A wooden staircase ascending a sandy hill with sparse vegetation.

Find Hotels with a Pool in Chesterton, IN

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Check availability on Chesterton Hotels with a Pool

Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Chesterton hotels with a pool

A hotel with a swimming pool, outdoor seating, and a large building with multiple windows.
A hotel with a central courtyard, multiple parking levels, and a distinctive architectural style.
The interior of the Four Winds Hotel with a prominent 'Will Call' sign and a large illuminated sign reading 'Alcar Center'.
A spacious atrium with a stone and wood interior, a sign reading "White Birch Market," and a seating area with chairs.

1. Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo
New Buffalo
  • Dive into the seasonal outdoor pool surrounded by loungers, where live music creates a relaxing getaway atmosphere.
$109 nightly
$115 total
Oct 18 - Oct 19
Total with taxes and fees
Four Winds Casino Resort – New Buffalo
An indoor swimming pool with tiled flooring, windows, and a lifeguard chair.
A spacious lobby with multiple seating areas, a staircase, and a large window providing natural light.
A hotel room with a bed, a bathroom with a bathtub, a desk, and a chair.
A wooden deck with a railing overlooking a calm lake at sunset.

2. Best Western Indian Oak

Best Western Indian Oak
Chesterton
  • Discover serene lakeside swimming in a peaceful Indiana Dunes retreat, where the indoor pool welcomes year-round relaxation.
$85 nightly
$95 total
Nov 1 - Nov 2
Total with taxes and fees
Best Western Indian Oak
A pool area with a round table and chairs, a tiled floor, and large windows.
A traditional half-timbered house with multiple balconies, a well-maintained garden, and a clear view of the surrounding greenery.
A spacious dining area with high ceilings and large windows, featuring wooden tables and chairs.
A spacious room with wooden floors, a large chandelier, and a cozy seating area with sofas and chairs.

3. Spring House Inn

Spring House Inn
Chesterton
  • Relax in the heated indoor pool surrounded by forest views at this tranquil retreat.
$103 nightly
$116 total
Nov 1 - Nov 2
Total with taxes and fees
Spring House Inn
A modern hotel with a curved entrance and a tall, rectangular building in the background.
A restaurant interior with a wooden theme, a counter, and seating areas.
A casino interior with gaming tables, chairs, and slot machines.
A hotel room with a large bed, two bedside tables, a chair, a bench, and a large window offering a city view.

4. Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa
Michigan City
  • Splash into pure luxury at this casino hotel with an adults-only indoor pool and 2 hot tubs for post-gaming relaxation.
$116 nightly
$130 total
Oct 18 - Oct 19
Total with taxes and fees
Blue Chip Casino Hotel and Spa
An indoor swimming pool with clear water, a pool lift, and several tables and chairs around the pool area.
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.
A hotel room with a dining area, a sofa, a TV, and a microwave.
A bar area with a long counter, multiple shelves with bottles, and four bar stools.

5. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
  • Dive into the sparkling indoor pool oasis, just steps from Indiana Dunes National Park.
$108 nightly
$120 total
Nov 2 - Nov 3
Total with taxes and fees
Hilton Garden Inn Chesterton
An indoor swimming pool with lounge chairs and a jacuzzi area.
A modern kitchen with a coffee station, a bread display, and a refrigerated display.
A hotel with a covered entrance, multiple windows, and a parking lot.
A reception area with a counter, a vending machine, and a view of the outside through glass doors.

6. Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
Chesterton
  • Splash into relaxation with an indoor pool and rejuvenating hot tub at this Indiana Dunes retreat.
$90 nightly
$101 total
Nov 5 - Nov 6
Total with taxes and fees
Comfort Inn & Suites Porter near Indiana Dunes
A rectangular indoor pool with a tiled edge, surrounded by a stone deck. There are white plastic chairs and a table near a window with a view.
A hotel room with a washing machine, a stack of white towels, and a Tide detergent box.
A hotel room with a large bed, a bathroom with a bathtub, a desk with a chair, and a small table with a lamp.
A gym with treadmills, a wall clock, and a water dispenser.

7. Country Inn & Suites by Radisson, Michigan City, IN

Country Inn & Suites by Radisson, Michigan City, IN
Michigan City
  • Immerse in crystal-clear waters with year-round indoor pool stays near Indiana Dunes.
$115 nightly
$129 total
Nov 8 - Nov 9
Total with taxes and fees
Country Inn & Suites by Radisson, Michigan City, IN
A large indoor swimming pool with clear water, surrounded by lounge chairs and a tiled floor.
A hotel room with two beds, a desk, a chair, a TV, and a window with a view of a snowy landscape.
A reception area with two blue and white reception desks, a grey wall with geometric patterns, and a vending machine in the background.
A restaurant interior with wooden walls, a bar area, and several tables and chairs.

