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Chesterton Vacation Rentals

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

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sweet Home in Chesterton, vacation rental in Chesterton
Sweet Home in Chesterton, vacation rental in Chesterton
Sweet Home in Chesterton, vacation rental in Chesterton

Sweet Home in Chesterton

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool, vacation rental in Chesterton
5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool, vacation rental in Chesterton
5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool, vacation rental in Chesterton

5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool

Rental Home
5 bedrooms
3 bathrooms
Sleeps 20
Match: Sleeps
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Secluded Hideaway in the Dunes, vacation rental in Chesterton
Secluded Hideaway in the Dunes, vacation rental in Chesterton
Secluded Hideaway in the Dunes, vacation rental in Chesterton

Secluded Hideaway in the Dunes

Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Classic Roomy Cottage.  Best walk-to-everything location., vacation rental in Chesterton
Classic Roomy Cottage.  Best walk-to-everything location., vacation rental in Chesterton
Classic Roomy Cottage.  Best walk-to-everything location., vacation rental in Chesterton

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Lake Shore Beach House.   
Across the alley from our stunning beach., vacation rental in Chesterton
Lake Shore Beach House.   
Across the alley from our stunning beach., vacation rental in Chesterton
Lake Shore Beach House.   
Across the alley from our stunning beach., vacation rental in Chesterton

Lake Shore Beach House. Across the alley from our stunning beach.

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Artistic Loft close to Lake Michigan beaches, craft breweries & outlet shopping, vacation rental in Chesterton
Artistic Loft close to Lake Michigan beaches, craft breweries & outlet shopping, vacation rental in Chesterton
Artistic Loft close to Lake Michigan beaches, craft breweries & outlet shopping, vacation rental in Chesterton

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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious, Fun and Family Friendly Beach Home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Family Home Near Downtown Valpo & University, vacation rental in Chesterton
Family Home Near Downtown Valpo & University, vacation rental in Chesterton
Family Home Near Downtown Valpo & University, vacation rental in Chesterton

Family Home Near Downtown Valpo & University

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Charming Lakefront Cottage in the Indiana Dunes, vacation rental in Chesterton
Charming Lakefront Cottage in the Indiana Dunes, vacation rental in Chesterton
Charming Lakefront Cottage in the Indiana Dunes, vacation rental in Chesterton

Charming Lakefront Cottage in the Indiana Dunes

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Indiana Dunes Beach Rental, vacation rental in Chesterton
Indiana Dunes Beach Rental, vacation rental in Chesterton
Indiana Dunes Beach Rental, vacation rental in Chesterton

Indiana Dunes Beach Rental

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Porter Beach Vacation Getway! Lake Michigan Beachside Home - Newly Remodeled, vacation rental in Chesterton
Porter Beach Vacation Getway! Lake Michigan Beachside Home - Newly Remodeled, vacation rental in Chesterton
Porter Beach Vacation Getway! Lake Michigan Beachside Home - Newly Remodeled, vacation rental in Chesterton

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Two Bedroom Apartment in town by The Lighthouse Outlet Mall, vacation rental in Chesterton
Two Bedroom Apartment in town by The Lighthouse Outlet Mall, vacation rental in Chesterton
Two Bedroom Apartment in town by The Lighthouse Outlet Mall, vacation rental in Chesterton

Two Bedroom Apartment in town by The Lighthouse Outlet Mall

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cozy and Charming Beach Getaway on Lovely Lake Michigan, vacation rental in Chesterton
Cozy and Charming Beach Getaway on Lovely Lake Michigan, vacation rental in Chesterton
Cozy and Charming Beach Getaway on Lovely Lake Michigan, vacation rental in Chesterton

Cozy and Charming Beach Getaway on Lovely Lake Michigan

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Escape elearning and working from home with a Lakefront Lakehouse with Pontoon!, vacation rental in Chesterton
Escape elearning and working from home with a Lakefront Lakehouse with Pontoon!, vacation rental in Chesterton
Escape elearning and working from home with a Lakefront Lakehouse with Pontoon!, vacation rental in Chesterton

