TOP Hotels with Pool in Chesterton, IN for 2026

Viewed on an early Spring day, a wooden staircase along a sandy hillside at Indiana Dunes National Park, near Chesterton, IN.

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Our top choices for Chesterton hotels with a pool

Spring House Inn

Chesterton

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

3.934.912 ₫ total

includes taxes & fees

14 Jun - 15 Jun

Hilton Garden Inn Chesterton

Chesterton

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

4.603.161 ₫ total

includes taxes & fees

30 Jun - 1 Jul

Best Western Indian Oak

Chesterton

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

4.126.839 ₫ total

includes taxes & fees

24 Jun - 25 Jun

Comfort Inn & Suites Porter near Indiana Dunes

Chesterton

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

3.182.677 ₫ total

includes taxes & fees

7 Jul - 8 Jul

Seasonal outdoor pool, pool umbrellas, pool 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.

2.995.671 ₫ total

includes taxes & fees

23 Jun - 24 Jun

Quality Inn Near Interstate I94

New Buffalo

Sparkling blue waters await at this forest-surrounded hotel, where relaxation comes with refreshing indoor pool dips.

2.518.130 ₫ total

includes taxes & fees

17 Jun - 18 Jun

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.

3.118.698 ₫ total

includes taxes & fees

28 Jun - 29 Jun

Indoor pool, open 10:00 AM to 11:00 PM, pool loungers

Holiday Inn Express & Suites La Porte by IHG

La Porte

Dive into cool waters at this hotel with an indoor pool and relaxing sun loungers.

3.737.318 ₫ total

includes taxes & fees

21 Jun - 22 Jun

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Breakfast included

Hot tub

Top Chesterton Hotel Reviews

Fairfield Inn & Suites by Marriott Chicago Southeast/Hammond

8/10 Good

"Good property and I would recommend."

Spring House Inn

8/10 Good

"The property gave you that old castle vibe but not the clean version. They had air freshners plugged into the hallway outlets. The carpets need replacing or removal (dirty and stretched out looking). The pool was dirty looking on the bottom and there were particles floating on top. I wanted a room facing the forest area and was told it was first come first serve and those people had selected it, when I went to the hotel website there was no way to select a view or specific room for that matter other than 1 bed or two. When I arrived to my room the balcony doors were unlocked and I wasn't informed. I was on the 1st floor. There were spiderwebs on the balcony. The room areas need more care and there were no chairs on the balcony like in the photos. The property is very beautiful"

Fairfield Inn and Suites By Marriott Merrillville

6/10 Okay

"This has always been my go to for years and years. My last stay the front desk young lady on the night shift was horrible. We were assigned a room that was not cleaned, bed stripped and dirty linen in the chair. When we went back downstairs the front desk person never apologized or acknowledged our dismay. I provided her the picture as well. We now stay with a competitor."

Best Western Indian Oak

10/10 Excellent

"For the cost and convenience to the beach, we really enjoyed our stay here! We stayed midweek, so it was quiet and relaxing with very few people at the pool or around the property. The rooms were some of the largest we’ve ever had at a hotel like this, which made our stay even more comfortable. One of the best parts was the view—it truly felt like we were right on the water, and the scenery was absolutely amazing. The location made it easy to enjoy the beaches while still having a peaceful place to unwind. Another bonus was how convenient everything was. There were plenty of fast-food restaurants and grocery stores within walking distance, which added a lot of value and made our stay even easier. We would definitely recommend staying here and would love to come back again!"

Frequently asked questions

What is there to see and do in Chesterton?

Explore places such as Lake Michigan and Indiana Dunes National 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 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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Treat yourself

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Check availability on Chesterton Hotels with Pool

Our top choices for Chesterton hotels with a pool

Spring House Inn

Hilton Garden Inn Chesterton

Best Western Indian Oak

Comfort Inn & Suites Porter near Indiana Dunes

Four Winds Casino Resort – New Buffalo

Quality Inn Near Interstate I94

Hampton Inn & Suites Michigan City

Holiday Inn Express & Suites La Porte by IHG

The Blue Heron Inn

Choose what matters most at hotels with a pool in Chesterton

Top Chesterton Hotel Reviews

Fairfield Inn & Suites by Marriott Chicago Southeast/Hammond

Spring House Inn

Blue Chip Casino Hotel and Spa

Comfort Inn & Suites Porter near Indiana Dunes

Waterbird Lakeside Inn

Country Inn & Suites by Radisson, Merrillville, IN

Fairfield Inn and Suites By Marriott Merrillville

Best Western Indian Oak

Quality Inn Near Interstate I94

Frequently asked questions

Explore a world of travel with Expedia

Search Hotels with Pool in Chesterton

Change your mind

Treat yourself

Be picky

Check availability on Chesterton Hotels with Pool

Our top choices for Chesterton hotels with a pool

Spring House Inn

Hilton Garden Inn Chesterton

Best Western Indian Oak

Comfort Inn & Suites Porter near Indiana Dunes

Four Winds Casino Resort – New Buffalo

Quality Inn Near Interstate I94

Hampton Inn & Suites Michigan City

Holiday Inn Express & Suites La Porte by IHG

The Blue Heron Inn

Choose what matters most at hotels with a pool in Chesterton

Top Chesterton Hotel Reviews

Fairfield Inn & Suites by Marriott Chicago Southeast/Hammond

Frequently asked questions

Explore a world of travel with Expedia