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Holiday Rentals in Chesterton

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50 rentals in Chesterton.
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Chesterton “Golf View Estate” Midwest  Great Lake Beaches & Trails Of The Dunes!, holiday rental in Chesterton

Chesterton “Golf View Estate” Midwest Great Lake Beaches & Trails Of The Dunes!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool, holiday rental in Chesterton

5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool

5 bedrooms
3 bathrooms
Sleeps 20
Match: Sleeps
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NEW! Quaint Chesterton Home in Walkable Location!, holiday rental in Chesterton

NEW! Quaint Chesterton Home in Walkable Location!

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Classic Roomy Cottage.  Best walk-to-everything location., holiday rental in Chesterton

Classic Roomy Cottage. Best walk-to-everything location.

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spacious, Fun and Family Friendly Beach Home, holiday rental in Chesterton

Spacious, Fun and Family Friendly Beach Home

4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Artistic Loft close to Lake Michigan beaches, craft breweries & outlet shopping, holiday rental in Chesterton

Artistic Loft close to Lake Michigan beaches, craft breweries & outlet shopping

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Dune Fine Is A Brand New Family Friendly Home Right On The Beach, holiday rental in Chesterton

Dune Fine Is A Brand New Family Friendly Home Right On The Beach

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Family Home Near Downtown Valpo & University, holiday rental in Chesterton

Family Home Near Downtown Valpo & University

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Beautiful New Home!   Book Now, Summer is filling up fast!!, holiday rental in Chesterton

Beautiful New Home! Book Now, Summer is filling up fast!!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Beach Cottage - 205 California Ave, holiday rental in Chesterton

Beautiful Beach Cottage - 205 California Ave

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Indiana Dunes Beach Rental, holiday rental in Chesterton

Indiana Dunes Beach Rental

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Charming Beachfront Home w/huge backyard,steps to beach!Recently renovated., holiday rental in Chesterton

Charming Beachfront Home w/huge backyard,steps to beach!Recently renovated.

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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'How You Dune?'- Lake Michigan Beach House Perfect For Large Groups!, holiday rental in Chesterton

'How You Dune?'- Lake Michigan Beach House Perfect For Large Groups!

7 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Porter Beach Vacation Getway! Lake Michigan Beachside Home - Newly Remodeled, holiday rental in Chesterton

Porter Beach Vacation Getway! Lake Michigan Beachside Home - Newly Remodeled

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Rare Private Pool w/in 1.5 Blocks to the Beach!, holiday rental in Chesterton

Rare Private Pool w/in 1.5 Blocks to the Beach!

5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Casa Blanca in Miller Beach, holiday rental in Chesterton

Casa Blanca in Miller Beach

6 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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Cozy and Charming Beach Getaway on Lovely Lake Michigan, holiday rental in Chesterton

Cozy and Charming Beach Getaway on Lovely Lake Michigan

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Beach Front Cottages, holiday rental in Chesterton

Charming Beach Front Cottages

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo, holiday rental in Chesterton

New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful  apt next to Lighthouse Outlet Mall, holiday rental in Chesterton

Beautiful apt next to Lighthouse Outlet Mall

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Vintage Cottage with Covid Protocols, holiday rental in Chesterton

Vintage Cottage with Covid Protocols

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Vintage Lake Michigan Beach Cottage: 4br+loft,3ba-Sleeps 17, holiday rental in Chesterton

Vintage Lake Michigan Beach Cottage: 4br+loft,3ba-Sleeps 17

4 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
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Big Cozy House In The Dunes (5bed/3.5bath plus loft) - Nested In Wooded Hillside, holiday rental in Chesterton

Big Cozy House In The Dunes (5bed/3.5bath plus loft) - Nested In Wooded Hillside

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Lighthouse apt. Great location right by Lighthouse Outlet Mall See the Sale!, holiday rental in Chesterton

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

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo, holiday rental in Chesterton

New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Walk to Lake Michigan Beach! Sleeps 12 - 14!, holiday rental in Chesterton

Walk to Lake Michigan Beach! Sleeps 12 - 14!

5 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Nice   beach   house, holiday rental in Chesterton

Nice beach house

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Two-Bedroom Apartment by Lighthouse Outlet Mall, holiday rental in Chesterton

Two-Bedroom Apartment by Lighthouse Outlet Mall

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lovely Lake Michigan Beach Rental, holiday rental in Chesterton

Lovely Lake Michigan Beach Rental

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Stunning Home (Sleeps 16) Hot Tub, Firepit, Large Yard -45 min to  Notre Dame, holiday rental in Chesterton

Stunning Home (Sleeps 16) Hot Tub, Firepit, Large Yard -45 min to Notre Dame

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Studio apt. across from Lighthouse Outlet Mall, holiday rental in Chesterton

Studio apt. across from Lighthouse Outlet Mall

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lake House on beach path, sleeps 12!, holiday rental in Chesterton

Lake House on beach path, sleeps 12!

2 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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5BD 2BA Cottage walking distance to Sheridan Beach & 30 min drive to Norte Dame, holiday rental in Chesterton

5BD 2BA Cottage walking distance to Sheridan Beach & 30 min drive to Norte Dame

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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A great time for a weekend get away!!!, holiday rental in Chesterton

A great time for a weekend get away!!!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Amazing Views From Beachfront Unit In the Heart of the Indiana Dunes, holiday rental in Chesterton

Amazing Views From Beachfront Unit In the Heart of the Indiana Dunes

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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1 Block off Beach with Lake Views, holiday rental in Chesterton

1 Block off Beach with Lake Views

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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People who have stayed here love this place and want to come back., holiday rental in Chesterton

People who have stayed here love this place and want to come back.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Brand New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo, holiday rental in Chesterton

Brand New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Minutes to beach, businesses and train!, holiday rental in Chesterton

Minutes to beach, businesses and train!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Miller Beach and Indiana Dunes National Park Vacation House, holiday rental in Chesterton

Miller Beach and Indiana Dunes National Park Vacation House

3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Indiana Dunes Beach Getaway Home, holiday rental in Chesterton

Indiana Dunes Beach Getaway Home

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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CONDO FOR RENT IN FLORIDA, holiday rental in Chesterton

CONDO FOR RENT IN FLORIDA

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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DunesWalk Inn - Vacation Rental, holiday rental in Chesterton

DunesWalk Inn - Vacation Rental

5 bedrooms
5 bathrooms
Sleeps 19
Match: Sleeps
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Dune our Thing- 1 block to beach with private parking and lake views!, holiday rental in Chesterton

Dune our Thing- 1 block to beach with private parking and lake views!

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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ON THE BEACH, holiday rental in Chesterton

ON THE BEACH

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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NEW! Stylish Home w/ Elevated Deck, Walk to Beach!, holiday rental in Chesterton

NEW! Stylish Home w/ Elevated Deck, Walk to Beach!

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lakefront Family Retreat w/ Grill: Steps to Beach!, holiday rental in Chesterton

Lakefront Family Retreat w/ Grill: Steps to Beach!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Well-Appointed Gary Home Few Blocks to Beach!, holiday rental in Chesterton

NEW! Well-Appointed Gary Home Few Blocks to Beach!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Creature Comforts at Catalpa, holiday rental in Chesterton

Creature Comforts at Catalpa

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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It's the Wright Farm, holiday rental in Chesterton

It's the Wright Farm

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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