Escape elearning and working from home with a Lakefront Lakehouse with Pontoon!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Rare Private Pool w/in 1.5 Blocks to the Beach!, vacation rental in Chesterton
Rare Private Pool w/in 1.5 Blocks to the Beach!, vacation rental in Chesterton
Rare Private Pool w/in 1.5 Blocks to the Beach!, vacation rental in Chesterton

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

Rental Home
5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
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Miller Beach Get Away, vacation rental in Chesterton
Miller Beach Get Away, vacation rental in Chesterton
Miller Beach Get Away, vacation rental in Chesterton

Miller Beach Get Away

Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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Charming Beach Front Cottages, vacation rental in Chesterton
Charming Beach Front Cottages, vacation rental in Chesterton
Charming Beach Front Cottages, vacation rental in Chesterton

Charming Beach Front Cottages

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Casa Blanca in Miller Beach, vacation rental in Chesterton
Casa Blanca in Miller Beach, vacation rental in Chesterton
Casa Blanca in Miller Beach, vacation rental in Chesterton

Casa Blanca in Miller Beach

Rental Home
6 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
More info
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Large Apartment By Lighthouse Outlet Mall in Town area of Michigan City, vacation rental in Chesterton
Large Apartment By Lighthouse Outlet Mall in Town area of Michigan City, vacation rental in Chesterton
Large Apartment By Lighthouse Outlet Mall in Town area of Michigan City, vacation rental in Chesterton

Large Apartment By Lighthouse Outlet Mall in Town area of Michigan City

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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DUE TO COVID-19, WE HAVE DECIDED NOT TO RENT FOR REMAINING 2020!, vacation rental in Chesterton
DUE TO COVID-19, WE HAVE DECIDED NOT TO RENT FOR REMAINING 2020!, vacation rental in Chesterton
DUE TO COVID-19, WE HAVE DECIDED NOT TO RENT FOR REMAINING 2020!, vacation rental in Chesterton

DUE TO COVID-19, WE HAVE DECIDED NOT TO RENT FOR REMAINING 2020!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lovely Home -Miller Beach - Indiana Dunes National Park, vacation rental in Chesterton
Lovely Home -Miller Beach - Indiana Dunes National Park, vacation rental in Chesterton
Lovely Home -Miller Beach - Indiana Dunes National Park, vacation rental in Chesterton

Lovely Home -Miller Beach - Indiana Dunes National Park

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Nice   beach   house, vacation rental in Chesterton
Nice   beach   house, vacation rental in Chesterton
Nice   beach   house, vacation rental in Chesterton

Nice beach house

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lakefront Family Retreat w/ Grill: Steps to Beach!, vacation rental in Chesterton
Lakefront Family Retreat w/ Grill: Steps to Beach!, vacation rental in Chesterton
Lakefront Family Retreat w/ Grill: Steps to Beach!, vacation rental in Chesterton

Lakefront Family Retreat w/ Grill: Steps to Beach!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Lux Beachfront Slps 29, Chicago-40min, 2+ Ngt quotes NOT accurate, Please ask!, vacation rental in Chesterton
Lux Beachfront Slps 29, Chicago-40min, 2+ Ngt quotes NOT accurate, Please ask!, vacation rental in Chesterton
Lux Beachfront Slps 29, Chicago-40min, 2+ Ngt quotes NOT accurate, Please ask!, vacation rental in Chesterton

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

Rental Home
6 bedrooms
5 bathrooms
Sleeps 27
Match: Sleeps
More info
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MODERN GEM, CLOSE TO DOWNTOWN VALPO AND VU, DUNES AND BEACHES, vacation rental in Chesterton
MODERN GEM, CLOSE TO DOWNTOWN VALPO AND VU, DUNES AND BEACHES, vacation rental in Chesterton
MODERN GEM, CLOSE TO DOWNTOWN VALPO AND VU, DUNES AND BEACHES, vacation rental in Chesterton

MODERN GEM, CLOSE TO DOWNTOWN VALPO AND VU, DUNES AND BEACHES

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Stunning Home (Sleeps 16) Hot Tub, Firepit, Large Yard -45 min to  Notre Dame, vacation rental in Chesterton
Stunning Home (Sleeps 16) Hot Tub, Firepit, Large Yard -45 min to  Notre Dame, vacation rental in Chesterton
Stunning Home (Sleeps 16) Hot Tub, Firepit, Large Yard -45 min to  Notre Dame, vacation rental in Chesterton

