

New Buffalo cottage

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 10 minutes

Price per night from

$226

1 / 24

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

Michigan City apartment

1 bedroom / 1 bathroom / sleeps 3

“Great stay!!” This apartment was perfect for our vacation. The location is great (right by the outlets and many restaurants)! The kids loved it and Darlene was a wonderful host (thanks for the cookies!!) I would highly recommend this rental to anyo

Responds fast! avg. 2 hours 32 minutes

Price per night from

$125

1 / 16

Beautiful apt. across from Lighthouse Mall

Michigan City apartment

1 bedroom / 1 bathroom / sleeps 2

“I love it!” Had an amazing weekend away it was perfect! Busy everyday doing something fun, got to enjoy the beach, the mall, had really good tasting food and everyone was super nice around town!

Responds fast! avg. 2 hours 32 minutes

Price per night from

$125

1 / 13

Watch the sun set on Sheridan Beach, Lake Michigan.

Michigan City house

6 bedrooms / 3 bathrooms / sleeps 18

Price per night from

$399

1 / 23

Stunning 7 Bedroom, 5 Master Suits W/ Private Baths & Outdoor Living Space!

Michigan City house

7 bedrooms / 6 bathrooms / sleeps 23

Price per night from

$649

1 / 35

Miller Beach Tree House in Indiana Dunes

Gary house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$100

1 / 10

Putting Green, Beach, Pool, Kayaking, Basketball- Fun for all ages included!

Michigan City house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$189

1 / 19

charming 1 bedroom house by stop 2 beach & casino

Michigan City house

1 bedroom / 2 bathrooms / sleeps 4

“Near the beach and shopping” This 1 bedroom home was just right for our needs. Very clean and updated. Sleeps 4 comfortably. About a 4 block walk to the beach and 1/2 mile from casino, outlet mall, and restaurants. New Buffalo about 20 minutes up the

Price per night from

$140

1 / 8

Conveniently Located Hidden Gem in Griffith/Gary Completely Renovated

Griffith house

3 bedrooms / 1 bathroom / sleeps 7

Price per night from

$119

1 / 19

Pistachio's Paradise 1.5 min walk to the beach!

Michigan City house

3 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$497

1 / 20

Colorado Place

Merrillville house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$99

1 / 26

Dune Farmhouse

Long Beach house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$251

1 / 6

5-Bedroom Single Family Home

Bellwood house

5 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$201

1 / 6

4 bed 2 bath Chicagoland Home

Merrillville house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$139

1 / 29

CONDO FOR RENT IN FLORIDA

Fort Lauderdale condo

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$57

1 / 7

Miller Beach Mid-Century Modern National Dune Lakeshore Park

Portage apartment

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$201

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