Chesterton Cottages

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

Cottages in Chesterton

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

New Buffalo MI

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

Pool

Hot Tub

Spacious 3BR House With Firepit & Grill, Near Beach

North Hamilton Street 234 Gary IN

$325 nightly

$340 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

With a stay at this cottage in Gary (Miller Beach), you'll be within a 5-minute drive of Lake Michigan and Indiana Dunes National Park.

Kitchen

Pet friendly

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

Michigan City IN

$263 nightly

$295 total

Dec 7 - Dec 8

Total with taxes and fees

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

Kitchen

Washer

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

New Buffalo MI

Located in New Buffalo, this cottage is within a 15-minute drive of Lake Michigan and Four Winds Casino New Buffalo.

Hot Tub

Kitchen

Beachglass Cottage - Family Friendly Kids and Pets

Grand Beach MI

With a stay at this cottage in New Buffalo, you'll be a 2-minute drive from Lake Michigan and 9 minutes from Blue Chip Casino.

Kitchen

Washer

Simple Cottage Set in the Woods by Lake Michigan

New Buffalo MI

Located in New Buffalo, this cottage is within a 15-minute drive of Lake Michigan and Blue Chip Casino.

Kitchen

Washer

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

Michigan City IN

$372 nightly

$417 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

When you stay at this cottage in Michigan City, you'll be near the beach, a 2-minute drive from Lake Michigan and 5 minutes from Blue Chip Casino.

Pool

Kitchen

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

New Buffalo MI

With a stay at this cottage in New Buffalo, you'll be a 4-minute drive from Lake Michigan and 9 minutes from Blue Chip Casino.

Kitchen

Washer

The Hideaway House - Private, Peaceful, Cozy

Grand Beach MI

With a stay at this cottage in New Buffalo, you'll be a 2-minute drive from Lake Michigan and 9 minutes from Blue Chip Casino.

Kitchen

Washer

Steps to everything! The Cape Codder at Beachwalk Resort w/ Water Views

Michigan City IN

With a stay at this cottage in Michigan City, you'll be on the waterfront, a 5-minute walk from Lake Michigan and a 4-minute drive from Blue Chip Casino.

Pool

Kitchen

Treehouse Bungalow- Quaint and Cozy Getaway!

Michigan City IN

$382 nightly

$428 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

With a stay at this cottage, you'll be centrally located in Michigan City, a 5-minute drive from Blue Chip Casino and 6 minutes from Lake Michigan.

Kitchen

Washer

Blue Haven Cottage - New Buffalo Beach, near Wineries & Breweries

New Buffalo MI

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

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.