Book Holiday Homes in Chesterton
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Featured Holiday Homes in Chesterton
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
Cozy and Private Home with Fireplace on Wooded Lot Near Lake Michigan Beaches
cozy home with hot tub next to downtown Valparaiso
Nestled just behind Marquette Park. 5 minute walk to beach.
Roomy Retreat-Family & Friends|2 King B|Game Room| | Valpo University | Dunes
Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly
Walk to the Beach from Beachy Farmhouse - Lake Michigan & Hot Tub. Pet-Friendly!
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
Chesterton Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chesterton vacation homes are the perfect way for you to wing it.
Holiday houses in Chesterton let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chesterton in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chesterton adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chesterton with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chesterton vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Chesterton Holiday Homes essential information
Accommodation | 611 Holiday Homes |
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Lowest Price | NZ$168 |
Highest Price | NZ$937 |
Popular accommodation | Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!, Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!, Cozy and Private Home with Fireplace on Wooded Lot Near Lake Michigan Beaches , cozy home with hot tub next to downtown Valparaiso, Nestled just behind Marquette Park. 5 minute walk to beach., Roomy Retreat-Family & Friends|2 King B|Game Room| | Valpo University | Dunes, Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly, Walk to the Beach from Beachy Farmhouse - Lake Michigan & Hot Tub. Pet-Friendly!, Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park |
More accommodations in Chesterton
Top trending hotels in Chesterton
Spring House Inn
Best Western Indian Oak
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Hilton Garden Inn Chesterton
More ways to explore Chesterton
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.