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Chesterton Holiday Apartments

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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!, holiday rental in Chesterton
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!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sweet Home in Chesterton, holiday rental in Chesterton
Sweet Home in Chesterton, holiday rental in Chesterton
Sweet Home in Chesterton, holiday rental in Chesterton

Sweet Home in Chesterton

Holiday Rental House
3 bedrooms
2 bathrooms
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, holiday rental in Chesterton
5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool, holiday rental in Chesterton

5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 20
Match: Sleeps
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Secluded Hideaway in the Dunes, holiday rental in Chesterton
Secluded Hideaway in the Dunes, holiday rental in Chesterton
Secluded Hideaway in the Dunes, holiday rental in Chesterton

Secluded Hideaway in the Dunes

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 14
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., holiday rental in Chesterton
Classic Roomy Cottage.  Best walk-to-everything location., holiday rental in Chesterton

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

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

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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, holiday rental in Chesterton
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

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Family Home Near Downtown Valpo & University, holiday rental in Chesterton
Family Home Near Downtown Valpo & University, holiday rental in Chesterton
Family Home Near Downtown Valpo & University, holiday rental in Chesterton

Family Home Near Downtown Valpo & University

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Charming Lakefront Cottage in the Indiana Dunes, holiday rental in Chesterton
Charming Lakefront Cottage in the Indiana Dunes, holiday rental in Chesterton
Charming Lakefront Cottage in the Indiana Dunes, holiday rental in Chesterton

Charming Lakefront Cottage in the Indiana Dunes

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Indiana Dunes Beach Rental, holiday rental in Chesterton
Indiana Dunes Beach Rental, holiday rental in Chesterton
Indiana Dunes Beach Rental, holiday rental in Chesterton

Indiana Dunes Beach Rental

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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, holiday rental in Chesterton
Porter Beach Vacation Getway! Lake Michigan Beachside Home - Newly Remodeled, holiday rental in Chesterton

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Two Bedroom Apartment in town by The Lighthouse Outlet Mall, holiday rental in Chesterton
Two Bedroom Apartment in town by The Lighthouse Outlet Mall, holiday rental in Chesterton
Two Bedroom Apartment in town by The Lighthouse Outlet Mall, holiday rental in Chesterton

Two Bedroom Apartment in town by The Lighthouse Outlet Mall

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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, holiday rental in Chesterton
Cozy and Charming Beach Getaway on Lovely Lake Michigan, holiday rental in Chesterton

Cozy and Charming Beach Getaway on Lovely Lake Michigan

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Escape elearning and working from home with a Lakefront Lakehouse with Pontoon!, holiday rental in Chesterton
Escape elearning and working from home with a Lakefront Lakehouse with Pontoon!, holiday rental in Chesterton
Escape elearning and working from home with a Lakefront Lakehouse with Pontoon!, holiday rental in Chesterton

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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!, holiday rental in Chesterton
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!

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Miller Beach Get Away, holiday rental in Chesterton
Miller Beach Get Away, holiday rental in Chesterton
Miller Beach Get Away, holiday rental in Chesterton

Miller Beach Get Away

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Charming Beach Front Cottages, holiday rental in Chesterton
Charming Beach Front Cottages, holiday rental in Chesterton
Charming Beach Front Cottages, holiday rental in Chesterton

Charming Beach Front Cottages

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Casa Blanca in Miller Beach, holiday rental in Chesterton
Casa Blanca in Miller Beach, holiday rental in Chesterton
Casa Blanca in Miller Beach, holiday rental in Chesterton

Casa Blanca in Miller Beach

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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Large Apartment By Lighthouse Outlet Mall in Town area of Michigan City, holiday rental in Chesterton
Large Apartment By Lighthouse Outlet Mall in Town area of Michigan City, holiday rental in Chesterton
Large Apartment By Lighthouse Outlet Mall in Town area of Michigan City, holiday 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
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DUE TO COVID-19, WE HAVE DECIDED NOT TO RENT FOR REMAINING 2020!, holiday rental in Chesterton
DUE TO COVID-19, WE HAVE DECIDED NOT TO RENT FOR REMAINING 2020!, holiday rental in Chesterton
DUE TO COVID-19, WE HAVE DECIDED NOT TO RENT FOR REMAINING 2020!, holiday rental in Chesterton

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely Home -Miller Beach - Indiana Dunes National Park, holiday rental in Chesterton
Lovely Home -Miller Beach - Indiana Dunes National Park, holiday rental in Chesterton
Lovely Home -Miller Beach - Indiana Dunes National Park, holiday rental in Chesterton

Lovely Home -Miller Beach - Indiana Dunes National Park

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Nice   beach   house, holiday rental in Chesterton
Nice   beach   house, holiday rental in Chesterton
Nice   beach   house, holiday rental in Chesterton

Nice beach house

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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!, holiday rental in Chesterton
Lakefront Family Retreat w/ Grill: Steps to Beach!, holiday rental in Chesterton

Lakefront Family Retreat w/ Grill: Steps to Beach!

