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Find Hotels with a Pool in Chesterton, IN

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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
$83 nightly
The price is $93
Jan 1 - Jan 2, 2026
Total with taxes and fees
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
$93 nightly
The price is $105
Dec 29 - Dec 30
Total with taxes and fees
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
$106 nightly
The price is $118
Dec 29 - Dec 30
Total with taxes and fees
Hilton Garden Inn Chesterton

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
9.0 out of 10, Wonderful, (12)
"Hosts are easy to communicate with and very nice. The pool barn is not part of the package. You will be able to swim and use the hot tub, however. We enjoyed the hot tub after a day of hiking! Cute town with interesting places to visit. "
United States
Sherri K.
$79 nightly
The price is $88
Dec 25 - Dec 26
Total with taxes and fees
The "Pool Barn Camper" w/Hot Tub 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
$90 nightly
The price is $101
Dec 28 - Dec 29
Total with taxes and fees
Comfort Inn & Suites Porter near Indiana Dunes

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
8.8 out of 10, Excellent, (16)
"Great place to stay with kids."
United States
Jane H.
$136 nightly
The price is $152
Dec 28 - Dec 29
Total with taxes and fees
The "Pool Barn" w/Pool, Hot Tub, Billiards & more 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
$84 nightly
The price is $94
Jan 9 - Jan 10, 2026
Total with taxes and fees
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, (1656)
"Great place, hotel room is very well appointed. "
United States
Stuart
$109 nightly
The price is $115
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
$81 nightly
The price is $91
Jan 2 - Jan 3, 2026
Total with taxes and fees
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
$68 nightly
The price is $72
Dec 29 - Dec 30
Total with taxes and fees
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 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.

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