Compare Chesterton Guest House Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Guest Houses in Chesterton

Luxury Guesthouse in private wooded setting in Grand Beach New Buffalo

$398

includes taxes & fees

$398 per night

Dec 23 - Dec 24

At this guesthouse, guests have access to a garden.

Chesterton “Golf View Estate” Midwest Great Lake Beaches & Trails Of The Dunes!

Guests staying at this guesthouse have access to a garden and barbecue grills.

At this guesthouse, guests have access to an outdoor pool and barbecue grills. Helpful staff is there to provide concierge services, as well as offer insight about the area.

Don't see what you're looking for?

See all available properties in Chesterton

View all properties

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

$100

includes taxes & fees

$89 per night

Dec 23 - Dec 24

8.8/10 Excellent! (1,000 reviews)

Best Western Indian Oak

558 Indian Boundary Road, Chesterton, IN

$95

includes taxes & fees

$85 per night

Dec 29 - Dec 30

8.4/10 Very Good! (1,001 reviews)

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

Porter

$293

includes taxes & fees

$262 per night

Jan 6 - Jan 7, 2025

10/10 Exceptional! (72 reviews)

Chesterton Guest Houses essential information

Accommodation	4 Guest Houses
Lowest Price	$95
Highest Price	$398
Popular accommodation	Luxury Guesthouse in private wooded setting in Grand Beach New Buffalo, Chesterton “Golf View Estate” Midwest Great Lake Beaches & Trails Of The Dunes!, Couples Getaway! Studio w/ Queen