Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Compare Chesterton Cottage 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 Chesterton Cottages

Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5

Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5

New Buffalo, MI
Guests staying at this cottage enjoy a water park, a garden, and barbecue grills.
Beach Cottage Walk 800 ft. to Lake Michigan's Sheridan Beach NEW Listing

Beach Cottage Walk 800 ft. to Lake Michigan's Sheridan Beach NEW Listing

Michigan City, IN
This cottage is a smoke-free cottage.
Lake Michigan Beach Cottages

Lake Michigan Beach Cottages

4 out of 5
1402 Lake Shore, Michigan City, IN
Lake Michigan Beach Cottages is a smoke-free property.
Vintage Lake Michigan Beach Cottage: 4br+loft,3ba-sleeps 17

Vintage Lake Michigan Beach Cottage: 4br+loft,3ba-sleeps 17

Michigan City, IN
This cottage features a water park and barbecue grills.
Outdoor Living Steps From the Beach With Great Lake Views! Great Location

Outdoor Living Steps From the Beach With Great Lake Views! Great Location

Michigan City, IN
At this cottage, guests have access to barbecue grills.
Spacious, Fun and Family Friendly Beach Home

Spacious, Fun and Family Friendly Beach Home

Gary, IN
Guests staying at this cottage enjoy features like a water park.
3BR Beach Cottage Steps to the Sandy Shores of Lake Michigan's Sheridan Beach

3BR Beach Cottage Steps to the Sandy Shores of Lake Michigan's Sheridan Beach

Michigan City, IN
This cottage is a smoke-free cottage.
Bright & Airy Cottage w/ Deck & View, Walk to Lake

Bright & Airy Cottage w/ Deck & View, Walk to Lake

Michigan City, IN
At this cottage, guests have access to features like an arcade/game room. This family-friendly cottage also has a garden.
New! Home, < 2 Mi to New Buffalo Beach & Boat Ramp

New! Home, < 2 Mi to New Buffalo Beach & Boat Ramp

New Buffalo, MI
At this cottage, guests have access to a garden.
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

    Best Western Indian Oak

    Best Western Indian Oak

    558 Indian Boundary Road, Chesterton, IN
    The price is $102 per night from Jun 27 to Jun 27
    4/5Very Good! (53 reviews)
    Best Western Indian Oak
    Waterbird Lakeside Inn

    Waterbird Lakeside Inn

    556 Indian Boundary Road, Chesterton, IN
    The price is $90 per night from Jun 14 to Jun 14
    3.6/5Good! (11 reviews)
    Waterbird Lakeside Inn
    Hilton Garden Inn Chesterton

    Hilton Garden Inn Chesterton

    501 Gateway Boulevard, Chesterton, IN
    The price is $116 per night from Jul 11 to Jul 11
    4.2/5Very Good! (36 reviews)
    Hilton Garden Inn Chesterton