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
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Beautiful  apt next to Lighthouse Outlet Mall, vacation rental in Chesterton
Beautiful  apt next to Lighthouse Outlet Mall, vacation rental in Chesterton
Beautiful  apt next to Lighthouse Outlet Mall, vacation rental in Chesterton

Beautiful apt next to Lighthouse Outlet Mall

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Cape Cod Close to County Line Orchard and 80/94 Hobart Merrillville Valparaiso, vacation rental in Chesterton
Cape Cod Close to County Line Orchard and 80/94 Hobart Merrillville Valparaiso, vacation rental in Chesterton
Cape Cod Close to County Line Orchard and 80/94 Hobart Merrillville Valparaiso, vacation rental in Chesterton

Cape Cod Close to County Line Orchard and 80/94 Hobart Merrillville Valparaiso

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Lighthouse apt. Great location right by Lighthouse Outlet Mall See the Sale!, vacation rental in Chesterton
Lighthouse apt. Great location right by Lighthouse Outlet Mall See the Sale!, vacation rental in Chesterton
Lighthouse apt. Great location right by Lighthouse Outlet Mall See the Sale!, vacation rental in Chesterton

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Lovely Lake Michigan Beach Rental

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Two-Bedroom Apartment by Lighthouse Outlet Mall, vacation rental in Chesterton
Two-Bedroom Apartment by Lighthouse Outlet Mall, vacation rental in Chesterton
Two-Bedroom Apartment by Lighthouse Outlet Mall, vacation rental in Chesterton

Two-Bedroom Apartment by Lighthouse Outlet Mall

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Studio Apt with full kitchen next to The Lighthouse Outlet Mall in Town area, vacation rental in Chesterton
Studio Apt with full kitchen next to The Lighthouse Outlet Mall in Town area, vacation rental in Chesterton
Studio Apt with full kitchen next to The Lighthouse Outlet Mall in Town area, vacation rental in Chesterton

Studio Apt with full kitchen next to The Lighthouse Outlet Mall in Town area

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Your family adventure awaits! Private Kayak Launch New for 2020!, vacation rental in Chesterton
Your family adventure awaits! Private Kayak Launch New for 2020!, vacation rental in Chesterton
Your family adventure awaits! Private Kayak Launch New for 2020!, vacation rental in Chesterton

Your family adventure awaits! Private Kayak Launch New for 2020!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Amazing Views From Beachfront Unit In the Heart of the Indiana Dunes, vacation rental in Chesterton
Amazing Views From Beachfront Unit In the Heart of the Indiana Dunes, vacation rental in Chesterton
Amazing Views From Beachfront Unit In the Heart of the Indiana Dunes, vacation rental in Chesterton

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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Dunetop Beachfront Slps 30, Chicago-40min, 2+ Ngt quotes NOT accurate, Pls. Ask!, vacation rental in Chesterton
Dunetop Beachfront Slps 30, Chicago-40min, 2+ Ngt quotes NOT accurate, Pls. Ask!, vacation rental in Chesterton
Dunetop Beachfront Slps 30, Chicago-40min, 2+ Ngt quotes NOT accurate, Pls. Ask!, vacation rental in Chesterton

Dunetop Beachfront Slps 30, Chicago-40min, 2+ Ngt quotes NOT accurate, Pls. Ask!

Rental Home
6 bedrooms
4 bathrooms
Sleeps 26
Match: Sleeps
More info
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Studio apt. across from Lighthouse Outlet Mall, vacation rental in Chesterton
Studio apt. across from Lighthouse Outlet Mall, vacation rental in Chesterton
Studio apt. across from Lighthouse Outlet Mall, vacation rental in Chesterton

Studio apt. across from Lighthouse Outlet Mall

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Indiana Dunes Beach Getaway Sleeps 12 close to casinos and train stations, vacation rental in Chesterton
Indiana Dunes Beach Getaway Sleeps 12 close to casinos and train stations, vacation rental in Chesterton
Indiana Dunes Beach Getaway Sleeps 12 close to casinos and train stations, vacation rental in Chesterton

Indiana Dunes Beach Getaway Sleeps 12 close to casinos and train stations

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Beachfront Guesthouse Slps 8, Chicago-40min, 2+ Ngt quotes NOT accurate, ask!, vacation rental in Chesterton
Beachfront Guesthouse Slps 8, Chicago-40min, 2+ Ngt quotes NOT accurate, ask!, vacation rental in Chesterton
Beachfront Guesthouse Slps 8, Chicago-40min, 2+ Ngt quotes NOT accurate, ask!, vacation rental in Chesterton

Beachfront Guesthouse Slps 8, Chicago-40min, 2+ Ngt quotes NOT accurate, ask!

