Photo by Ruslian

Search Apartments in Chesterton

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • 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

Apartments in Chesterton

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

Porter
8.8 out of 10, Excellent, (16)
"Great place to stay with kids."
United States
Jane H.
The price is SAR 436
SAR 572 total
includes taxes & fees
17 Dec - 18 Dec
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

Chesterton
8.8 out of 10, Excellent, (90)
"Great location for visiting the Dunes. Having a gas grill available was a nice perk. Was what we needed at a great value. "
United States
Brian L.
The price is SAR 301
SAR 421 total
includes taxes & fees
8 Dec - 9 Dec
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

That 70’s Loft- Peace, Love and a Funky Stay!

2.0 star property
Chesterton
10.0 out of 10, Exceptional, (6)
"Absolutely lovely stay! Space was cozy and host was phenomenal!Amenities were on point, and the location was convenient for traveling to various points on the Dunes and trails! Would recommend anyone spend time at this rental, and would love to come back again!"
United States
Christopher B.
The price is SAR 659
SAR 1,230 total
includes taxes & fees
8 Dec - 9 Dec
That 70’s Loft- Peace, Love and a Funky Stay!

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Michigan City
9.4 out of 10, Exceptional, (126)
"Was as described great stay"
United States
Amber C.
The price is SAR 372
SAR 794 total
includes taxes & fees
8 Dec - 9 Dec
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Stay on State 2 bed

La Porte
8.8 out of 10, Excellent, (5)
"Beautiful apartment with the most responsive and kind host. "
United States
Kori M.
The price is SAR 354
SAR 532 total
includes taxes & fees
30 Dec - 31 Dec
Stay on State 2 bed

Heart of Historical Dist.*Parking*Claw Tub*A/C #4

Michigan City
10.0 out of 10, Exceptional, (7)
"This was the perfect place for a weekend getaway! Convenient location, clean apartment, and very responsive hosts. You can tell they put in a lot of effort and passion into their property. "
United States
Danielle S.
The price is SAR 341
SAR 863 total
includes taxes & fees
8 Dec - 9 Dec
Heart of Historical Dist.*Parking*Claw Tub*A/C #4

Heart of Historical Dist.*King*Parking*A/C*#1

Michigan City
10.0 out of 10, Exceptional, (2)
"Such a great stay. Close proximity to shopping and lake beach. The host is very professional and maintains a great property.Highly recommended the rental. "
United States
Aaron M.
The price is SAR 341
SAR 969 total
includes taxes & fees
8 Dec - 9 Dec
Heart of Historical Dist.*King*Parking*A/C*#1

UP*W/D*King*Balcony*10 min. to IN.Dunes & Beach

Michigan City
10.0 out of 10, Exceptional, (1)
"Wonderful accommodations. Love the beach so the beach chairs was a nice surprise. Walking distance to many shops and restaurants."
United States
Jay B.
The price is SAR 382
SAR 1,035 total
includes taxes & fees
8 Dec - 9 Dec
UP*W/D*King*Balcony*10 min. to IN.Dunes & Beach

The Beach Loft

Whiting
10.0 out of 10, Exceptional, (6)
"Very pleasant and has all the hotel commodities. Very clean, everything is within walking distance. The host is very friendly and willing to assist if needed. I highly recommend Beach Loft!! "
United States
Denise C.
The price is SAR 450
SAR 1,068 total
includes taxes & fees
8 Dec - 9 Dec
The Beach Loft

Luxe Michigan City Getaway-Private-Unit A

2.0 star property
Michigan City
The price is SAR 263
SAR 668 total
includes taxes & fees
7 Jan - 8 January 2026
Luxe Michigan City Getaway-Private-Unit A

The Moroccan Hideaway

Michigan City
10.0 out of 10, Exceptional, (3)
"Cute and cozy. "
United States
Irene D.
The price is SAR 571
SAR 1,379 total
includes taxes & fees
8 Dec - 9 Dec
The Moroccan Hideaway

Classic One-Bedroom apartment with King Bed

2.0 star property
La Porte
The price is SAR 348
SAR 1,028 total
includes taxes & fees
8 Dec - 9 Dec
Classic One-Bedroom apartment with King Bed

Private & Plush Retreat_Great Location!

