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Search Hotels with Pool 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 2.078.885 ₫
2.459.926 ₫ total
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, (1003)
"The room's clean and comfy, the staff super helpful, thank you!"
United States
Dmytro
The price is 2.460.189 ₫
2.755.413 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Best Western Indian Oak

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1001)
"We loved staying here. "
United States
Linda
The price is 2.783.601 ₫
3.117.633 ₫ total
includes taxes & fees
28 Dec - 29 Dec
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, (1002)
"Nice and close to the beach."
United States
Alison
The price is 2.363.613 ₫
2.647.247 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites Porter near Indiana Dunes

Holiday Inn Express & Suites Merrillville by IHG

Holiday Inn Express & Suites Merrillville by IHG
2.5 star property
Merrillville
8.4 out of 10, Very good, (758)
"Stay was great. Staff very welcoming, room was clean, beds were soft and refreshing and not noisy. Breakfast has a good spread good selection. Front desk was very helpful and nice. Would definitely stay here again."
Canada
christina
The price is 2.210.460 ₫
2.475.715 ₫ total
includes taxes & fees
9 Jan - 10 Jan 2026
Holiday Inn Express & Suites Merrillville by IHG

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo
3.5 star property
New Buffalo
9.4 out of 10, Exceptional, (1651)
"Great place, hotel room is very well appointed. "
United States
Stuart
The price is 2.344.667 ₫
2.719.919 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Four Winds Casino Resort – New Buffalo

Hampton Inn Portage

Hampton Inn Portage
2.5 star property
Portage
7.8 out of 10, Good, (811)
"The staff was courteous and the amenities guest friendly. I would consider another stay, on my next trip to Portage."
United States
Janice
The price is 2.136.252 ₫
2.392.602 ₫ total
includes taxes & fees
9 Jan - 10 Jan 2026
Hampton Inn Portage

Quality Inn Near Interstate I94

Quality Inn Near Interstate I94
2.5 star property
New Buffalo
8.4 out of 10, Very good, (1059)
"Friendly staff - clean room!"
United States
Maureen
The price is 1.776.263 ₫
1.882.839 ₫ total
includes taxes & fees
28 Dec - 29 Dec
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 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.