Search Guest Houses in Chesterton from CA $254

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
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Aug 29 - Aug 31
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Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Chesterton Guest Houses

Dream Retreat Guesthouse, Indiana Dunes Nat’l Park, 10 min hike to Beach
Beach nearby

Dream Retreat Guesthouse, Indiana Dunes Nat’l Park, 10 min hike to Beach

9.0 out of 10, Wonderful, (35)
"This is a nice property with a good location near the dunes. The path to the beach is beautiful, and the beach is perfect for families."
Dream Retreat Guesthouse, Indiana Dunes Nat’l Park, 10 min hike to Beach
Cozy Couples Retreat in Beachwalk Resort w/ Hot Tub
Outdoor pool, a heated pool

Cozy Couples Retreat in Beachwalk Resort w/ Hot Tub

9.8 out of 10, Exceptional, (47)
"On the smallish side but perfect for 2. Clean and cute!"
Cozy Couples Retreat in Beachwalk Resort w/ Hot Tub
Galien Suite
Fireplace

Galien Suite

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

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

10.0 out of 10, Exceptional, (52)
"We really enjoyed our stay at this property, and the fact that our hosts took the extra effort in ensuring we had access to a lot of everyday essentials. We definitely plan to return to this location when next we visit."
Chesterton “Golf View Estate” Midwest Great Lake Beaches & Trails Of The Dunes!
Luxury Guesthouse in private wooded setting in Grand Beach New Buffalo
Outdoor spa tub

Luxury Guesthouse in private wooded setting in Grand Beach New Buffalo

9.0 out of 10, Wonderful, (12)
"Owner was very attentive to any needs or questions we had during the stay. Would definitely book again! "
Luxury Guesthouse in private wooded setting in Grand Beach New Buffalo
Suite-Oversized-Ensuite with Jet bath-Courtyard view-SS Post Boy Suite
Fireplace

Suite-Oversized-Ensuite with Jet bath-Courtyard view-SS Post Boy Suite

Suite-Oversized-Ensuite with Jet bath-Courtyard view-SS Post Boy Suite
Snug Harbor
Fireplace

Snug Harbor

Snug Harbor
Beacons' Nest – Valpo U, Downtown & Dunes
Fridge, microwave, oven, stovetop

Beacons' Nest – Valpo U, Downtown & Dunes

Beacons' Nest – Valpo U, Downtown & Dunes
Miss Eber Knight
Fireplace

Miss Eber Knight

The price is CA $254
CA $312 total
includes taxes & fees
Sep 11 - Sep 12
Miss Eber Knight
Captain Whittaker - 2 bedroom, 2 bath
Fireplace

Captain Whittaker - 2 bedroom, 2 bath

The price is CA $378
CA $464 total
includes taxes & fees
Sep 11 - Sep 12
Captain Whittaker - 2 bedroom, 2 bath
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.
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Top Chesterton Hotel Reviews

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

10/10 Excellent
"Love coming to the dunes and staying at this nice hotel! My 3rd time in the last few years and I always have a good stay, very clean, friendly staff and convenient location!!"
Karen 1-night trip
Posted 16 hours ago
Hilton Garden Inn Chesterton