Michigan City
The price is SAR 263
SAR 668 total
includes taxes & fees
14 Dec - 15 Dec
Private & Plush Retreat_Great Location!

Uptown Penthouse on Pine: By Lake Michigan, Shopping & Casino!

Michigan City
9.8 out of 10, Exceptional, (36)
"Great stay The place was great "
United States
Lisa M.
The price is SAR 470
SAR 1,228 total
includes taxes & fees
8 Dec - 9 Dec
Uptown Penthouse on Pine: By Lake Michigan, Shopping & Casino!

Boutique One Bedroom Apartment

La Porte
8.0 out of 10, Very Good, (1)
"Clean and spacious. Deck was great and the location was great for what I was looking for"
United States
J P.
The price is SAR 470
SAR 1,281 total
includes taxes & fees
8 Dec - 9 Dec
Boutique One Bedroom Apartment

Mainstay Mini

La Porte
The price is SAR 194
SAR 391 total
includes taxes & fees
29 Dec - 30 Dec
Mainstay Mini

Designer Loft Within Walking Distance to Restaurants, Bars & Beach! Pet Friendly

Michigan City
9.4 out of 10, Exceptional, (13)
"Excellent property with amazing restaurants! This place exceeded our expectations. I would definitely recommend to anyone visiting Michigan City. "
United States
Suzanne
The price is SAR 507
SAR 1,248 total
includes taxes & fees
8 Dec - 9 Dec
Designer Loft Within Walking Distance to Restaurants, Bars & Beach! Pet Friendly

Cozy loft inside a vintage store on an animal rescue farm in Westville, IN

Westville
10.0 out of 10, Exceptional, (9)
"Such a unique setup! Everything was nice and clean, the loft very comfortable and our hostess so gracious."
United States
Nur A.
The price is SAR 920
SAR 1,164 total
includes taxes & fees
8 Dec - 9 Dec
Cozy loft inside a vintage store on an animal rescue farm in Westville, IN

Sleeps 6*W/D*10 min. to IN.Dunes & Beach

Michigan City
The price is SAR 382
SAR 1,018 total
includes taxes & fees
8 Dec - 9 Dec
Sleeps 6*W/D*10 min. to IN.Dunes & Beach

Heart of Historical Dist.*W/D*Parking*Gl Shower #3

Michigan City
The price is SAR 341
SAR 850 total
includes taxes & fees
8 Dec - 9 Dec
Heart of Historical Dist.*W/D*Parking*Gl Shower #3
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesterton Hotel Reviews

Frequently asked questions

What's it like to stay at an apartment in Chesterton?
You'll find 9 apartments to choose from in Chesterton for your trip. While you're here, why not visit the shops and enjoy the beaches? Favorite sights to explore include Lake Michigan.
Why would you choose an apartment over a traditional hotel room?
Offering a kitchen for convenient meals, an apartment usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to stay in at night and plan out their next day, and also for families wanting the conveniences of home.
What's the best apartment for a stay in Chesterton?
Below is a top apartment in the area to consider: The Neighborhood Hotel - Grand Beach: Located in New Buffalo, 17.4 mi/28.1 km from Chesterton. Includes free WiFi, premium mattresses, and Smart TVs. Free parking and onsite laundry facilities are on site.
How many apartments should I expect to find in Chesterton?
Expedia has 9 apartments to book in Chesterton.
What can I expect from the weather in Chesterton?
Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Chesterton. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Chesterton are January, December, November, and February, with each month seeing an average of 6 inches of snowfall.
What should I see in Chesterton?
Chesterton is known for its beaches and shops. Lake Michigan and Indiana Dunes Visitor Center are a couple of scenic spots to enjoy the outdoors, whereas Chesterton Art Center is one of the cultural attractions. Lustron House and Chellberg Farm are other places to visit while you're in town.
What's the best way to get to and around Chesterton?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Chicago Midway Airport (MDW), which is located 37 mi (59.6 km) from the city center. Otherwise, look for flights into Chicago O'Hare Intl. Airport (ORD), which is 50.2 mi (80.7 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.