Holiday Rentals in Chesterton
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Holiday Rentals in Chesterton

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

July Sale!!!! 200/night Must book 3 nights to get this special price.

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly

The Neighborhood Hotel - Grand Beach

Lakefront Home - Sunroom, Deck, Grill & Lake View

Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Uptown Penthouse on Pine: By Lake Michigan, Shopping & Casino!

View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

Cozy 2 Bedroom Home Near Lake Michigan & Downtown

Cozy 2-bedroom condo in New Buffalo with indoor/outdoor pools

Walk to Lake Michigan Beach from Cottage in the Woods - *Seaside Fired Smores*

Steps from the beach! Pet friendly. Awesome amenities and great location.

5BR 3.5BA Dune Side Home w/ Short Walk to the BEACH! NEW LISTING - Built in 2022

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
Other types of properties in Chesterton you may be interested in

Best Western Indian Oak
Holiday Accommodation Chesterton
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Chesterton are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Chesterton itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Chesterton holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Chesterton, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Chesterton with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
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