Photo by Susan Ross

Search Apartments in Chesterton

  • 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

Find vacation rentals that suit your style

Apartment image
Apartments
Apartments
cabin image
Cabins
Cabins

Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Chesterton apartments

A beach with a parking lot and buildings in the background.

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

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Chesterton
8.8 out of 10, Excellent, (141 reviews)
"Perfect for location to walk to local winery or brewery for a little fancy and fancy-free!We’d recommend"
United States
Laura H.
The price is AED 437
AED 510 total
includes taxes & fees
9 Nov - 10 Nov
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
A beach with sand dunes and grass.

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

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Porter
9.0 out of 10, Wonderful, (22 reviews)
"Awesome place to stay and plenty to do"
United States
Cody
The price is AED 731
AED 884 total
includes taxes & fees
29 Nov - 30 Nov
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

3. 2 Full Bed | Non-Smoking

2 Full Bed | Non-Smoking
Portage
9.6 out of 10, Exceptional, (67 reviews)
"This was one of the worst places I have stayed in! The place was in sad need of repairs and although it said no smoking the lobby smelled strongly of smoke, The whole place seemed unclean. I would not recommend it nor will i ever stay there again."
United States
Jacki
The price is AED 337
AED 419 total
includes taxes & fees
8 Nov - 9 Nov
2 Full Bed | Non-Smoking
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

4. Premium King Bed|Portage

Premium King Bed|Portage
Portage
10.0 out of 10, Exceptional, (65 reviews)
"Sketchy property location, not clearly marked on the street (kind of hard to find), unnecessary poor communication regarding check-in procedures, (just like a regular front desk experience but they make it complicated) The room was ok, bed was fine, staff was very helpful, property condition was just ok."
United States
Dave
The price is AED 362
AED 452 total
includes taxes & fees
8 Nov - 9 Nov
Premium King Bed|Portage
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

5. King Bed | Non-Smoking

King Bed | Non-Smoking
Portage
10.0 out of 10, Exceptional, (68 reviews)
"The place is not clean and it smells really bad. It did not look anything like the pictures."
United States
Luis
The price is AED 337
AED 419 total
includes taxes & fees
8 Nov - 9 Nov
King Bed | Non-Smoking
A hotel lobby with a dining area, seating, a reception desk, and a fire extinguisher.

6. Full Bed Accessible|Portage

Full Bed Accessible|Portage
Portage
10.0 out of 10, Exceptional, (82 reviews)
"Spotless bathrooms with enough towels were greatly appreciated, cleanliness makes such a difference!"
United States
Anonymous traveler
The price is AED 313
AED 391 total
includes taxes & fees
8 Nov - 9 Nov
Full Bed Accessible|Portage
A hotel lobby with a dining area, a reception desk, and a computer station.

7. King Bed | Non-Smoking

King Bed | Non-Smoking
Portage
10.0 out of 10, Exceptional, (83 reviews)
"Loved how peaceful it was. Perfect place to recharge after our daily outings."
United States
Anonymous traveler
The price is AED 401
AED 500 total
includes taxes & fees
8 Nov - 9 Nov
King Bed | Non-Smoking
A hotel lobby with a dining area, a reception desk, and a seating area with chairs and a table.

8. Premium King Room with Jetted Tub

Premium King Room with Jetted Tub
Portage
10.0 out of 10, Exceptional, (84 reviews)
"Hot shower was refreshing after a long day out exploring. Nice little touches made it feel cozy."
United States
Anonymous traveler
The price is AED 739
AED 919 total
includes taxes & fees
8 Nov - 9 Nov
Premium King Room with Jetted Tub
A hotel room with two beds, a desk, a TV, and a seating area with a sofa and chairs.

9. Portage|Suite - Two Double

Portage|Suite - Two Double
Portage
10.0 out of 10, Exceptional, (48 reviews)
"Spacious area for two people, felt cozy yet roomy enough for comfort while hanging out together."
United States
Anonymous traveler
The price is AED 401
AED 500 total
includes taxes & fees
13 Nov - 14 Nov
Portage|Suite - Two Double
A lighthouse by the sea with a pier extending into the water.

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

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Michigan City
9.2 out of 10, Wonderful, (144 reviews)
"Its was ok"
United States
Amber C.
The price is AED 459
AED 967 total
includes taxes & fees
8 Nov - 9 Nov
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
A living room with a sofa, armchair, coffee table, and a lamp.

11. Downtown Getaway 2

Downtown Getaway 2
Michigan City
9.2 out of 10, Wonderful, (40 reviews)
"Clean property, easy parking, nice area"
United States
Sandi B.
The price is AED 380
AED 755 total
includes taxes & fees
9 Nov - 10 Nov
Downtown Getaway 2
A staircase leading to a second floor in a building with a rustic interior, wooden beams, and a vintage poster on the wall.

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

Cozy loft inside a vintage store on an animal rescue farm in Westville, IN
Westville
10.0 out of 10, Exceptional, (18 reviews)
"The property was beautiful, spotlessly clean, and Jen was the perfect hostess. This was one of our favorite places we've ever stayed."
United States
Jessica H.
The price is AED 900
AED 1,094 total
includes taxes & fees
8 Nov - 9 Nov
Cozy loft inside a vintage store on an animal rescue farm in Westville, IN
A large, multi-story building with arched windows and a flat roof, situated on a sandy area with a reflective water surface in the foreground.

