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Holiday Homes in Chesterton

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Bedrooms

Bathrooms

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5 km
23 rentals in Chesterton.
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes, holiday rental in Chesterton
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes, holiday rental in Chesterton
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes, holiday rental in Chesterton

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Blue Birdhouse by the Beach, holiday rental in Chesterton
Blue Birdhouse by the Beach, holiday rental in Chesterton
Blue Birdhouse by the Beach, holiday rental in Chesterton

Blue Birdhouse by the Beach

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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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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Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago, holiday rental in Chesterton
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago, holiday rental in Chesterton
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago, holiday rental in Chesterton

Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes, holiday rental in Chesterton
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes, holiday rental in Chesterton
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes, holiday rental in Chesterton

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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NEW! Beautiful Riverfront Home on 10 Acres!, holiday rental in Chesterton
NEW! Beautiful Riverfront Home on 10 Acres!, holiday rental in Chesterton
NEW! Beautiful Riverfront Home on 10 Acres!, holiday rental in Chesterton

NEW! Beautiful Riverfront Home on 10 Acres!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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INDIANA DUNES/LAKE MICHIGAN/DOWNTOWN CHESTERTON, holiday rental in Chesterton
INDIANA DUNES/LAKE MICHIGAN/DOWNTOWN CHESTERTON, holiday rental in Chesterton
INDIANA DUNES/LAKE MICHIGAN/DOWNTOWN CHESTERTON, holiday rental in Chesterton

INDIANA DUNES/LAKE MICHIGAN/DOWNTOWN CHESTERTON

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to, holiday rental in Chesterton
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to, holiday rental in Chesterton
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to, holiday rental in Chesterton

Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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National Park Nature Lover's Paradise w/ access to Chicago and Beach, holiday rental in Chesterton
National Park Nature Lover's Paradise w/ access to Chicago and Beach, holiday rental in Chesterton
National Park Nature Lover's Paradise w/ access to Chicago and Beach, holiday rental in Chesterton

National Park Nature Lover's Paradise w/ access to Chicago and Beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Spacious 4 BR 10 mins to  Near Chicago Sleeps 12, holiday rental in Chesterton
Spacious 4 BR 10 mins to  Near Chicago Sleeps 12, holiday rental in Chesterton
Spacious 4 BR 10 mins to  Near Chicago Sleeps 12, holiday rental in Chesterton

Spacious 4 BR 10 mins to Near Chicago Sleeps 12

Holiday Rental House
4 bedrooms
0 bathrooms
Sleeps 12
Match: Sleeps
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Private Kayak Launch and Zip Line Near the Dunes, holiday rental in Chesterton
Private Kayak Launch and Zip Line Near the Dunes, holiday rental in Chesterton
Private Kayak Launch and Zip Line Near the Dunes, holiday rental in Chesterton

Private Kayak Launch and Zip Line Near the Dunes

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Chesterton Home: w/ Idyllic Location!, holiday rental in Chesterton
Charming Chesterton Home: w/ Idyllic Location!, holiday rental in Chesterton
Charming Chesterton Home: w/ Idyllic Location!, holiday rental in Chesterton

Charming Chesterton Home: w/ Idyllic Location!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cozy Abode ~ 3 Mi to Indiana Dunes Nat'l Park, holiday rental in Chesterton
Cozy Abode ~ 3 Mi to Indiana Dunes Nat'l Park, holiday rental in Chesterton
Cozy Abode ~ 3 Mi to Indiana Dunes Nat'l Park, holiday rental in Chesterton

Cozy Abode ~ 3 Mi to Indiana Dunes Nat'l Park

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Indiana State Park TownHouse 1100 feet Boho Style: Extended-short-term stays, holiday rental in Chesterton
Indiana State Park TownHouse 1100 feet Boho Style: Extended-short-term stays, holiday rental in Chesterton
Indiana State Park TownHouse 1100 feet Boho Style: Extended-short-term stays, holiday rental in Chesterton

Indiana State Park TownHouse 1100 feet Boho Style: Extended-short-term stays

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chesterton Charmer: Lower Unit, holiday rental in Chesterton
Chesterton Charmer: Lower Unit, holiday rental in Chesterton
Chesterton Charmer: Lower Unit, holiday rental in Chesterton

Chesterton Charmer: Lower Unit

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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2 miles from Dunes National Park. A Unique Boutique Hotel., holiday rental in Chesterton
2 miles from Dunes National Park. A Unique Boutique Hotel., holiday rental in Chesterton
2 miles from Dunes National Park. A Unique Boutique Hotel., holiday rental in Chesterton

2 miles from Dunes National Park. A Unique Boutique Hotel.

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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Roomy Retreat-Family & Friends|2 King B|Game Room| | Valpo University | Dunes, holiday rental in Chesterton
Roomy Retreat-Family & Friends|2 King B|Game Room| | Valpo University | Dunes, holiday rental in Chesterton
Roomy Retreat-Family & Friends|2 King B|Game Room| | Valpo University | Dunes, holiday rental in Chesterton

Roomy Retreat-Family & Friends|2 King B|Game Room| | Valpo University | Dunes

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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That 70’s Loft- Peace, Love and a Funky Stay!, holiday rental in Chesterton
That 70’s Loft- Peace, Love and a Funky Stay!, holiday rental in Chesterton
That 70’s Loft- Peace, Love and a Funky Stay!, holiday rental in Chesterton

That 70’s Loft- Peace, Love and a Funky Stay!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Quaint 40a farm! Cozy fireplace, Llama encounters, chef service, nearby, holiday rental in Chesterton
Quaint 40a farm! Cozy fireplace, Llama encounters, chef service, nearby, holiday rental in Chesterton
Quaint 40a farm! Cozy fireplace, Llama encounters, chef service, nearby, holiday rental in Chesterton

Quaint 40a farm! Cozy fireplace, Llama encounters, chef service, nearby

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Heart of Indiana Dunes National Park with Hot Tub, holiday rental in Chesterton
Heart of Indiana Dunes National Park with Hot Tub, holiday rental in Chesterton
Heart of Indiana Dunes National Park with Hot Tub, holiday rental in Chesterton

Heart of Indiana Dunes National Park with Hot Tub

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Chesterton Charmer: 2 Units in 1, holiday rental in Chesterton
Chesterton Charmer: 2 Units in 1, holiday rental in Chesterton
Chesterton Charmer: 2 Units in 1, holiday rental in Chesterton

Chesterton Charmer: 2 Units in 1

Condo/Apartment
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Chesterton Charmer: Upper Unit, holiday rental in Chesterton
Chesterton Charmer: Upper Unit, holiday rental in Chesterton
Chesterton Charmer: Upper Unit, holiday rental in Chesterton

Chesterton Charmer: Upper Unit

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Check-out
As seen on
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That 70’s Loft!- Peace, Love and A Funky Stay!, holiday rental in Chesterton
That 70’s Loft!- Peace, Love and A Funky Stay!, holiday rental in Chesterton
That 70’s Loft!- Peace, Love and A Funky Stay!, holiday rental in Chesterton

That 70’s Loft!- Peace, Love and A Funky Stay!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
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Showing results 1-23 of 23
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