TOP Hotels with Swimming Pool in Chesterton, IN for 2026

Q: What are some accommodation options with pools in Chesterton?

Comfort Inn & Suites Porter near Indiana Dunes : Hotel located near Indiana Dunes National Park. Features daily, 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 : Hotel located near Indiana Dunes National Park. Features a sauna, an indoor pool and free self parking. Best Western Indian Oak : Offers a snack bar/deli, an indoor pool and free self parking. Hilton Garden Inn Chesterton : Features complimentary wireless Internet access, a pool and kitchens.

Lake Michigan. Path off Trail 9 at one place leads right to the lake. Peaceful to just stand and watch and listen to the waves as they crash to the shore. Trail 9 is the trail to hike if one wants to see the most in the shortest time. Great views throughout the trail. The trail is over 3 miles long and is considered a moderate trail. But certainly worth it. One gets to hike through forest, dunes, and other natural environments and see such a variety of sights.
#hiking

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 Swimming Pool

Tonight

Tomorrow

This weekend

Next weekend

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.

₹9,605 total

includes taxes & fees

10 Mar - 11 Mar

Comfort Inn & Suites Porter near Indiana Dunes

Chesterton

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

₹8,324 total

includes taxes & fees

12 Mar - 13 Mar

Best Western Indian Oak

Chesterton

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

₹8,631 total

includes taxes & fees

15 Mar - 16 Mar

Hilton Garden Inn Chesterton

Chesterton

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

₹11,123 total

includes taxes & fees

29 Mar - 30 Mar

Super 8 by Wyndham Valparaiso

Valparaiso

Dive into year-round swim sessions at this hotel's inviting indoor heated pool.

₹7,512 total

includes taxes & fees

16 Mar - 17 Mar

Indoor pool, open 9:00 AM to 10:00 PM, pool loungers

Microtel Inn & Suites by Wyndham Michigan City

Michigan City

Dip into poolside bliss at this hotel with loungers, just steps from Michigan beaches.

₹6,657 total

includes taxes & fees

18 Mar - 19 Mar

Hampton Inn & Suites Valparaiso

Valparaiso

Dive into refreshing aquatic bliss at this airport hotel with an indoor pool and convenient location near local attractions.

₹11,084 total

includes taxes & fees

4 Apr - 5 Apr

Quality Inn Michigan City South

Michigan City

Dive into year-round aquatic bliss at this Michigan City hotel featuring an indoor pool just steps from shopping and casinos.

₹7,306 total

includes taxes & fees

16 Mar - 17 Mar

View all properties

Choose what matters most at hotels with a pool in Chesterton

Breakfast included

Hot tub

Top Chesterton Hotel Reviews

Hilton Garden Inn Chesterton

10/10 Excellent

" T"

Waterbird Lakeside Inn

10/10 Excellent

"We were pleasantly surprised by our room. The floors were clean. The bed was clean. Everything smelled good even in the hallway. There were no noisy neighbors and the balcony overlooking the water was peaceful and beautiful. We loved getting visits from the geese and the beautiful swan. I would absolutely stay there again."

Comfort Inn & Suites Porter near Indiana Dunes

6/10 Okay

"Staff gave us a nice quiet room .. thanks so much! Breakfast left a lot to be desired. No yogurt variety.. no oatmeal variety.. rolls were dry.. no fruit variety.. no meat or egg variety.. pretty blah.. kids had taken over pool we couldn’t get in.."

Frequently asked questions

What are some accommodation options with pools in Chesterton?

Comfort Inn & Suites Porter near Indiana Dunes: Hotel located near Indiana Dunes National Park. Features daily, 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: Hotel located near Indiana Dunes National Park. Features a sauna, an indoor pool and free self parking. Best Western Indian Oak: Offers a snack bar/deli, an indoor pool and free self parking. Hilton Garden Inn Chesterton: Features complimentary wireless Internet access, a pool and kitchens.

What is there to see and do in Chesterton?

Explore places such as Indiana Dunes National Park and Lake Michigan while you're in Chesterton. Surround yourself with nature at Indiana Dunes Visitor Center and Coffee Creek Watershed Conservancy Preserve. 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.

Explore a world of travel with Expedia

More ways to book

Book Hotels with Swimming Pool in Chesterton on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Chesterton Hotels with Swimming Pool