A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Family Hotels

Tonight
Sep 12 - Sep 13
Tomorrow
Sep 13 - Sep 14
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Chesterton family-friendly hotels

1. Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94
Chesterton
  • Experience family adventures near Indiana Dunes, where comfortable beds and nature trails create lasting memories.
NT$2,889
NT$3,235 total
includes taxes & fees
Oct 11 - Oct 12
Quality Inn Chesterton near Indiana Dunes National Park I-94

2. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
  • Discover a waterside haven for family adventure with an indoor pool and easy access to Indiana Dunes parks.
NT$4,631
NT$5,187 total
includes taxes & fees
Sep 20 - Sep 21
Hilton Garden Inn Chesterton

3. Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton
Chesterton
  • Family-friendly lodging near Indiana Dunes offers premium TV, free parking, and refrigerators for convenient adventures.
NT$2,563
NT$2,871 total
includes taxes & fees
Oct 1 - Oct 2
Fairbridge Inn Express Chesterton

4. Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
Chesterton
  • Family-friendly fun steps from Indiana Dunes National Park, with an indoor pool, hot tub, and complimentary breakfast for all.
NT$3,657
NT$4,096 total
includes taxes & fees
Oct 8 - Oct 9
Comfort Inn & Suites Porter near Indiana Dunes

5. Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park

Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
Chesterton
NT$9,370
NT$19,140 total
includes taxes & fees
Sep 27 - Sep 28
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park

6. Country Inn & Suites by Radisson, Portage, IN

Country Inn & Suites by Radisson, Portage, IN
Portage
  • Family-friendly hotel brings smiles to children's faces with an indoor pool, playground, and game room near Indiana Dunes National Park.
NT$4,169
NT$4,669 total
includes taxes & fees
Sep 27 - Sep 28
Country Inn & Suites by Radisson, Portage, IN
View all properties

Choose what matters most at family-friendly hotels in Chesterton

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Chesterton Hotel Reviews

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

8/10 Good
"What ud expect from a casino hot"
Charles 1-night trip
Posted 4 hours ago
Blue Chip Casino Hotel and Spa
Baymont by Wyndham New Buffalo

Baymont by Wyndham New Buffalo

8/10 Good
"As a whole, I truly enjoyed my stay at Baymont by Wyndam in New Buffalo, MI. The room that I stayed in was clean and comfortable (albeit missing a lightbulb in one of the lamps), I enjoyed my jacuzzi room, the indoor pool and gym (the air needs to be fixed in the gym, btw!) It was a very quiet and relaxing 3 days at the hotel, and I absolutely adore New Buffalo! However... I work in retail and have a management role at my job. I was absolutely appalled by the front desk employees lack of mere "friendliness" and making the guests "feel welcome" at this establishment. When I checked out this morning, the woman with the sour look on her face seemed bothered and burdened that I asked for my receipt! She didn't even ask, "how my stay was, etc."! I'm the one that said "have a nice day" first! The guy when I checked in wasn't much better! The housekeeping staff were a lot more pleasant to me when I asked for fresh towels, etc... Thank you! I gave the ranking I did, because I truly did enjoy my stay, however, perhaps some retraining is in order for the front desk clerks with their flippant and disconcerting attitude towards their guests! A smile and friendly attitude truly make the difference!"
Marleen 3-night trip
Posted 5 hours ago
Baymont by Wyndham New Buffalo
Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"Everything was perfect breakfast & cleanliness. Definitely would stay there again"
Marc 2-night trip
Posted 7 hours ago
Holiday Inn Express & Suites New Buffalo by IHG
Waterbird Lakeside Inn

Waterbird Lakeside Inn

10/10 Excellent
"The grandchildren loved fishing from hotel balcony. Was alot of fun"
LeAnne 1-night trip
Posted 10 hours ago
Waterbird Lakeside Inn
Comfort Inn Hammond I-94

Comfort Inn Hammond I-94

10/10 Excellent
"It was very clean food was g8"
Tolice 2-night trip
Posted 12 hours ago
Comfort Inn Hammond I-94
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

10/10 Excellent
"Ckean"
Jp 1-night trip
Posted 17 hours ago
Ameristar Casino Hotel East Chicago
Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton

8/10 Good
"Decent rooms with all the basic amenities. Biggest advantage is its proximity to all the major tourist destinations and convenience stores nearby."
Chandan 2-night trip
Posted 1 day ago
Fairbridge Inn Express Chesterton
Fairfield Inn and Suites By Marriott Merrillville

Fairfield Inn and Suites By Marriott Merrillville

8/10 Good
"The room was clean."
Georgene 1-night trip
Posted 3 days ago
Fairfield Inn and Suites By Marriott Merrillville
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

10/10 Excellent
"Perfect"
Jeannette 2-night trip
Posted 4 days ago
Hilton Garden Inn Chesterton

Frequently asked questions

What's Chesterton like for family-friendly vacations?
The relaxing destination of Chesterton is a great choice if you've been considering a vacation with the kids. The beaches, lake views, and coffee shops are just some of the things that make this an attractive family vacation spot. Take to the air and fly into Chicago Midway Airport (MDW), which is located 37 mi (59.6 km) from the city center.
What's the best place to stay for a family vacation in Chesterton?
Best Western Indian Oak is a hotel with an indoor pool and free parking, and it's a top choice on Expedia for families. Other good choices for your kid-friendly vacation include Comfort Inn & Suites Porter near Indiana Dunes and Quality Inn Chesterton near Indiana Dunes National Park I-94.
How many hotels that welcome families can I expect to find in Chesterton?
Expedia has 5 family-friendly hotels and other accommodations in Chesterton.
When's the best time to book a family-friendly vacation 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's there to see and do with your family in Chesterton?
While you are visiting Chesterton, you might want to round up the kiddos and make time to see interesting attractions such as Indiana Dunes Visitor Center and Indiana Dunes National Park. Make sure you have lots of time for activities like Chesterton Art Center and Chicago Street Theatre.

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