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 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Chesterton hotels with a pool

A hotel with a swimming pool, outdoor seating, and a large building with multiple windows.
The interior of the Four Winds Hotel with a prominent 'Will Call' sign and a large illuminated sign reading 'Alcar Center'.
A hotel with a central courtyard, multiple parking levels, and a distinctive architectural style.
An outdoor patio area with wicker furniture, a pergola structure, and hanging lamps.

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 12 - Oct 13
Total with taxes and fees
Four Winds Casino Resort – New Buffalo
An indoor swimming pool with tiled flooring, windows, and a lifeguard chair.
A hotel room with a bed, a bathroom with a bathtub, a desk, and a chair.
A spacious lobby with multiple seating areas, a staircase, and a large window providing natural light.
A modern building with large windows and balconies, a wooden deck, and a calm lake.

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 spacious room with wooden floors, a large chandelier, and a cozy seating area with sofas and chairs.
A traditional half-timbered house with multiple balconies, a well-maintained garden, and a clear view of the surrounding greenery.
A hotel room with a large bed, a separate bathroom with a bathtub, a desk with a chair, and a television.

3. Spring House Inn

Spring House Inn
Chesterton
  • Relax in the heated indoor pool surrounded by forest views at this tranquil retreat.
$89 nightly
$99 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 reception area with a dark marble counter, wooden paneling, and framed items on the wall.

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 14 - Oct 15
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 a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.
A bar area with a long counter, multiple shelves with bottles, and four bar stools.
A hotel room with a dining area, a sofa, a TV, and a microwave.

5. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
  • Dive into the sparkling indoor pool oasis, just steps from Indiana Dunes National Park.
$134 nightly
$150 total
Oct 25 - Oct 26
Total with taxes and fees
Hilton Garden Inn Chesterton
An indoor swimming pool with lounge chairs and a jacuzzi area.
A hotel room with a large bed, a bedside table with a lamp, a bathroom with a bathtub, and a window with curtains.
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.
$87 nightly
$97 total
Nov 3 - Nov 4
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 large bed, a bathroom with a bathtub, a desk with a chair, and a small table with a lamp.
A hotel room with a washing machine, a stack of white towels, and a Tide detergent box.
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.
$112 nightly
$126 total
Nov 1 - Nov 2
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 restaurant interior with wooden walls, a bar area, and several tables and chairs.
A bathroom with a white sink, a mirror, a toilet, and a towel rack.

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 25 - Oct 26
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.
$148 nightly
$166 total
Oct 14 - Oct 15
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 hotel room with a large bed, a bench by the window, a bedside table with a phone, and a mirror above the bed.
A multi-story hotel with a covered entrance and a brick facade.
A hotel lobby with striped armchairs, a sofa, a dining area, and a kitchenette.

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 11 - Oct 12
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

Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"Extremely nice staff. Most comfortable bed. Breakfast was several steps above most hotels. Different items each day, and warm cinnamon rolls. We used the guest laundry too, which was super convenient. Will definitely stay again!"
Michele 3-night trip
Posted 15 hours ago
Holiday Inn Express & Suites New Buffalo by IHG
Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

8/10 Good
"Good one night stay. Nice to have breakfast there before we headed out."
Julie Van 1-night trip
Posted 18 hours ago
Comfort Inn & Suites Porter near Indiana Dunes
Spring House Inn

Spring House Inn

10/10 Excellent
"Secluded clean place. Dark parking lot, but best to have "lights out" during current ongoing fall bird migration."
rod 1-night trip
Posted 19 hours ago
Spring House Inn
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 2 days ago
Fairfield Inn and Suites By Marriott Merrillville
Waterbird Lakeside Inn

Waterbird Lakeside Inn

8/10 Good
"The room was clean and very comfortable!! And the view was the best!"
Barry 2-night trip
Posted 8 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.

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