Chesterton Condo Rentals

A wooden staircase ascending a sandy hill with sparse vegetation.

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

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chesterton condo rentals

A wooden deck with a barbecue, outdoor seating, and a swing.

1. The RoofTop Skybar @ Lake Avenue Mansion #2

Michigan City

Jerry M.

HK$4,475 total

includes taxes & fees

8 Oct - 9 Oct

A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

2. Free Breakfast. Indoor Pool. Gym. Business Center.

Schererville

HK$2,205 total

includes taxes & fees

22 Oct - 23 Oct

3. 2 Bedroom | Free Daily Breakfast. Indoor Pool.

Schererville

HK$3,408 total

includes taxes & fees

22 Oct - 23 Oct

4. King Bed Suite | Indoor Pool. Free Breakfast.

Schererville

HK$3,408 total

includes taxes & fees

22 Oct - 23 Oct

View all properties

Find holiday rentals that suit your style

Cabins

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Chesterton Hotel Reviews

Blue Chip Casino Hotel and Spa

8/10 Good

"Love that they still have smoking rooms"

Furness Mansion

8/10 Good

"Nice place, cozy room. Near a noisy road and railroad - hard to ignore on the deck, but easy to ignore from our room. A part was missing from TV so it wouldn’t work. Help coming ‘soon’ meant 4 hours before a second TV was brought in. Polite but slow response and have seen no sign of the promised discount. But they did ask the maid to bring a box of microwave popcorn for us. Nice to be close to Indiana Dunes."

Waterbird Lakeside Inn

10/10 Excellent

"I arrived at the hotel after being discharged from a local hospital. I was traveling from NY to Colorado by motorcycle when I was hit by a truck. After 2 days in the hospital, I booked this hotel to recover, treat my wounds and wait for my motorcycle to be inspected. I ended up staying at Waterbird for 6 nights. The staff was amazing. So kind, caring and helpful. My room was quite large, comfortable and clean. The private lakeside deck was the perfect spot to drink morning coffee and relax while my wounds started to heal. Thank you so much, Missy and Max at the front desk. Thank you to Christina, Jessica, and Tracy, the housekeepers who made sure I had what I needed each day. I am truly grateful."

Find out more about Chesterton