The Best Hotels with a Pool in Chesterton, IN from ￥14,283 in 2026

Q: What are some accommodations with pools in Chesterton?

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

A wooden staircase ascending a sandy hill with sparse vegetation.

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Our top choices for Chesterton hotels with a pool

1. Best Western Indian Oak

Chesterton

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

￥23,238 total

includes taxes & fees

Aug 17 - Aug 18

2. Spring House Inn

Chesterton

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

￥24,058 total

includes taxes & fees

Aug 30 - Aug 31

3. Hilton Garden Inn Chesterton

Chesterton

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

￥26,385 total

includes taxes & fees

Aug 20 - Aug 21

4. Comfort Inn & Suites Porter near Indiana Dunes

Chesterton

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

￥21,076 total

includes taxes & fees

Aug 31 - Sep 1

5. The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

Porter

Unwind at dual-pool retreat near Indiana Dunes National Park featuring hot tub and game barn.

￥45,227 total

includes taxes & fees

Aug 30 - Aug 31

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

Porter

Tranquil pool barn getaway near Indiana Dunes beckons with heated outdoor pool, hot tub, and refreshing poolside retreat.

￥34,322 total

includes taxes & fees

Aug 11 - Aug 12

7. Country Inn & Suites by Radisson, Portage, IN

Portage

Dive into a refreshing escape with an indoor pool and children's splash area, perfect for family fun in any season.

￥26,474 total

includes taxes & fees

Aug 2 - Aug 3

8. Hampton Inn Portage

Portage

Dive into relaxation at this inviting Portage pool oasis just steps from Indiana Dunes National Park.

￥21,841 total

includes taxes & fees

Aug 30 - Aug 31

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Choose what matters most at hotels with a pool in Chesterton

Breakfast included

Hot tub

Top Chesterton Hotel Reviews

Waterbird Lakeside Inn

8/10 Good

"Clean room Balcony and air conditioning good Staff only saw staff when booking in and out as there was no staff after 5pm Had to ask for clean towels as they were not replenished on a daily basis"

Comfort Inn & Suites Porter near Indiana Dunes

8/10 Good

"My wife and I had a very nice 2 night stay at this hotel. When it comes to evaluating the rooms and conditions, I look to my wife for her opinion since she is much more critical than I am. Her comments were positive and she was satisfied with the cleanliness and comfort of the room and beds. Our room had a single king size bed so there was plenty of room to move about. The room price was reasonable and the breakfast each morning was good as well. The only comment I would have is that this is obviously an older building judging from the exterior color of the building and could probably use some new carpeting in the halls and rooms. Perhaps replacing the carpeting in the rooms with laminate or other similar flooring material would be a better choice. Otherwise our stay was good and we would book again. We chose this location because we wanted to visit Indiana Dunes National Park and it was very convenient to get to the park."

Frequently asked questions

What are some accommodations with pools in Chesterton?

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

What is there to see and do in Chesterton?

Explore places like Indiana Dunes National Park, Lake Michigan, and Indiana Dunes State Park while you're in Chesterton. Surround yourself with nature at Indiana Dunes Visitor Center and Dune Acres Beach. 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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