13. Private & Plush Retreat_Great Location!

Private & Plush Retreat_Great Location!
Michigan City
The price is AED 261
AED 733 total
includes taxes & fees
9 Nov - 10 Nov
Private & Plush Retreat_Great Location!
A two-story brick building with a black front door, white trim, and a number '621' above the door. There are two potted plants on either side of the door, and a small garden area with trimmed bushes.

14. The Moroccan Hideaway

The Moroccan Hideaway
Michigan City
9.8 out of 10, Exceptional, (7 reviews)
"Renee is a great host. She met us and made sure we were comfortable. We are looking for a halfway place for family weekends and will definitely book again. Very close to Franklin street with fun shops and good restaurants."
United States
Bea S.
The price is AED 459
AED 1,165 total
includes taxes & fees
8 Nov - 9 Nov
The Moroccan Hideaway
A modern living room with a sofa, armchair, and a coffee table. There is a bunk bed in the background, a large rug, and a ceiling fan.

15. Dunes & Beach Getaway - Sleeps 10 - Room for the Whole Crew

Dunes & Beach Getaway - Sleeps 10 - Room for the Whole Crew
Portage
The price is AED 1,980
AED 3,629 total
includes taxes & fees
8 Nov - 9 Nov
Dunes & Beach Getaway - Sleeps 10 - Room for the Whole Crew
A two-story brick house with a front porch, a black door, and a number '621' above the door.

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

Uptown Penthouse on Pine: By Lake Michigan, Shopping & Casino!
Michigan City
9.8 out of 10, Exceptional, (54 reviews)
"Great place, would stay again."
United States
Zakhar S.
The price is AED 526
AED 1,222 total
includes taxes & fees
8 Nov - 9 Nov
Uptown Penthouse on Pine: By Lake Michigan, Shopping & Casino!
A reception desk with a staff member, a guest, and a child.

17. 1 King Bed | Micfridge

1 King Bed | Micfridge
MERRILLVILLE
10.0 out of 10, Exceptional, (4 reviews)
"Loved how quick check-in was!"
United States
Anonymous traveler
The price is AED 291
AED 325 total
includes taxes & fees
9 Nov - 10 Nov
1 King Bed | Micfridge
Beach

18. The Greengrass Getaway

The Greengrass Getaway
Michigan City
7.6 out of 10, Good, (4 reviews)
"We liked the location. It would've been nice to have more towels, washcloths, laundry soap, and more than 1 roll of toilet paper, instructions for the TV. Information on the area and tourist attractions. We will definitely recommend this place. We enjoyed exploring places."
United States
Kaylene G.
The price is AED 621
AED 1,201 total
includes taxes & fees
2 Dec - 3 Dec
The Greengrass Getaway
A bedroom with a large bed, a ceiling fan, a desk, and a TV.

19. Classic One-Bedroom apartment with King Bed

Classic One-Bedroom apartment with King Bed
La Porte
9.0 out of 10, Wonderful, (2 reviews)
"Very accommodating given our situation. Easy to get ahold of and fast at trouble shooting. It's a really nice place in a good part of town. We appreciated them so much"
United States
Stephanie D.
The price is AED 371
AED 980 total
includes taxes & fees
8 Nov - 9 Nov
Classic One-Bedroom apartment with King Bed
A two-story brick building with a black facade, large windows, and a prominent entrance.

20. Boutique Studio Apartment

Boutique Studio Apartment
La Porte
8.0 out of 10, Very good, (1 review)
"My bf, dogs, and I had planned a spur of the moment trip. The host was very attentive to our needs. The studio apartment was very clean with modern updates throughout."
United States
Nicole S.
The price is AED 410
AED 1,127 total
includes taxes & fees
8 Nov - 9 Nov
Boutique Studio Apartment
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.
View all properties

Learn more about Chesterton

Nestled along Lake Michigan's shore, this small town offers scenic trails through Indiana Dunes National Park for hiking and birdwatching. Coffee shops and local restaurants line the historic downtown, while nearby beaches provide perfect spots for summer swimming and sunset views.

See all hotels in Chesterton
A wooden staircase leading up a sandy hill with dense green forest in the background.
Photo by Susan Ross
Open Photo by Susan Ross

Top reviews in Chesterton

A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton

10/10 Excellent

Nice decor, clean room.
United States
anne
Reviewed December 26, 2022
Hilton Garden Inn Chesterton

Frequently Asked Questions

What's it like to stay at an apartment in Chesterton?

You'll find 8 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?

Here's a favorite apartment in the area to consider: The Neighborhood Hotel - Grand Beach: Located 17.4 mi/28.1 km away in New Buffalo. Free WiFi, premium mattresses, and Smart TVs are included. Free parking and onsite laundry facilities are on site.

How many apartments should I expect to find in Chesterton?

Expedia has 8 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 Bailly Homestead - American Indians and Fur Traders 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.