A wooden staircase ascending a sandy hill with sparse vegetation.

Hotels with Swimming Pool in Chesterton, Indiana

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Check availability on Chesterton Hotels with Swimming Pool

Tonight
Oct 25 - Oct 26
Tomorrow
Oct 26 - Oct 27
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Our top choices for Chesterton hotels with a pool

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 spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.
A hotel room with a dining area, a sofa, a TV, and a microwave.

1. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
  • Dive into the sparkling indoor pool oasis, just steps from Indiana Dunes National Park.
P6,884
P7,710 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Chesterton
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 modern building with large windows and balconies, a wooden deck, and a calm lake.
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.
P5,676
P6,357 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Indian Oak
A pool area with a round table and chairs, a tiled floor, and large windows.
A spacious dining area with high ceilings and large windows, featuring wooden tables and chairs.
A traditional half-timbered house with multiple balconies, a well-maintained garden, and a clear view of the surrounding greenery.
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.
P6,296
P7,370 total
includes taxes & fees
Nov 1 - Nov 2
Spring House Inn
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.

4. 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.
P5,726
P6,414 total
includes taxes & fees
Nov 22 - Nov 23
Comfort Inn & Suites Porter near Indiana Dunes
Pool
A modern living room with a fireplace, two sofas, a coffee table, and a wooden wall.
A multi-story hotel with a covered entrance and stone pillars.
A modern kitchen with a central island, blue cabinets, and a variety of kitchen appliances.

5. 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.
P7,956
P8,911 total
includes taxes & fees
Nov 1 - Nov 2
Country Inn & Suites by Radisson, Portage, IN
An indoor swimming pool with clear water, marked depth lines, and lounge chairs around the perimeter.
A Holiday Inn Express & Suites building with a covered entrance and a gravel driveway.
A hotel room with two beds, a desk with a computer, a TV, and a large window.
A hotel lobby with a reception desk, seating area, and a bar.

6. Holiday Inn Express and Suites Portage by IHG

Holiday Inn Express and Suites Portage by IHG
Portage
  • Escape into a refreshing indoor pool sanctuary with loungers where every swim feels like a tranquil retreat from everyday life.
P7,632
P8,888 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Express and Suites Portage by IHG
A swimming pool with lounge chairs and a door leading to a covered area.
A hotel reception area with a modern design, featuring a reception desk with a wooden accent, a 'Welcome to the Hoosier State' sign, and a 'Hilton Honors' sign.
A hotel room with two beds, a flat-screen TV, a desk with a lamp, and a window with curtains.
A modern bathroom with a toilet, sink, and mirror.

7. Hampton Inn Portage

Hampton Inn Portage
Portage
  • Dive into relaxation at this inviting Portage pool oasis just steps from Indiana Dunes National Park.
P6,974
P7,810 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Portage
A pool area with chairs and tables, a sign indicating the pool is for guest use only, and a door leading to another room.
A hotel room with a large bed, a sitting area with a chair, a bathtub, and a framed picture on the wall.
A living room with leather sofas, a flat-screen TV, and a fireplace.
A multi-story hotel with a prominent "Baymont Inn & Suites" sign.

8. Baymont by Wyndham Portage Indiana Dunes

Baymont by Wyndham Portage Indiana Dunes
Portage
  • Dive into comfort at this Indiana Dunes hotel with an indoor pool that's perfect for all-season splashing.
P5,753
P6,444 total
includes taxes & fees
Nov 9 - Nov 10
Baymont by Wyndham Portage Indiana Dunes
A modern building with stone exterior walls, large windows, and outdoor seating area with chairs and a small tree.
A Hampton Inn & Suites hotel with a modern design, featuring a covered entrance, stone facade, and multiple flags including the American flag and the European Union flag.
A spacious lobby with a high ceiling, a central dining area, and comfortable seating arrangements.
A hotel room with a bed, desk, chair, kitchenette, and a painting on the wall.

9. Hampton Inn & Suites Michigan City

Hampton Inn & Suites Michigan City
Michigan City
  • Dive into refreshing relaxation at this Michigan City hotel with a spotless indoor pool and daily complimentary breakfast buffet.
P7,249
P8,119 total
includes taxes & fees
Nov 22 - Nov 23
Hampton Inn & Suites Michigan City
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 spacious atrium with a stone and wood interior, a sign reading "White Birch Market," and a seating area with chairs.
A hotel with a central courtyard, multiple parking levels, and a distinctive architectural style.

10. 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.
P5,667
P6,574 total
includes taxes & fees
Oct 26 - Oct 27
Four Winds Casino Resort – New Buffalo
View all properties

Choose what matters most at hotels with a pool in Chesterton

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Chesterton Hotel Reviews

Spring House Inn

Spring House Inn

10/10 Excellent
"The Inn had an old world charm to it. It was dated, but in the best way. Everything was very clean, even the bathroom. The breakfast was above par, with a couple of hot food options. The bed was very comfy, the room was spacious and plenty of seating. Lake Michigan was very close, just a five minute drive. Plenty of parking at the Dunes National Park. We didn't use the pool, but the kids at the hotel seemed to love it. The price is great and the rooms clean and comfortable. If you want something other than the chain hotels, this just might be the place for you."
Sherrie 1-night trip
Posted 1 day ago
Spring House Inn
Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"The room was very clean. We stayed 2 days. Enjoyed the breakfast. The staff was always nice!"
Joan 2-night trip
Posted 2 days ago
Best Western Indian Oak
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

10/10 Excellent
"Beautiful kept property!"
Renee 1-night trip
Posted 2 days ago
Hilton Garden Inn Chesterton
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 2 weeks ago
Comfort Inn & Suites Porter near Indiana Dunes
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 3 weeks 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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