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Chesterton vacation rentals

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Top-rated vacation rentals in Chesterton

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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
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
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

Stay near Chesterton's top sights

Photo of Indiana Dunes National Lakeshore Visitor Center
Indiana Dunes National Lakeshore Visitor Center12 locals recommend
Photo of Wagner's Ribs
Wagner's Ribs19 locals recommend
Photo of Jewel-Osco
Jewel-Osco12 locals recommend
Photo of Coffee Creek Watershed Preserve
Coffee Creek Watershed Preserve12 locals recommend
Photo of Strack & Van Til
Strack & Van Til7 locals recommend
Photo of Octave Grill
Octave Grill18 locals recommend

Chesterton cabin rentals

Cabin in Michigan City
Nature's resting place
$136 per night
Cabin in Portage
Cozy Log Cabin Near Indiana Dunes & Lake Michigan!
$199 per night
Cabin in Michigan City
Forest retreat The Pocket House
$158 per night
Cabin in Griffith
Beautiful Rustic Cabin for Two!
$74 per night
Cabin in Michiana
Romantic Getaway in the Dunes for a Couple—Hüüsli
$263 per night
Cabin in Valparaiso
Rustic Cozy 'Bear Den' in Gated Nudist Community
$99 per night
Cabin in Union Pier
McComb's Cabin, Union Pier, MI
$158 per night
Cabin in Grovertown
Cozy Cabin at Coppertop Barn
$117 per night
Cabin in Michiana Shores
Cozy Cabin on the grounds of a riding stables
$148 per night
Cabin in Michiana
Steps to the beach at cute cabin 1hr from Chicago
$300 per night
Cabin in Michiana Shores
New Buffalo - Michiana Romantic Getaway Cabin -
$300 per night
Cabin in Three Oaks
Architect Hideaway, Michigan Woods Retreat
$248 per night
  1. Airbnb
  2. United States
  3. Indiana
  4. Porter County
  5. Chesterton