8. Holiday Inn Express & Suites Michigan City by IHG

Holiday Inn Express & Suites Michigan City by IHG
Michigan City
  • Dive into pool bliss with comfy loungers at this sparkling indoor retreat near Indiana Dunes.
$123 nightly
$138 total
Oct 18 - Oct 19
Total with taxes and fees
Holiday Inn Express & Suites Michigan City by IHG
Pool
A modern kitchen with a central island, blue cabinets, and a variety of kitchen appliances.
A multi-story hotel with a covered entrance and stone pillars.
A modern living room with a fireplace, two sofas, a coffee table, and a wooden wall.

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

Country Inn & Suites by Radisson, Portage, IN
Portage
  • Dive into a refreshing escape with an indoor pool and children's splash area, perfect for family fun in any season.
$141 nightly
$158 total
Nov 1 - Nov 2
Total with taxes and fees
Country Inn & Suites by Radisson, Portage, IN
An indoor swimming pool with blue and green walls, surrounded by various chairs and a lifeguard chair.
A bathroom with a granite countertop sink, a mirror, a shower with a curtain, and a towel rack with towels.
A hotel lobby with striped armchairs, a sofa, a dining area, and a kitchenette.
A multi-story hotel with a covered entrance and a brick facade.

10. Microtel Inn & Suites by Wyndham Michigan City

Microtel Inn & Suites by Wyndham Michigan City
Michigan City
  • Dip into poolside bliss at this hotel with loungers, just steps from Michigan beaches.
$71 nightly
$80 total
Oct 18 - Oct 19
Total with taxes and fees
Microtel Inn & Suites by Wyndham Michigan City
View all properties

Choose what matters most at hotels with a pool in Chesterton

Breakfast included
Hot tub
4 stars
5 stars
Beach

Top Chesterton Hotel Reviews

Microtel Inn & Suites by Wyndham Michigan City

Microtel Inn & Suites by Wyndham Michigan City

8/10 Good
"Decent spot for the price. Good staff👍"
Gabriel 1-night trip
Posted less than an hour ago
Microtel Inn & Suites by Wyndham Michigan City
Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"The hotel is clean, comfortable, great location near I94 and good restaurants, serves a good breakfast."
Susan 1-night trip
Posted 7 hours ago
Holiday Inn Express & Suites New Buffalo by IHG
Spring House Inn

Spring House Inn

8/10 Good
"The hotel itself was great for my family of 4. No complaints about the cleanliness or staff. Pool was clean and working, a tad cold, but not a big issue. The only issue i had was with the smell. Walking into the main lobby the strong smell of fragrance greeted me. And the room itself had a perfume smell to it as well. To normal people it may not be a problem, however im highly sensitive to fragrances and often times will get a migraine from strong smells like that. Fortunately I didnt get one while staying there which amazed me. But maybe the hotel can keep in mind that some people do have a sensitivity to fragrance and it may deter them from wanting to stay again."
Amy 1-night trip
Posted 9 hours ago
Spring House Inn
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

10/10 Excellent
"Anytime my wife and I need a little weekend getaway, we are headed to the Blue Chip Casino. The vibe was great. The food at the steakhouse was delicious. The room was top notch."
Joel 1-night trip
Posted 1 day ago
Blue Chip Casino Hotel and Spa
Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

10/10 Excellent
"Well kept property and the staff were friendly. It was very clean."
Nicole 1-night trip
Posted 7 days ago
Comfort Inn & Suites Porter near Indiana Dunes
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

10/10 Excellent
"Hotel was minutes from Indiana state and National Dunes parks. There were two restaurants within walking distance and a gas station across the street. But it was the people at the hotel that made it. And the bartender makes a great margarita. Definitely stay here!"
Michele 1-night trip
Posted 7 days ago
Hilton Garden Inn Chesterton
Fairfield Inn and Suites By Marriott Merrillville

Fairfield Inn and Suites By Marriott Merrillville

10/10 Excellent
"Great experience i had in a long time"
Steve 2-night trip
Posted 10 days ago
Fairfield Inn and Suites By Marriott Merrillville

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.

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