Chesterton Guest Houses

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Guest Houses in Chesterton

Luxury Guesthouse in private wooded setting in Grand Beach New Buffalo

New Buffalo MI

$400 nightly

$400 total

Dec 6 - Dec 7

Total with taxes and fees

When you stay at this guesthouse in New Buffalo, you'll be on a lake, within a 15-minute drive of Lake Michigan and Blue Chip Casino.

Pet friendly

Air conditioning

Elyon Hall CoachHouse, Indiana Dunes Nat’l Park, 10 min hike to Beach

Miller Beach IN

Located in Gary (Miller Beach), this guesthouse is steps from Lake Michigan and a 3-minute drive from Indiana Dunes National Park.

Pet friendly

Free WiFi

Cozy Couples Retreat in Beachwalk Resort w/ Hot Tub

Michigan City IN

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

Pool

Air conditioning

Captain Whittaker Suite 2 bedroom, 2 baths

New Buffalo MI

With a stay at this guesthouse, you'll be centrally located in New Buffalo, a 2-minute drive from Lake Michigan and 11 minutes from Four Winds Casino New Buffalo.

Hot Tub

Free WiFi

Galien Room Suite King size with Jacuzzi

New Buffalo MI

With a stay at this guesthouse, you'll be centrally located in New Buffalo, a 2-minute drive from Lake Michigan and 11 minutes from Four Winds Casino New Buffalo.

Hot Tub

Free WiFi

Beacons' Nest – Valpo U, Downtown & Dunes

Valparaiso IN

$206 nightly

$231 total

Dec 7 - Dec 8

Total with taxes and fees

A stay at this guesthouse places you in the heart of Valparaiso, within a 5-minute drive of Chicago Street Theatre and Porter County Museum.

Pet friendly

Free WiFi

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

Chesterton IN

With a stay at this guesthouse in Chesterton, you'll be within a 10-minute drive of Indiana Dunes National Park and Portage Imagination Glen Park.

Free WiFi

Air conditioning

SS Post Boy Queen Suite with Jacuzzi

New Buffalo MI

With a stay at this guesthouse, you'll be centrally located in New Buffalo, a 2-minute drive from Lake Michigan and 11 minutes from Four Winds Casino New Buffalo.

Hot Tub

Free WiFi

Eber Knight Studio - King size with Jacuzzi

New Buffalo MI

$199 nightly

$213 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

With a stay at this guesthouse, you'll be centrally located in New Buffalo, a 2-minute drive from Lake Michigan and 11 minutes from Four Winds Casino New Buffalo.

Hot Tub

Free WiFi

Snug Harbor Suite - King with Jacuzzi

New Buffalo MI

With a stay at this guesthouse, you'll be centrally located in New Buffalo, a 2-minute drive from Lake Michigan and 11 minutes from Four Winds Casino New Buffalo.

Hot Tub

Free WiFi

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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.