A wooden staircase ascending a sandy hill with sparse vegetation.

Search Hotels with Pool in Chesterton

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Chesterton Hotels with Pool

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Chesterton hotels with a pool

A pool area with a round table and chairs, a tiled floor, and large windows.

1. Spring House Inn

Spring House Inn
2.5 star property
Chesterton
8.8 out of 10, Excellent, (1,022 reviews)
  • cleanliness
    Relax in the heated indoor pool surrounded by forest views at this tranquil retreat.
The price is 2.557.566 ₫
2.993.644 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Spring House Inn
An indoor swimming pool with clear water, a pool lift, and several tables and chairs around the pool area.

2. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1,007 reviews)
  • cleanliness
    Dive into the sparkling indoor pool oasis, just steps from Indiana Dunes National Park.
The price is 2.626.801 ₫
2.942.017 ₫ total
includes taxes & fees
28 Nov - 29 Nov
Hilton Garden Inn Chesterton
An indoor swimming pool with tiled flooring, windows, and a lifeguard chair.

3. Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Discover serene lakeside swimming in a peaceful Indiana Dunes retreat, where the indoor pool welcomes year-round relaxation.
The price is 2.305.426 ₫
2.582.077 ₫ total
includes taxes & fees
4 Nov - 5 Nov
Best Western Indian Oak
An indoor swimming pool with lounge chairs and a jacuzzi area.

4. Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
2.5 star property
Chesterton
7.8 out of 10, Good, (1,000 reviews)
  • cleanliness
    Splash into relaxation with an indoor pool and rejuvenating hot tub at this Indiana Dunes retreat.
The price is 2.326.093 ₫
2.605.225 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Comfort Inn & Suites Porter near Indiana Dunes
Pool

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

Country Inn & Suites by Radisson, Portage, IN
3.0 star property
Portage
8.4 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Dive into a refreshing escape with an indoor pool and children's splash area, perfect for family fun in any season.
The price is 3.267.743 ₫
3.659.871 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Country Inn & Suites by Radisson, Portage, IN
An indoor swimming pool with clear water, marked depth lines, and lounge chairs around the perimeter.

6. Holiday Inn Express and Suites Portage by IHG

Holiday Inn Express and Suites Portage by IHG
2.5 star property
Portage
8.4 out of 10, Very good, (656 reviews)
  • cleanliness
    Escape into a refreshing indoor pool sanctuary with loungers where every swim feels like a tranquil retreat from everyday life.
The price is 3.100.080 ₫
3.610.302 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express and Suites Portage by IHG
A hotel with a swimming pool, outdoor seating, and a large building with multiple windows.

7. Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo
3.5 star property
New Buffalo
9.4 out of 10, Exceptional, (2,310 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool surrounded by loungers, where live music creates a relaxing getaway atmosphere.
The price is 2.301.809 ₫
2.670.202 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Four Winds Casino Resort – New Buffalo
A swimming pool with lounge chairs and a door leading to a covered area.

8. Hampton Inn Portage

Hampton Inn Portage
2.5 star property
Portage
8.6 out of 10, Excellent, (95 reviews)
  • cleanliness
    Dive into relaxation at this inviting Portage pool oasis just steps from Indiana Dunes National Park.
The price is 2.832.698 ₫
3.172.622 ₫ total
includes taxes & fees
27 Nov - 28 Nov
Hampton Inn Portage
A pool area with chairs and tables, a sign indicating the pool is for guest use only, and a door leading to another room.

9. Baymont by Wyndham Portage Indiana Dunes

Baymont by Wyndham Portage Indiana Dunes
2.5 star property
Portage
7.0 out of 10, Good, (1,004 reviews)
  • cleanliness
    Dive into comfort at this Indiana Dunes hotel with an indoor pool that's perfect for all-season splashing.
The price is 2.336.944 ₫
2.617.377 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Baymont by Wyndham Portage Indiana Dunes
An indoor swimming pool with white chairs and tables, a 'No Diving' sign, and 'Pool Rules' posted on the wall.

10. Quality Inn Michigan City South

Quality Inn Michigan City South
2.5 star property
Michigan City
7.4 out of 10, Good, (1,007 reviews)
  • cleanliness
    Dive into year-round aquatic bliss at this Michigan City hotel featuring an indoor pool just steps from shopping and casinos.
The price is 2.040.886 ₫
2.285.792 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Quality Inn Michigan City South
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.
View all properties

Choose what matters most at hotels with a pool in Chesterton

Breakfast included
Hot tub

Top Chesterton Hotel Reviews

Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"No issue at all will stay here again"
Melissa 2-night trip
Posted 2 days ago
Holiday Inn Express & Suites New Buffalo by IHG

Frequently asked questions

What is there to see and do in Chesterton?
Explore places such as 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 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.