Compare Chesterton Cottage Rentals

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Featured Chesterton Cottages

Cozy New Buffalo cottage with hot tub & fire pit. Short walk to downtown!

Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills. Other amenities at this family-friendly cottage include a water dispenser and a garden.

Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!

$503 nightly

$503 total

Nov 9 - Nov 10

Total with taxes and fees

Guests of this cottage enjoy features like a gym, a hot tub, and laundry facilities. Additional amenities include a water dispenser, barbecue grills, and a garden.

Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk

$376 nightly

$421 total

Nov 8 - Nov 9

Total with taxes and fees

At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills.

Spacious 3BR House With Firepit & Grill, Near Beach

$339 nightly

$357 total

Nov 16 - Nov 17

Total with taxes and fees

At this cottage, guests have access to barbecue grills.

Brand New Cottage Walkable to All Downtown Michigan City & Beach!

$251 nightly

$281 total

Nov 20 - Nov 21

Total with taxes and fees

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.

Beachglass Cottage - Family Friendly Kids and Pets

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.

The Hideaway House - Private, Peaceful, Cozy

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

Grand Beach Getaway – Hot Tub, Fire Pit & walk to the Lake | Weekend Restoration

Guests staying at this cottage enjoy a water park, a hot tub, and laundry facilities. This smoke-free cottage also has barbecue grills.

Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach

Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills.

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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

Spring House Inn

303 N Mineral Springs Rd, Chesterton, IN

$116 total

per night

Nov 9 - Nov 10

8.8/10 Excellent! (1,046 reviews)

Best Western Indian Oak

558 Indian Boundary Road, Chesterton, IN

$105 total

per night

Nov 13 - Nov 14

8.4/10 Very Good! (1,011 reviews)

Comfort Inn & Suites Porter near Indiana Dunes

1800 West US Highway 20, Chesterton, IN

$106 total

per night

Dec 7 - Dec 8

8/10 Very Good! (1,001 reviews)

Cottages

Book a cottage in Chesterton
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Chesterton. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Chesterton better.

Cottage apartments in Chesterton range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Chesterton
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Chesterton and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Chesterton cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Chesterton. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Chesterton Cottages essential information

Accommodation	92 Cottages
Lowest Price	$105
Highest Price	$503
Popular accommodation	Cozy New Buffalo cottage with hot tub & fire pit. Short walk to downtown!, Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!, Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk, Spacious 3BR House With Firepit & Grill, Near Beach, Brand New Cottage Walkable to All Downtown Michigan City & Beach!, Beachglass Cottage - Family Friendly Kids and Pets, The Hideaway House - Private, Peaceful, Cozy, Grand Beach Getaway – Hot Tub, Fire Pit & walk to the Lake \| Weekend Restoration, Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach