Photo by Ruslian

Find Hotels with a Pool in Chesterton, IN

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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chesterton Hotels with a Pool

Our top choices for Chesterton hotels with a pool

Indoor pool
Spring House Inn

Spring House Inn

Spring House Inn
2.5 star property
Chesterton
9.0 out of 10, Wonderful, (1002)
"Beautiful Hotel"
United States
Joseph
The price is ₩116,015
₩137,280 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Spring House Inn
Indoor pool
Best Western Indian Oak

Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1003)
"It was very nice, with great access to the national park."
United States
leona ann
The price is ₩137,295
₩153,769 total
includes taxes & fees
Dec 23 - Dec 24
Best Western Indian Oak
Indoor pool
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1003)
"We loved staying here. "
United States
Linda
The price is ₩155,343
₩173,984 total
includes taxes & fees
Dec 24 - Dec 25
Hilton Garden Inn Chesterton
Indoor spa tub
Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
2.5 star property
Chesterton
8.0 out of 10, Very Good, (1002)
"Nice and close to the beach."
United States
Alison
The price is ₩133,300
₩149,296 total
includes taxes & fees
Dec 21 - Dec 22
Comfort Inn & Suites Porter near Indiana Dunes
Seasonal outdoor pool, pool umbrellas, sun loungers
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo
3.5 star property
New Buffalo
9.4 out of 10, Exceptional, (1644)
"Great place, hotel room is very well appointed. "
United States
Stuart
The price is ₩130,848
₩151,790 total
includes taxes & fees
Dec 17 - Dec 18
Four Winds Casino Resort – New Buffalo
Indoor pool
Hampton Inn & Suites Valparaiso

Hampton Inn & Suites Valparaiso

Hampton Inn & Suites Valparaiso
2.5 star property
Valparaiso
8.8 out of 10, Excellent, (808)
"Everything was great!"
United States
Matt
The price is ₩151,554
₩169,741 total
includes taxes & fees
Dec 28 - Dec 29
Hampton Inn & Suites Valparaiso
Exterior
Hampton Inn & Suites Michigan City

Hampton Inn & Suites Michigan City

Hampton Inn & Suites Michigan City
2.5 star property
Michigan City
8.6 out of 10, Excellent, (914)
"Comfortable, clean, well furnished; excellent breakfast 👍👍👍"
United States
Eduardo
The price is ₩140,678
₩157,559 total
includes taxes & fees
Dec 26 - Dec 27
Hampton Inn & Suites Michigan City
Indoor pool, open 10:00 AM to 11:00 PM, sun loungers
Holiday Inn Express & Suites La Porte by IHG

Holiday Inn Express & Suites La Porte by IHG

Holiday Inn Express & Suites La Porte by IHG
2.5 star property
La Porte
9.0 out of 10, Wonderful, (628)
"Very good point to stay"
United States
Peter
The price is ₩136,575
₩152,963 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express & Suites La Porte by IHG
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

Top Chesterton Hotel Reviews

Baymont by Wyndham New Buffalo

Baymont by Wyndham New Buffalo

10/10 Excellent
"Staff was friendly. Room was clean. Breakfast was nothing to brag about. Also the pool and hot tub are both out of order at the time which was disappointing bc it was one of the reasons we booked this hotel. They do have a jacuzzi room, which was what we booked thankfully and that was nice and worked properly. "
Jared 2-night trip
Posted 6 days ago
Baymont by Wyndham New Buffalo

Frequently asked questions

What are some accommodations with pools in Chesterton?
Comfort Inn & Suites Porter near Indiana Dunes: Hotel located near Indiana Dunes National Park. Features daily, an indoor pool, and free self parking. Spring House Inn: Hotel, 10-minute walk from Indiana Dunes National Park. Offers a sauna, an indoor pool, and daily. Hilton Garden Inn Chesterton: Provides a snack bar/deli, an indoor pool, and free self parking. Best Western Indian Oak: Hotel located near Indiana Dunes National Park. Features a sauna, an indoor pool, and free self parking. Waterbird Lakeside Inn: Hotel steps from Four Winds Casino New Buffalo. Features 4 restaurants, a seasonal outdoor pool, and 3 bars.
What is there to see and do in Chesterton?
Explore places like Lake Michigan while you're in Chesterton. Surround yourself with nature at Indiana Dunes Visitor Center and Indiana Dunes National Park. The beaches, lakeside setting, and restaurants are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Chesterton?
You may want to consider a place to stay with an outdoor swimming pool if you're planning to visit Chesterton in the hottest months of July, August, or June when the average temperature is 70°F. Lodging with an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temp is 31°F.