Book Guest Houses in Chesterton, IN
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Top Guest Houses in Chesterton
Luxury Guesthouse in private wooded setting in Grand Beach New Buffalo
New Buffalo MI
$400 nightly
The price is $400 total per night
$400 total
Dec 9 - Dec 10
Total with taxes and fees
This guesthouse includes a garden and laundry facilities.
Pet friendly
Air conditioning
Elyon Hall CoachHouse, Indiana Dunes Nat’l Park, 10 min hike to Beach
Miller Beach IN
This guesthouse features free WiFi in public areas, laundry facilities, and self parking. Barbecue grills are provided for your convenience.
Pet friendly
Free WiFi
Cozy Couples Retreat in Beachwalk Resort w/ Hot Tub
Michigan City IN
An outdoor pool is featured at this guesthouse, along with laundry facilities and concierge services. Barbecue grills are provided for your convenience.
Pool
Air conditioning
Captain Whittaker Suite 2 bedroom, 2 baths
New Buffalo MI
A hot tub is featured at this guesthouse, along with laundry facilities.
Hot Tub
Free WiFi
Galien Room Suite King size with Jacuzzi
New Buffalo MI
A hot tub is available at this guesthouse.
Hot Tub
Free WiFi
Beacons' Nest – Valpo U, Downtown & Dunes
Valparaiso IN
Free Cancellation
$218 nightly
The price is $244 total per night
$244 total
Dec 11 - Dec 12
Total with taxes and fees
This guesthouse features a water park, a garden, and laundry facilities.
Pet friendly
Free WiFi
Chesterton “Golf View Estate” Midwest Great Lake Beaches & Trails Of The Dunes!
Chesterton IN
This guesthouse features a garden, laundry facilities, and barbecue grills.
Free WiFi
Air conditioning
SS Post Boy Queen Suite with Jacuzzi
New Buffalo MI
A hot tub is featured at this guesthouse, along with a garden.
Hot Tub
Free WiFi
Eber Knight Studio - King size with Jacuzzi
New Buffalo MI
$199 nightly
The price is $213 total per night
$213 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
A hot tub is available at this guesthouse.
Hot Tub
Free WiFi
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.
Top hotels in Chesterton
Spring House Inn
303 N Mineral Springs Rd Chesterton IN
$93 nightly
The price is $105 total per night from Dec 9 to Dec 10
$105 total
Dec 9 - Dec 10
Total with taxes and fees
8.8/10 Excellent! (1,019 reviews)
Chesterton Guest Houses essential information
Accommodation | 10 Guest Houses |
|---|---|
Lowest Price | $85 |
Highest Price | $400 |
Popular accommodation | Luxury Guesthouse in private wooded setting in Grand Beach New Buffalo, Elyon Hall CoachHouse, Indiana Dunes Nat’l Park, 10 min hike to Beach, Cozy Couples Retreat in Beachwalk Resort w/ Hot Tub, Captain Whittaker Suite 2 bedroom, 2 baths, Galien Room Suite King size with Jacuzzi, Beacons' Nest – Valpo U, Downtown & Dunes, Chesterton “Golf View Estate” Midwest Great Lake Beaches & Trails Of The Dunes!, SS Post Boy Queen Suite with Jacuzzi, Eber Knight Studio - King size with Jacuzzi, Snug Harbor Suite - King with Jacuzzi |
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