Holiday Rental House
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!, holiday rental in Chesterton
Lux Beachfront Slps 29, Chicago-40min, 2+ Ngt quotes NOT accurate, Please ask!, holiday rental in Chesterton
Lux Beachfront Slps 29, Chicago-40min, 2+ Ngt quotes NOT accurate, Please ask!, holiday rental in Chesterton

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

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 27
Match: Sleeps
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MODERN GEM, CLOSE TO DOWNTOWN VALPO AND VU, DUNES AND BEACHES, holiday rental in Chesterton
MODERN GEM, CLOSE TO DOWNTOWN VALPO AND VU, DUNES AND BEACHES, holiday rental in Chesterton
MODERN GEM, CLOSE TO DOWNTOWN VALPO AND VU, DUNES AND BEACHES, holiday rental in Chesterton

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

Holiday Rental House
3 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, holiday rental in Chesterton
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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Beautiful  apt next to Lighthouse Outlet Mall, holiday rental in Chesterton
Beautiful  apt next to Lighthouse Outlet Mall, holiday rental in Chesterton
Beautiful  apt next to Lighthouse Outlet Mall, holiday rental in Chesterton

Beautiful apt next to Lighthouse Outlet Mall

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

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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!, holiday rental in Chesterton
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!

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Two-Bedroom Apartment by Lighthouse Outlet Mall, holiday rental in Chesterton
Two-Bedroom Apartment by Lighthouse Outlet Mall, holiday rental in Chesterton
Two-Bedroom Apartment by Lighthouse Outlet Mall, holiday rental in Chesterton

Two-Bedroom Apartment by Lighthouse Outlet Mall

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Studio Apt with full kitchen next to The Lighthouse Outlet Mall in Town area, holiday rental in Chesterton
Studio Apt with full kitchen next to The Lighthouse Outlet Mall in Town area, holiday rental in Chesterton
Studio Apt with full kitchen next to The Lighthouse Outlet Mall in Town area, holiday 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
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Your family adventure awaits! Private Kayak Launch New for 2020!, holiday rental in Chesterton
Your family adventure awaits! Private Kayak Launch New for 2020!, holiday rental in Chesterton
Your family adventure awaits! Private Kayak Launch New for 2020!, holiday rental in Chesterton

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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, holiday rental in Chesterton
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

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

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

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 26
Match: Sleeps
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Studio apt. across from Lighthouse Outlet Mall, holiday rental in Chesterton
Studio apt. across from Lighthouse Outlet Mall, holiday rental in Chesterton
Studio apt. across from Lighthouse Outlet Mall, holiday rental in Chesterton

Studio apt. across from Lighthouse Outlet Mall

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

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

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

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
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, holiday rental in Chesterton
Miller Beach and Indiana Dunes National Park Vacation House, holiday rental in Chesterton

Miller Beach and Indiana Dunes National Park Vacation House

Holiday Rental House
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!, holiday rental in Chesterton
Ideal Family Getaway Home! 2bed 2bath sleeps 6, golf cart included!, holiday rental in Chesterton
Ideal Family Getaway Home! 2bed 2bath sleeps 6, golf cart included!, holiday rental in Chesterton

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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!, holiday rental in Chesterton
NEW! Stylish Home w/ Elevated Deck, Walk to Beach!, holiday rental in Chesterton

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

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Indiana Dunes Beach Getaway Home, holiday rental in Chesterton
Indiana Dunes Beach Getaway Home, holiday rental in Chesterton
Indiana Dunes Beach Getaway Home, holiday rental in Chesterton

Indiana Dunes Beach Getaway Home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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DunesWalk Inn - Vacation Rental, holiday rental in Chesterton
DunesWalk Inn - Vacation Rental, holiday rental in Chesterton
DunesWalk Inn - Vacation Rental, holiday rental in Chesterton

DunesWalk Inn - Vacation Rental

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

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Prime Lake Michigan Beach House - Indiana Dunes, holiday rental in Chesterton
Prime Lake Michigan Beach House - Indiana Dunes, holiday rental in Chesterton
Prime Lake Michigan Beach House - Indiana Dunes, holiday rental in Chesterton

Prime Lake Michigan Beach House - Indiana Dunes

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Beach front property with sunset view., holiday rental in Chesterton
Beach front property with sunset view., holiday rental in Chesterton
Beach front property with sunset view., holiday rental in Chesterton

Beach front property with sunset view.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Miller Beach - Indiana Dunes Family Getaway, holiday rental in Chesterton
Miller Beach - Indiana Dunes Family Getaway, holiday rental in Chesterton
Miller Beach - Indiana Dunes Family Getaway, holiday rental in Chesterton

Miller Beach - Indiana Dunes Family Getaway

Holiday Rental House
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, holiday rental in Chesterton
LUXURY BEACH HOUSE IN DUNES NATIONAL PARK with 40ft POOL, GARDEN & OPTIONAL BOAT, holiday rental in Chesterton
LUXURY BEACH HOUSE IN DUNES NATIONAL PARK with 40ft POOL, GARDEN & OPTIONAL BOAT, holiday rental in Chesterton

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The Eagles Nest, holiday rental in Chesterton
The Eagles Nest, holiday rental in Chesterton
The Eagles Nest, holiday rental in Chesterton

The Eagles Nest

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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