A wooden staircase ascending a sandy hill with sparse vegetation.

Find Hotels with a Pool in Chesterton, IN

  • 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 a Pool

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

Our top choices for Chesterton hotels with a pool

A brick building with a balcony and green shutters, surrounded by trees.

1. Spring House Inn

Spring House Inn
2.5 star property
Chesterton
8.8 out of 10, Excellent, (1,001 reviews)
"It was a nice change from the normal big hotels. Small and quaint. Would definitely stay again!!"
United States
Nathaniel
The price is ￥15,598
￥18,258 total
includes taxes & fees
Nov 1 - Nov 2
Spring House Inn
An indoor swimming pool with tiled flooring, windows, and a lifeguard chair.

2. Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1,001 reviews)
"The staff was friendly and room was clean."
United States
Alyssa
The price is ￥14,061
￥15,749 total
includes taxes & fees
Nov 16 - Nov 17
Best Western Indian Oak
A modern bathroom with a large mirror, a bathtub, and a sink.

3. Waterbird Lakeside Inn

Waterbird Lakeside Inn
2.0 star property
Chesterton
8.2 out of 10, Very good, (1,002 reviews)
"Loved the balcony overlooking the lake."
United States
Marsha
The price is ￥14,809
￥16,586 total
includes taxes & fees
Nov 1 - Nov 2
Waterbird Lakeside Inn
A modern dining area with multiple tables and chairs, a kitchen area with blue cabinets, and a reception desk in the background.

4. Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94
2.5 star property
Chesterton
7.8 out of 10, Good, (873 reviews)
"Clean room, friendly staff, easy parking, lots of restaurants and coffee shops in the area."
United States
Nikola
The price is ￥11,919
￥13,349 total
includes taxes & fees
Dec 1 - Dec 2
Quality Inn Chesterton near Indiana Dunes National Park I-94
A hotel lobby with a red carpet, a bookshelf with books, a potted plant, a table with chairs, a small table with a vase, and a door with a red mat.

5. Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton
2.0 star property
Chesterton
6.8 out of 10, (396 reviews)
"Friendly staff great locatikn"
United States
Kayla
The price is ￥11,996
￥13,436 total
includes taxes & fees
Dec 1 - Dec 2
Fairbridge Inn Express Chesterton
A wooden front door with a glass panel, a brick wall, and a small porch with a railing.

6. Furness Mansion

Furness Mansion
2.0 star property
Chesterton
9.0 out of 10, Wonderful, (117 reviews)
"Staff was extremely helpful and responded promptly. The room was very clean, and inviting. Great location for the beaches or short trips to Michigan."
United States
Bryan
The price is ￥19,465
￥21,800 total
includes taxes & fees
Nov 11 - Nov 12
Furness Mansion
An indoor swimming pool with clear water, a pool lift, and several tables and chairs around the pool area.

7. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1,000 reviews)
"Beautiful kept property!"
United States
Renee
The price is ￥15,650
￥17,529 total
includes taxes & fees
Nov 28 - Nov 29
Hilton Garden Inn Chesterton
An indoor swimming pool with lounge chairs and a jacuzzi area.

8. 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)
"Good one night stay. Nice to have breakfast there before we headed out."
United States
Julie Van
The price is ￥13,859
￥15,523 total
includes taxes & fees
Dec 1 - Dec 2
Comfort Inn & Suites Porter near Indiana Dunes
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

Waterbird Lakeside Inn

Waterbird Lakeside Inn

8/10 Good
"Loved the balcony overlooking the lake."
Marsha 1-night trip
Posted 2 days ago
Waterbird Lakeside Inn

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. 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. Comfort Inn & Suites Porter near Indiana Dunes: Offers a snack bar/deli, an indoor pool, and free self parking. Furness Mansion: Hotel steps from Four Winds Casino New Buffalo. Offers 4 restaurants, a seasonal outdoor pool, and 3 bars.
What is there to see and do in Chesterton?
Explore places like 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 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.