Chesterton Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Chesterton hotels

Vacation Rentals in Chesterton

Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

Michigan City IN

When you stay at this vacation home in Michigan City, you'll be near the beach, within a 5-minute drive of Lake Michigan and Blue Chip Casino.

Pool

Kitchen

Steps from the beach! Pet friendly. Awesome amenities and great location.

Michigan City IN

With a stay at this vacation home in Michigan City, you'll be on the beach, steps from Lake Michigan and a 3-minute drive from Blue Chip Casino.

Kitchen

Washer

Walk to the beach! Great modern home with spring and early summer availability!

Michigan City IN

When you stay at this vacation home in Michigan City, you'll be on a lake, within a 15-minute walk of Lake Michigan and Blue Chip Casino.

Kitchen

Washer

'Stones Throw' Lakeside Home - Walk to Marina + Assoc Beach

New Buffalo MI

With a stay at this vacation home, you'll be centrally located in New Buffalo, a 1-minute drive from Lake Michigan and 13 minutes from Four Winds Casino New Buffalo.

Kitchen

Washer

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Michigan City IN

With a stay at this vacation home, you'll be centrally located in Michigan City, within a 5-minute drive of Indiana Dunes National Park and Blue Chip Casino.

Hot Tub

Kitchen

Gecko Cottage ... Walk to beach, pool, food, shopping - Clean, cozy, ahhh

New Buffalo MI

With a stay at this vacation home, you'll be centrally located in New Buffalo, a 3-minute drive from Lake Michigan and 11 minutes from Four Winds Casino New Buffalo.

Pool

Kitchen

1:00 pm Check-In & Out! - 1 mile to Dunes - Roomy-Sleeps 16 - 🎮Game Room Loft🏓

Porter IN

With a stay at this vacation home, you'll be centrally located in Chesterton, within a 5-minute drive of Indiana Dunes National Park and Indiana Dunes State Park.

Kitchen

Washer

Happy Hideaway: Downtown New Buffalo Cottage, Big Fenced Yard, Fire Pit

New Buffalo MI

With a stay at this vacation home in New Buffalo (Downtown New Buffalo), you'll be within a 15-minute drive of Lake Michigan and Four Winds Casino New Buffalo.

Kitchen

Washer

Comfortable 3BR Home-Prime Video, WiFi, Parking

Schererville IN

Located in Schererville, this vacation home is within a 10-minute drive of Westfield Southlake Mall and Methodist Hospitals Diabetes.

Pool

Kitchen

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

Michigan City IN

With a stay at this vacation home in Michigan City, you'll be within a 5-minute drive of Lake Michigan and Blue Chip Casino.

Pool

Kitchen

View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

Michigan City IN

$718 nightly

$804 total

Oct 5 - Oct 6

Total with taxes and fees

With a stay at this vacation home in Michigan City, you'll be on the waterfront, steps from Lake Michigan and a 4-minute drive from Blue Chip Casino.

Kitchen

Washer

Adorable cottage in the Michiana Shores area! Close to Lake Michigan and Dunes

Michigan City IN

With a stay at this vacation home, you'll be centrally located in Michigan City, a 2-minute drive from Lake Michigan and 8 minutes from Blue Chip Casino.

Kitchen

Washer

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.