A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Family Hotels

Tonight
17 Aug - 18 Aug
Tomorrow
18 Aug - 19 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Chesterton family-friendly hotels

Lobby
Lobby
Standard Room, 2 Queen Beds, Non Smoking | Down comforters, desk, laptop workspace, blackout drapes
Standard Room, 1 King Bed, Non Smoking | Down comforters, desk, laptop workspace, blackout drapes

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.
AED 334
AED 374 total
includes taxes & fees
15 Sep - 16 Sep
Quality Inn Chesterton near Indiana Dunes National Park I-94
Lobby
Fitness facility
Lobby
One king bed junior suite | Desk, laptop workspace, blackout drapes, soundproofing

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.
AED 560
AED 627 total
includes taxes & fees
31 Aug - 1 Sep
Hilton Garden Inn Chesterton
Restaurant
Standard Room, 2 Double Beds | 1 bedroom, premium bedding, desk, iron/ironing board
Reception
Reception

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.
AED 331
AED 370 total
includes taxes & fees
6 Sep - 7 Sep
Fairbridge Inn Express Chesterton
Children's area
Property grounds
Outdoor pool, a heated pool
Beach nearby

4. 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
AED 826
AED 1,053 total
includes taxes & fees
23 Aug - 24 Aug
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Smart TV, fireplace, books
Combined shower/tub, hair dryer, towels
3 bedrooms, desk, iron/ironing board, WiFi (free)
Coffee/tea maker, fridge, microwave, oven

5. Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes

Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
Chesterton
AED 420
AED 1,429 total
includes taxes & fees
3 Sep - 4 Sep
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
Exterior
Smart TV, books
Coffee/tea maker, fridge, microwave, oven
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

6. The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Porter
AED 459
AED 1,004 total
includes taxes & fees
8 Sep - 9 Sep
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Lobby
Free daily continental breakfast
Desk, iron/ironing board, cribs (surcharge), rollaway beds (surcharge)
Indoor pool

7. 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.
AED 418
AED 469 total
includes taxes & fees
8 Sep - 9 Sep
Comfort Inn & Suites Porter near Indiana Dunes
Beach
Coffee/tea maker, fridge, microwave, oven
Terrace/patio
Shower, hair dryer, towels, soap

8. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
Tower Haus w/Private Hot Tub
WiFi (free)
Gift shop
Reception

9. Home2 Suites by Hilton Michigan City

Home2 Suites by Hilton Michigan City
Michigan City
AED 509
AED 570 total
includes taxes & fees
30 Aug - 31 Aug
Home2 Suites by Hilton Michigan City
Indoor pool
Lobby
Exterior
Room, 1 King Bed, Non Smoking | Tempur-Pedic beds, desk, blackout drapes, iron/ironing board

10. 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.
AED 543
AED 608 total
includes taxes & fees
27 Aug - 28 Aug
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

Quality Inn Near Interstate I94

Quality Inn Near Interstate I94

10/10 Excellent
"My best friend and I love staying at The Quality Inn in New Buffalo. It’s always clean. The staff is friendly and welcoming. We always stay there for a girls trip! Their continental breakfast is delicious. I would definitely recommend staying at this hotel. You can’t beat the price. We usually go during the week and we have the pool all to ourselves."
Melissa 1-night trip
Posted less than an hour ago
Quality Inn Near Interstate I94
Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Clean room"
Patrick 1-night trip
Posted 18 hours ago
Best Western Indian Oak
Baymont by Wyndham New Buffalo

Baymont by Wyndham New Buffalo

8/10 Good
"Clean, comfortable room!"
Mara 3-night trip
Posted 2 days ago
Baymont by Wyndham New Buffalo
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

10/10 Excellent
"the staff was super nice!"
Makayla 1-night trip
Posted 2 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 Hilton Garden Inn Chesterton.
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 National Park and Indiana Dunes Visitor Center. Make sure you have plenty of time to take in the area's activities like Indiana Dunes State Park and Lake Michigan.