Chesterton Holiday Rentals
Holiday Rentals in Chesterton
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Blue Birdhouse by the Beach
The Neighborhood Hotel - Grand Beach
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Dunes Escape - Minutes from Indiana Dunes National Park
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
Treehouse Bungalow- Quaint and Cozy Getaway!
Hot tub and Golf Cart 6 bedrooms plus coach house. July 26th -Aug 2nd, 2024 open
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
Cozy Michigan City Beach Cottage #2
The Victorian Carriage House. Built in 1880, this restored cottage is a charmer.
Walk Downtown, Huge Hot tub, Coffee on the Porch!
Newly Renovated City Escape with a private hot tub
This 3 bedroom, 2 bathroom home is in a scenic area but closes to Indiana Dunes National Park.
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
Beach, casino, pet-friendly cottage
Walking distance to beach, 2 Bedroom, Pet Friendly
7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!
Other types of properties in Chesterton you may be interested in
Best Western Indian Oak
Spring House Inn
Waterbird Lakeside Inn
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chesterton holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Chesterton. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chesterton. Seeing all the best attractions is bound to make you fall in love with Chesterton. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chesterton short-term rentals, that won’t be hard to do.
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