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Holiday Rentals with Pools 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!
2 bedrooms
1 bathroom
Sleeps 6
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5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool
5 bedrooms
3 bathrooms
Sleeps 20
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NEW! Quaint Chesterton Home in Walkable Location!
4 bedrooms
2 bathrooms
Sleeps 7
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Classic Roomy Cottage. Best walk-to-everything location.
3 bedrooms
2 bathrooms
Sleeps 10
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Spacious, Fun and Family Friendly Beach Home
4 bedrooms
3 bathrooms
Sleeps 14
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Artistic Loft close to Lake Michigan beaches, craft breweries & outlet shopping
1 bedroom
1 bathroom
Sleeps 4
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Beautiful New Home! Book Now, Summer is filling up fast!!
4 bedrooms
3 bathrooms
Sleeps 10
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Dune Fine Is A Brand New Family Friendly Home Right On The Beach
4 bedrooms
3 bathrooms
Sleeps 10
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Indiana Dunes Beach Rental
2 bedrooms
1 bathroom
Sleeps 5
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Family Home Near Downtown Valpo & University
3 bedrooms
1 bathroom
Sleeps 7
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Beautiful Beach Cottage - 205 California Ave
3 bedrooms
3 bathrooms
Sleeps 12
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'How You Dune?'- Lake Michigan Beach House Perfect For Large Groups!
7 bedrooms
4 bathrooms
Sleeps 15
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Porter Beach Vacation Getway! Lake Michigan Beachside Home - Newly Remodeled
2 bedrooms
1 bathroom
Sleeps 8
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Rare Private Pool w/in 1.5 Blocks to the Beach!
5 bedrooms
2 bathrooms
Sleeps 11
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Cozy and Charming Beach Getaway on Lovely Lake Michigan
1 bedroom
1 bathroom
Sleeps 4
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Charming Beach Front Cottages
3 bedrooms
1 bathroom
Sleeps 6
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New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo
2 bedrooms
1 bathroom
Sleeps 6
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Beautiful apt next to Lighthouse Outlet Mall
1 bedroom
1 bathroom
Sleeps 3
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Vintage Lake Michigan Beach Cottage: 4br+loft,3ba-Sleeps 17
4 bedrooms
3 bathrooms
Sleeps 18
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Vintage Cottage with Covid Protocols
4 bedrooms
2 bathrooms
Sleeps 8
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Casa Blanca in Miller Beach
6 bedrooms
5 bathrooms
Sleeps 17
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New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo
2 bedrooms
1 bathroom
Sleeps 6
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Lighthouse apt. Great location right by Lighthouse Outlet Mall See the Sale!
1 bedroom
1 bathroom
Sleeps 3
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Walk to Lake Michigan Beach! Sleeps 12 - 14!
5 bedrooms
2 bathrooms
Sleeps 14
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Two-Bedroom Apartment by Lighthouse Outlet Mall
2 bedrooms
1 bathroom
Sleeps 4
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Lovely Lake Michigan Beach Rental
4 bedrooms
2 bathrooms
Sleeps 10
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Big Cozy House In The Dunes (5bed/3.5bath plus loft) - Nested In Wooded Hillside
6 bedrooms
4 bathrooms
Sleeps 14
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Stunning Home (Sleeps 16) Hot Tub, Firepit, Large Yard -45 min to Notre Dame
5 bedrooms
4 bathrooms
Sleeps 16
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Nice beach house
3 bedrooms
2 bathrooms
Sleeps 6
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Studio apt. across from Lighthouse Outlet Mall
1 bedroom
1 bathroom
Sleeps 2
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Lake House on beach path, sleeps 12!
2 bedrooms
3 bathrooms
Sleeps 12
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5BD 2BA Cottage walking distance to Sheridan Beach & 30 min drive to Norte Dame
5 bedrooms
2 bathrooms
Sleeps 12
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Amazing Views From Beachfront Unit In the Heart of the Indiana Dunes
2 bedrooms
1 bathroom
Sleeps 5
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Brand New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo
4 bedrooms
2 bathrooms
Sleeps 12
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Minutes to beach, businesses and train!
2 bedrooms
1 bathroom
Sleeps 6
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A great time for a weekend get away!!!
3 bedrooms
2 bathrooms
Sleeps 8
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CONDO FOR RENT IN FLORIDA
1 bedroom
2 bathrooms
Sleeps 4
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Lake Michigan Sheridan Beach w/private off street parking + Billiard Table
3 bedrooms
2 bathrooms
Sleeps 12
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DunesWalk Inn - Vacation Rental
5 bedrooms
5 bathrooms
Sleeps 19
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Dune our Thing- 1 block to beach with private parking and lake views!
6 bedrooms
6 bathrooms
Sleeps 16
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ON THE BEACH
3 bedrooms
2 bathrooms
Sleeps 5
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Beach Cottage* Walk 800 ft. to Lake Michigan's Sheridan Beach* NEW LISTING
2 bedrooms
1 bathroom
Sleeps 5
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NEW LISTING! Lake Michigan Views | Multi-Level | Sleeps 6 | 2 Car Garage
3 bedrooms
2 bathrooms
Sleeps 6
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Miller Beach and Indiana Dunes National Park Vacation House
3 bedrooms
2 bathrooms
Sleeps 11
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NEW! Stylish Home w/ Elevated Deck, Walk to Beach!
5 bedrooms
3 bathrooms
Sleeps 10
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Lakefront Family Retreat w/ Grill: Steps to Beach!
4 bedrooms
3 bathrooms
Sleeps 8
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Sunflower Cottage by the beach, parks, zoo and more.
3 bedrooms
1 bathroom
Sleeps 7
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NEW! Well-Appointed Gary Home Few Blocks to Beach!
4 bedrooms
2 bathrooms
Sleeps 10
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Creature Comforts at Catalpa
3 bedrooms
2 bathrooms
Sleeps 7
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It's the Wright Farm
1 bedroom
1 bathroom
Sleeps 2
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