The Best Hotels with a Pool in Chesterton, IN from AED 323 in 2026 | Expedia

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

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Check availability on Chesterton Hotels with a Pool

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25 Jan - 26 Jan

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26 Jan - 27 Jan

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Our top choices for Chesterton hotels with a pool

Indoor pool

Spring House Inn

Chesterton

United States

Joseph

AED 343 total

includes taxes & fees

26 Jan - 27 Jan

Indoor pool

Best Western Indian Oak

Chesterton

United States

Dmytro

AED 367 total

includes taxes & fees

31 Jan - 1 Feb

Indoor pool

Hilton Garden Inn Chesterton

Chesterton

United States

Tim

AED 401 total

includes taxes & fees

1 Feb - 2 Feb

Indoor spa tub

Comfort Inn & Suites Porter near Indiana Dunes

Chesterton

United States

Alison

AED 330 total

includes taxes & fees

1 Feb - 2 Feb

Outdoor pool, a heated pool

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

Porter

"Every aspect of my booking & stay was convenient & seamless; from the reasonable price, online reservation process, host communication, beautiful grounds, to the abundant amenities offered there was nothing I or my family wanted for. Don & Kim are accommodating, professional & experienced hosts and it showed. Thank you for the wonderful experience I recommend their multiple spaces to anyone & would stay with them again without hesitation! "

United States

esther Amber C.

AED 323 total

includes taxes & fees

26 Jan - 27 Jan

Outdoor pool, a heated pool

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

Porter

United States

Jane H.

AED 940 total

includes taxes & fees

26 Jan - 27 Jan

Seasonal outdoor pool, pool umbrellas, sun loungers

Four Winds Casino Resort – New Buffalo

New Buffalo

United States

Benjamin

AED 359 total

includes taxes & fees

26 Jan - 27 Jan

Indoor pool

Blue Chip Casino Hotel and Spa

Michigan City

United States

Joe

AED 420 total

includes taxes & fees

29 Jan - 30 Jan

View all properties

Choose what matters most at hotels with a pool in Chesterton

Hot tub

Beach

Top Chesterton Hotel Reviews

Fairfield Inn & Suites by Marriott Chicago Southeast/Hammond

Fairfield Inn & Suites by Marriott Chicago Southeast/Hammond

10/10 Excellent

"Awesome and comforting stay"

Spring House Inn

Spring House Inn

10/10 Excellent

"Although off the beaten path it’s in a beautiful location. The room was clean and spacious with a small balcony. The young men running the front desk were so nice and helpful. The continental breakfast had a little bit of everything. There’s a nice pool area, numerous seating areas to sit and visit with the people you are with, and a restaurant/bar at the end of the parking lot! Looking forward to staying here in the summer and enjoying the beach/dunes/state park!"

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Frequently asked questions

What are some accommodations 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: Features a snack bar/deli, an indoor pool, and free self parking. Hilton Garden Inn Chesterton: Hotel located near Indiana Dunes National Park. Offers a sauna, an indoor pool, and free self parking. Best Western Indian Oak: Hotel steps from Blue Chip Casino. Provides 3 restaurants, an indoor pool, and a full-service spa.

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 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 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.

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