Hotels With Pool in Chesterton, IN - Top 10 Chesterton Indiana Hotels

Q: What are some accommodations with pools in Chesterton?

Spring House Inn : Hotel, 10-minute walk from Indiana Dunes National Park. Features a sauna, an indoor pool, and daily. Best Western Indian Oak : Hotel located near Indiana Dunes National Park. Offers a sauna, an indoor pool, and free self parking. Waterbird Lakeside Inn : Offers a snack bar/deli, an indoor pool, and free self parking. Quality Inn Chesterton near Indiana Dunes National Park I-94 : Hotel located near Indiana Dunes National Park. Features daily, an indoor pool, and free self parking. Hilton Garden Inn Chesterton : Offers complimentary wireless internet access, a pool, and kitchens.

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Our top choices for Chesterton hotels with a pool

Seasonal outdoor pool, pool umbrellas, sun loungers

Four Winds Casino Resort – New Buffalo

New Buffalo

Dive into the seasonal outdoor pool surrounded by loungers, where live music creates a relaxing getaway atmosphere.

$109 nightly

May 20 - May 21

Total with taxes and fees

Spring House Inn

Chesterton

Relax in the heated indoor pool surrounded by forest views at this tranquil retreat.

$123 nightly

May 20 - May 21

Total with taxes and fees

The Blue Heron Inn

La Porte

Lakeside pool oasis comes alive with sunsets, boat rentals, and creature comforts by Pine Lake.

$109 nightly

May 21 - May 22

Total with taxes and fees

Holiday Inn Express Valparaiso by IHG

Valparaiso

Dive into a crystal-clear indoor pool sanctuary at this Valparaiso retreat where comfort meets convenience in every splash.

$109 nightly

May 24 - May 25

Total with taxes and fees

Best Western Indian Oak

Chesterton

Discover serene lakeside swimming in a peaceful Indiana Dunes retreat, where the indoor pool welcomes year-round relaxation.

$93 nightly

May 25 - May 26

Total with taxes and fees

Hilton Garden Inn Chesterton

Chesterton

Dive into the sparkling indoor pool oasis, just steps from Indiana Dunes National Park.

$134 nightly

May 31 - Jun 1

Total with taxes and fees

Comfort Inn & Suites Porter near Indiana Dunes

Chesterton

Splash into relaxation with an indoor pool and rejuvenating hot tub at this Indiana Dunes retreat.

$108 nightly

May 24 - May 25

Total with taxes and fees

Hampton Inn & Suites Michigan City

Michigan City

Dive into refreshing relaxation at this Michigan City hotel with a spotless indoor pool and daily complimentary breakfast buffet.

$106 nightly

May 31 - Jun 1

Total with taxes and fees

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Choose what matters most at hotels with a pool in Chesterton

Breakfast included

Hot tub

Top Chesterton Hotel Reviews

Best Western Indian Oak

10/10 Excellent

"The breakfast was ample, with plenty of hot and cold options. The pool was fine, and the sauna was an added benefit. I wasn't expecting to do birdwatching from the motel, but it is on a small lake, and there were egrets and lots of other birds very nearby. The shower was easily accessible (my husband uses a wheelchair)."

Country Inn & Suites by Radisson, Merrillville, IN

4/10 Poor

"The coffee in the lobby was cold, even during peak breakfast hours. We were told to park on the end of the building closest to our room, but the door was broken and couldn’t be used. Our keys didn't work when we first checked in. The body wash and shampoo were completely empty in the shower. The person that brought us the bottles didn't know how to install the new one. The vending machine charged me $5 for a drink I didn't get. There were no towels in the pool area. We weren't allowed to have fresh towels in our room without giving the dirty ones to the front desk. And I was charged a full three hours of early check in when it was maximum 2 hours, which seems unfair when the hotel isn't sold out and the room clearly hasn't been used or cleaned in a while."

Blue Chip Casino Hotel and Spa

10/10 Excellent

"The room was clean and well maintained, the property was definitely well taken care of. The pool, however, was closed due to maintenance and the coffee machine never worked in the only breakfast place to get a coffee. I missed that it's a smoking casino, something I typically wouldn't spend time at, but overall it was a good experience. They were a bit short staffed and couldn't open certain gaming tables bc of it and the area around the resort didn't have much else going on but we had a good time regardless."

Frequently asked questions

What are some accommodations with pools in Chesterton?

Spring House Inn: Hotel, 10-minute walk from Indiana Dunes National Park. Features a sauna, an indoor pool, and daily. Best Western Indian Oak: Hotel located near Indiana Dunes National Park. Offers a sauna, an indoor pool, and free self parking. Waterbird Lakeside Inn: Offers a snack bar/deli, an indoor pool, and free self parking. Quality Inn Chesterton near Indiana Dunes National Park I-94: Hotel located near Indiana Dunes National Park. Features daily, an indoor pool, and free self parking. Hilton Garden Inn Chesterton: Offers complimentary wireless internet access, a pool, and kitchens.

What is there to see and do in Chesterton?

Explore places like Indiana Dunes National Park and Lake Michigan while you're in Chesterton. Surround yourself with nature at Indiana Dunes Visitor Center and Coffee Creek Watershed Conservancy Preserve. 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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