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

Hotels with Swimming Pool in Chesterton, Indiana

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Chesterton Hotels with Swimming Pool

Our top choices for Chesterton hotels with a pool

Spring House Inn

Spring House Inn
2.5 star property
Chesterton
9.0 out of 10, Wonderful, (1,012 reviews)
  • cleanliness
    Relax in the heated indoor pool surrounded by forest views at this tranquil retreat.
The price is P7,923
P9,181 total
includes taxes & fees
Jun 15 - Jun 16
Spring House Inn

Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1,009 reviews)
  • cleanliness
    Discover serene lakeside swimming in a peaceful Indiana Dunes retreat, where the indoor pool welcomes year-round relaxation.
The price is P8,598
P9,630 total
includes taxes & fees
Jun 15 - Jun 16
Best Western Indian Oak

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1,006 reviews)
  • cleanliness
    Dive into the sparkling indoor pool oasis, just steps from Indiana Dunes National Park.
The price is P9,007
P10,088 total
includes taxes & fees
Jun 29 - Jun 30
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, (1,005 reviews)
  • cleanliness
    Splash into relaxation with an indoor pool and rejuvenating hot tub at this Indiana Dunes retreat.
The price is P6,637
P7,433 total
includes taxes & fees
Jul 9 - Jul 10
Comfort Inn & Suites Porter near Indiana Dunes

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo
3.5 star property
New Buffalo
9.4 out of 10, Exceptional, (1,906 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool surrounded by loungers, where live music creates a relaxing getaway atmosphere.
The price is P5,484
P6,362 total
includes taxes & fees
Jun 23 - Jun 24
Four Winds Casino Resort – New Buffalo

Hampton Inn & Suites Michigan City

Hampton Inn & Suites Michigan City
2.5 star property
Michigan City
8.6 out of 10, Excellent, (975 reviews)
  • cleanliness
    Dive into refreshing relaxation at this Michigan City hotel with a spotless indoor pool and daily complimentary breakfast buffet.
The price is P7,289
P8,164 total
includes taxes & fees
Jun 21 - Jun 22
Hampton Inn & Suites Michigan City

The Blue Heron Inn

The Blue Heron Inn
3.0 star property
La Porte
9.0 out of 10, Wonderful, (572 reviews)
  • cleanliness
    Lakeside pool oasis comes alive with sunsets, boat rentals, and creature comforts by Pine Lake.
The price is P7,984
P8,942 total
includes taxes & fees
Jun 21 - Jun 22
The Blue Heron Inn

Quality Inn Near Interstate I94

Quality Inn Near Interstate I94
2.5 star property
New Buffalo
8.4 out of 10, Very Good, (1,197 reviews)
  • cleanliness
    Sparkling blue waters await at this forest-surrounded hotel, where relaxation comes with refreshing indoor pool dips.
The price is P5,543
P5,876 total
includes taxes & fees
Jun 21 - Jun 22
Quality Inn Near Interstate I94

Fairfield Inn & Suites by Marriott New Buffalo

Fairfield Inn & Suites by Marriott New Buffalo
3.0 star property
New Buffalo
8.4 out of 10, Very Good, (1,006 reviews)
  • cleanliness
    Splash into indoor poolside fun just moments from Lake Michigan's shores.
The price is P9,151
P9,700 total
includes taxes & fees
Jun 17 - Jun 18
Fairfield Inn & Suites by Marriott New Buffalo
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.

Choose what matters most at hotels with a pool in Chesterton

Top Chesterton Hotel Reviews

Frequently asked questions

What are some accommodations with pools in Chesterton?
Best Western Indian Oak: Hotel located near Indiana Dunes National Park. Features a sauna, 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. Waterbird Lakeside Inn: Features a snack bar/deli, an indoor pool, and free self parking. Hilton Garden Inn Chesterton: Hotel located near Indiana Dunes National Park. Features daily, an indoor pool, and free self parking. Furness Mansion: Features complimentary wireless internet access, a pool, and kitchens.
What is there to see and do in Chesterton?
Explore places like 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 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.

Explore a world of travel with Expedia