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Vacation rentals in Chesterton

Vacation 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.

  • The "Pool Barn" near Indiana Dunes & Lake Michigan
    SUPERHOSTEntire guest house · 12 guests · 6 beds · 1 bathroom
    The "Pool Barn" near Indiana Dunes & Lake Michigan

    POOL & HOT TUB open! More than a place to sleep! Only 5 minutes to beaches of Indiana Dunes on Lake Michigan. Dunes National Park & hiking along the Little Calumet River only 1 block away. Plenty to do at our space too! Air hockey, billiards, ping-pong, darts, basketball shot, foosball, & board games! Comfy beds & full kitchen! Enjoy the campfire, grill, & playground too. Pool heated 2020 May 22-Oct 4. Sun, swim, play, relax & volleyball. Please read House Rules prior to booking.

    What guests are saying:

    “We had another great vacation at the Pool Barn! This is our second year and we hope to make it a yearly event. The pool is warm, the Pool Barn has fun games, and the location so close to the beach cannot be beat. Don and Kim's whole family are present, available, and incredibly hospitable. Highly recommend!”

  • "myhathouse" detached studio downtown Chesterton
    SUPERHOSTEntire guest house · 4 guests · 1 bed · 1 bathroom
    "myhathouse" detached studio downtown Chesterton

    Vaulted 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

    What guests are saying:

    “The Hat House provided us a cozy, intimate setting for 4 adults to stay and spend time together. Everything was there that we could have wanted ; kitchen well stocked with cooking supplies, comfortable beds; outdoor fire pit with chairs surrounding, skylights to lighten the environment, particularly the one in the shower; very private feeling of entire house. We spent a good part of each day staying in Chesterton at the very nearby Indiana Dunes National Park where the hiking was wonderful and the vistas fantastic! We are thankful we found such a great place to stay”

  • Nice private room in country house
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bathroom
    Nice private room in country house

    Private room in newer home. Tv, Internet , private bath and use of kitchen, w queen sized bed, with us of kitchen, outdoor grill etc.

    What guests are saying:

    “Terry is very friendly and has a very clean, comfortable place! The bathroom is spacious and well-equipped, and the bedroom is convenient and comfortable. He provides anything you could possibly need and has great local tips!”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chesterton holiday rentals

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

Other great holiday rentals in Chesterton

Home away from home.
Entire house
Home away from home.
Price:€98 / night
Private Guest House, in Gated Nudist Resort.
SUPERHOSTEntire guest house
Private Guest House, in Gated Nudist Resort.
Price:€69 / night
Private 1 bd apt close to lake & local attractions
SUPERHOSTEntire flat
Private 1 bd apt close to lake & local attractions
Price:€73 / night
Tryon Country Retreat
SUPERHOSTEntire apartment
Tryon Country Retreat
Price:€109 / night
Sweet Home in Chesterton
SUPERHOSTEntire house
Sweet Home in Chesterton
Price:€124 / night
Cozy Bungalow, centrally located, 3 miles to beach
SUPERHOSTEntire house
Cozy Bungalow, centrally located, 3 miles to beach
Price:€106 / night
Private basement with kitchen bathroom and theater
SUPERHOSTEntire house
Private basement with kitchen bathroom and theater
Price:€39 / night
Le Chateau de Chien King
A Stay  Here Saves Dogs
SUPERHOSTPrivate room
Le Chateau de Chien King A Stay Here Saves Dogs
Price:€53 / night
Duneland Digs Beyond the Beach
SUPERHOSTEntire guest house
Duneland Digs Beyond the Beach
Price:€98 / night
Nature's resting place
SUPERHOSTEntire cabin
Nature's resting place
Price:€116 / night
2 bedroom apartment, separate entrance
SUPERHOSTEntire flat
2 bedroom apartment, separate entrance
Price:€67 / night
Fully Furnished Apt In Prime Valparaiso Location
SUPERHOSTEntire flat
Fully Furnished Apt In Prime Valparaiso Location
Price:€70 / night
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