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Holiday rentals in Chesterton

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chesterton

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

Hotel Whiskey
SUPERHOST
Entire residential home · 4 guests · 2 beds · 1 bathroom

Hotel WhiskeyFully remodeled and tastefully decorated two bedroom home for short or long term stays. Office space for work travelers. Pet friendly with secure fenced in back yard. Walking distance from downtown with quaint shops, wine bar, craft beer bar, restaurants and bike trails. Whether you're in town for work, visiting family or just looking for a weekend getaway, this house and location are perfect for short or long term stays.

Country Setting Guest House
Entire guest house · 4 guests · 2 beds · 1 bathroom

Country Setting Guest HouseWelcome 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

"myhathouse" detached studio downtown Chesterton
SUPERHOST
Entire guest house · 4 guests · 1 bed · 1 bathroom

"myhathouse" detached studio downtown ChestertonVaulted skylights allow natural light. Ksize bed. Futon opens into a bed. (DEEP cleaned to AirBnb COVID-19 disinfectant standards) Fully stocked kitchen, sm. bathroom w/ shower. Parking ft. of house, 1.5 M from Lake Michigan Shoreline, 2 blocks to 15th St. entry to Prairie-Dune Trail. European Market (May -Oct) each Saturday downtown. Fall season drives along U.S. HW 12 & 20 for foliage Winter day hikes, x-county skis trail, shopping trips to the Michigan City Outlet mall

Holiday rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Chesterton holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chesterton

SUPERHOST
  1. Entire residential home
  2. Porter
Modern Indiana Beach Home Near Lake Michigan
  1. Entire residential home
  2. Porter
Indiana Dunes Retreat
SUPERHOST
  1. Farm stay
  2. Valparaiso
The Good Farm of Valpo: 1853 farmhouse on 44 acres
SUPERHOST
  1. Entire residential home
  2. Beverly Shores
Secluded Modern Retreat Near Beach - "Sandlot"
SUPERHOST
  1. Entire residential home
  2. Portage
Poppy's Place - Family Ranch
SUPERHOST
  1. Entire residential home
  2. Chesterton
Downtown Chesterton Cottage
SUPERHOST
  1. Entire cottage
  2. Valparaiso
The Lake Escape -Cozy Lakefront Cottage Valparaiso
SUPERHOST
  1. Entire cottage
  2. Valparaiso
Flint Lake Cottage.
SUPERHOST
  1. Entire residential home
  2. Valparaiso
Lonely Pine Guest House: A Peaceful, Wooded Stay
SUPERHOST
  1. Entire guest suite
  2. Porter
The Porter House
SUPERHOST
  1. Entire guest house
  2. Porter
The "Pool Barn" near Indiana Dunes & Lake Michigan
SUPERHOST
  1. Private room
  2. Portage
Urban living close to big city, beach, malls, yoga

Nearby destinations