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Miller Beach and Indiana Dunes National Park Vacation House, vacation rental in Chesterton
Miller Beach and Indiana Dunes National Park Vacation House, vacation rental in Chesterton
Miller Beach and Indiana Dunes National Park Vacation House, vacation rental in Chesterton

Miller Beach and Indiana Dunes National Park Vacation House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Ideal Family Getaway Home! 2bed 2bath sleeps 6, golf cart included!, vacation rental in Chesterton
Ideal Family Getaway Home! 2bed 2bath sleeps 6, golf cart included!, vacation rental in Chesterton
Ideal Family Getaway Home! 2bed 2bath sleeps 6, golf cart included!, vacation rental in Chesterton

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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NEW! Stylish Home w/ Elevated Deck, Walk to Beach!, vacation rental in Chesterton
NEW! Stylish Home w/ Elevated Deck, Walk to Beach!, vacation rental in Chesterton
NEW! Stylish Home w/ Elevated Deck, Walk to Beach!, vacation rental in Chesterton

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Indiana Dunes Beach Getaway Home, vacation rental in Chesterton
Indiana Dunes Beach Getaway Home, vacation rental in Chesterton
Indiana Dunes Beach Getaway Home, vacation rental in Chesterton

Indiana Dunes Beach Getaway Home

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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DunesWalk Inn - Vacation Rental, vacation rental in Chesterton
DunesWalk Inn - Vacation Rental, vacation rental in Chesterton
DunesWalk Inn - Vacation Rental, vacation rental in Chesterton

DunesWalk Inn - Vacation Rental

Condo/Apartment
5 bedrooms
5 bathrooms
Sleeps 19
Match: Sleeps
More info
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Urban living, close to malls, beach, in between Chicago and Michigan, quiet, vacation rental in Chesterton
Urban living, close to malls, beach, in between Chicago and Michigan, quiet, vacation rental in Chesterton
Urban living, close to malls, beach, in between Chicago and Michigan, quiet, vacation rental in Chesterton

Urban living, close to malls, beach, in between Chicago and Michigan, quiet

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Prime Lake Michigan Beach House - Indiana Dunes, vacation rental in Chesterton
Prime Lake Michigan Beach House - Indiana Dunes, vacation rental in Chesterton
Prime Lake Michigan Beach House - Indiana Dunes, vacation rental in Chesterton

Prime Lake Michigan Beach House - Indiana Dunes

Rental Home
2 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Beach front property with sunset view., vacation rental in Chesterton
Beach front property with sunset view., vacation rental in Chesterton
Beach front property with sunset view., vacation rental in Chesterton

Beach front property with sunset view.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Miller Beach - Indiana Dunes Family Getaway, vacation rental in Chesterton
Miller Beach - Indiana Dunes Family Getaway, vacation rental in Chesterton
Miller Beach - Indiana Dunes Family Getaway, vacation rental in Chesterton

Miller Beach - Indiana Dunes Family Getaway

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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LUXURY BEACH HOUSE IN DUNES NATIONAL PARK with 40ft POOL, GARDEN & OPTIONAL BOAT, vacation rental in Chesterton
LUXURY BEACH HOUSE IN DUNES NATIONAL PARK with 40ft POOL, GARDEN & OPTIONAL BOAT, vacation rental in Chesterton
LUXURY BEACH HOUSE IN DUNES NATIONAL PARK with 40ft POOL, GARDEN & OPTIONAL BOAT, vacation rental in Chesterton

LUXURY BEACH HOUSE IN DUNES NATIONAL PARK with 40ft POOL, GARDEN & OPTIONAL BOAT

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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The Eagles Nest, vacation rental in Chesterton
The Eagles Nest, vacation rental in Chesterton
The Eagles Nest, vacation rental in Chesterton

The Eagles Nest

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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