Search Guest Houses in Chesterton from CA $287

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Chesterton Guest Houses

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! "
The price is CA $287
CA $571 total
includes taxes & fees
Dec 26 - Dec 27
Luxury Guesthouse in private wooded setting in Grand Beach New Buffalo
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)
"This was our 2nd time staying at this property & it’s perfect in every way."
Chesterton “Golf View Estate” Midwest Great Lake Beaches & Trails Of The Dunes!
Couples Getaway! Studio w/ Queen
Outdoor pool, a heated pool

Couples Getaway! Studio w/ Queen

9.8 out of 10, Exceptional, (47)
"On the smallish side but perfect for 2. Clean and cute!"
Couples Getaway! Studio w/ Queen
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.
Don't see what you're looking for?
See all available properties in Chesterton
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chesterton

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Interior

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

10.0 out of 10, Exceptional, (74)
"My husband, 2 year old daughter, and I needed to find a place last minute to stay in Northern Indiana and stumbled upon this. We had no idea that there was a National/State Sand Dune park, or a beautiful beach in this area. We were beyond excited to find this beautiful gem of a cottage to stay in. "
The price is CA $258
CA $421 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Blue Birdhouse by the Beach
Property grounds

Blue Birdhouse by the Beach

9.2 out of 10, Wonderful, (21)
"We had a fantastic stay at the Blue Birdhouse. Super close to the beach and a very clean little house. Wagners Ribs were walking distance away and delicious food. We had an issue accessing the house that the owner quickly resolved. Great little place. "
The price is CA $171
CA $355 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Blue Birdhouse by the Beach
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Beach nearby

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

9.8 out of 10, Exceptional, (8)
"Would reserve this again wonderful host"
The price is CA $113
CA $159 total
includes taxes & fees
Dec 30 - Dec 31
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
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.