Chesterton Vacation Homes

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Featured Vacation Homes in Chesterton

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Chesterton

    Waterbird Lakeside Inn

    Waterbird Lakeside Inn

    556 Indian Boundary Road, Chesterton, IN
    $90 nightly
    The price is $101 total per night from Nov 2 to Nov 3
    $101 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8/10 Very Good! (953 reviews)
    Spring House Inn

    Spring House Inn

    303 N Mineral Springs Rd, Chesterton, IN
    $103 nightly
    The price is $116 total per night from Oct 5 to Oct 6
    $116 total
    Oct 5 - Oct 6
    Total with taxes and fees
    8.8/10 Excellent! (1,033 reviews)
    Best Western Indian Oak

    Best Western Indian Oak

    558 Indian Boundary Road, Chesterton, IN
    $89 nightly
    The price is $100 total per night from Nov 2 to Nov 3
    $100 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.4/10 Very Good! (1,017 reviews)

Chesterton Vacation Homes

Book vacation homes in Chesterton
Next time you take a group getaway top Chesterton, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Chesterton vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Chesterton vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Chesterton; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Chesterton rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Chesterton is sure to be a winner.

Chesterton Vacation Homes essential information

Accommodation
784 Vacation Homes
Lowest Price
$100
Highest Price
$116
Popular accommodation
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven., Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart, Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!, "The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room, Amazing Lake Views, Beach Access, Hot Tub, Fire Pit, Screened Porch & Game Room, Sweet Stay By-The-Lake in Michigan City with AC, WiFi, Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna, Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!, Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

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