Chesterton vacation rentals

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Top-rated vacation rentals in Chesterton

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Home in Chesterton

Downtown Chesterton Cottage

Charming downtown house with a front porch, back deck & covered patio. Beautifully decorated with a small fenced in backyard. Minutes from the Indiana Dunes National Park and beaches. Near the South Shore Commuter train if you wish to visit Chicago without the drive and expense of parking. We are across from an active train track so if you like trains you can watch them from the front porch. Walk to restaurants, wineries and beer pubs. European market on Saturdays from May to end of October.

$181 per night

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Guest suite in Chesterton

Private Downtown Apt w/Jet Bath near Indiana Dunes

Downtown Chesterton private apartment. Walk to parks, dining, shopping, taverns, winery, European market, & more. Only 3 miles from sand beaches & hiking trails at Indiana Dunes State Park & Indiana Dunes National Park. Apt has living, dining, full kitchen, large bedroom with King Size bed, large jet bath & fireplace, & 60" smart tv. Living room has L shaped couch that sleeps 2, & a 60" smart tv. Spare Queen mattress available by request. Glider & gas grill outside too. No cleaning fee!

$115 per night

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Guesthouse in Chesterton

Bro’s Place

Welcome if you like country life Bro’s place is the place to be...watching the sheep, chickens and wildlife on you back deck making dinner on the grill with a full kitchen. Pick your own veggies outside the back door when in season. You will find a welcome basket with snacks, wine and homemade soap in bathroom fresh eggs from our chickens when available if your planning to visit our Beautiful Indiana Dunes you’ll find everything you need..chairs, towels, cooler Queen size sofa sleeper

$99 per night

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