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Vacation rentals in Chesterton

Find and book unique accommodations on Airbnb

Top-rated vacation 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 bath

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.

The Lake Escape -Cozy Lakefront Cottage Valparaiso
SUPERHOST
Entire cottage · 8 guests · 5 beds · 1.5 baths

The Lake Escape -Cozy Lakefront Cottage ValparaisoEscape the everyday with a relaxing stay at this cozy cottage located on Flint Lake! Hot tub, pontoon boat, sauna, fire pit, gas fireplace, tv, lake front, canoe, kayak, grill and more. This charming property is lake front with a small 50ft beach area and dock. Use of 2018 Sylvan pontoon boat, canoe, and kayak are included. You will love the lake life.

"myhathouse" detached studio downtown Chesterton
SUPERHOST
Entire guesthouse · 4 guests · 1 bed · 1 bath

"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

Vacation rentals for every style

Get the amount of space that is right for you.

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  • Hotels
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Popular amenities for Chesterton vacation rentals

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

Other great vacation rentals in Chesterton

SUPERHOST
  1. Entire residential home
  2. Porter
Modern Indiana Beach Home Near Lake Michigan
  1. Entire guesthouse
  2. Chesterton
Bro’s Place
  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
Flint Lake Cottage.
  1. Hotel room
  2. Porter
King Bed with Balcony
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 guesthouse
  2. Porter
The "Pool Barn" near Indiana Dunes & Lake Michigan

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