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Hotels with Swimming Pools in Chesterton

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Our top choices for Chesterton hotels with a pool

Spring House Inn

Spring House Inn
2.5 star property
Chesterton
8.8 out of 10, Excellent, (1002)
"Beautiful Hotel"
United States
Joseph
The price is S$120
includes taxes & fees
1 Jan - 2 Jan, 2026
Spring House Inn

Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1001)
"The room's clean and comfy, the staff super helpful, thank you!"
United States
Dmytro
The price is S$134
includes taxes & fees
5 Jan - 6 Jan, 2026
Best Western Indian Oak

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1003)
"Amazing! Very clean, comfortable and great service for the reasonable price. Hotel bar food and drinks were good and the staff was very friendly!"
Canada
Ryan
The price is S$159
includes taxes & fees
11 Jan - 12 Jan, 2026
Hilton Garden Inn Chesterton

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, (1003)
"Nice and close to the beach."
United States
Alison
The price is S$136
includes taxes & fees
25 Jan - 26 Jan, 2026
Comfort Inn & Suites Porter near Indiana Dunes

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo
3.5 star property
New Buffalo
9.4 out of 10, Exceptional, (1670)
"Great place, hotel room is very well appointed. "
United States
Stuart
The price is S$133
includes taxes & fees
4 Jan - 5 Jan, 2026
Four Winds Casino Resort – New Buffalo

Holiday Inn Express Valparaiso by IHG

Holiday Inn Express Valparaiso by IHG
2.5 star property
Valparaiso
8.4 out of 10, Very good, (775)
"Room clean, nice fitness & pool areas, whole hotel felt new (apparently recently remodeled). Breakfast was pretty good with lots of choices, and the coffee was really good! and the "breakfast lady", Martina, was super helpful & friendly "
United States
Melanie
The price is S$134
includes taxes & fees
9 Jan - 10 Jan, 2026
Holiday Inn Express Valparaiso by IHG

Hampton Inn Crown Point

Hampton Inn Crown Point
2.5 star property
Crown Point
9.4 out of 10, Exceptional, (622)
"Hotel is only about a year old and very nice. Staff was friendly at check-in and breakfast. Would stay here again if in the area."
United States
Tara
The price is S$152
includes taxes & fees
8 Jan - 9 Jan, 2026
Hampton Inn Crown Point

Quality Inn Near Interstate I94

Quality Inn Near Interstate I94
2.5 star property
New Buffalo
8.4 out of 10, Very good, (1067)
"Friendly staff - clean room!"
United States
Maureen
The price is S$92
includes taxes & fees
5 Jan - 6 Jan, 2026
Quality Inn Near Interstate I94
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.

Top Chesterton Hotel Reviews

Frequently asked questions

What are some accommodation options with pools in Chesterton?
Comfort Inn & Suites Porter near Indiana Dunes: Features daily, an indoor pool and free self parking. Hilton Garden Inn Chesterton: Offers a snack bar/deli, an indoor pool and free self parking. Best Western Indian Oak: Hotel located near Indiana Dunes National Park. Provides a sauna, an indoor pool and free self parking. Spring House Inn: Hotel, 10-minute walk from Indiana Dunes National Park. Features a sauna, an indoor pool and daily. Waterbird Lakeside Inn: Hotel steps from Four Winds Casino New Buffalo. Offers 4 restaurants, a seasonal outdoor pool and 3 bars.
What is there to see and do in Chesterton?
Explore places such as 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 that has an outdoor pool if you're planning to visit Chesterton in the hottest months of July, August or June, when the average temperature is 21°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is 0°C.

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