A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Hotels with a Pool

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Chesterton hotels with a pool

An indoor swimming pool with tiled flooring, windows, and a lifeguard chair.
A wooden deck with a railing overlooking a calm lake at sunset.
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.

1. 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.
AED 328
AED 367 total
includes taxes & fees
1 Nov - 2 Nov
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 hotel room with a large bed, a separate bathroom with a bathtub, a desk with a chair, and a television.

2. Spring House Inn

Spring House Inn
Chesterton
  • Relax in the heated indoor pool surrounded by forest views at this tranquil retreat.
AED 364
AED 426 total
includes taxes & fees
1 Nov - 2 Nov
Spring House Inn
An indoor swimming pool with clear water, a pool lift, and several tables and chairs around the pool area.
A hotel room with a dining area, a sofa, a TV, and a microwave.
A spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.

3. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
  • Dive into the sparkling indoor pool oasis, just steps from Indiana Dunes National Park.
AED 392
AED 439 total
includes taxes & fees
1 Nov - 2 Nov
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 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.

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.
AED 331
AED 370 total
includes taxes & fees
22 Nov - 23 Nov
Comfort Inn & Suites Porter near Indiana Dunes
A large house with a swimming pool, a covered patio, and a garage with multiple doors.
A wooden bridge in a forested area.
A wooden play structure with a slide and a small building.
A fire pit surrounded by wooden benches and chairs in an outdoor setting.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
  • Tranquil pool barn getaway near Indiana Dunes beckons with heated outdoor pool, hot tub, and refreshing poolside retreat.
AED 474
AED 613 total
includes taxes & fees
8 Nov - 9 Nov
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
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 hotel room with a bed, a sofa, a desk, and a TV.

6. 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.
AED 459
AED 515 total
includes taxes & fees
1 Nov - 2 Nov
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 breakfast area with a buffet setup, including hot food and cereal options.

7. 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.
AED 441
AED 513 total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express and Suites Portage by IHG
A swimming pool with lounge chairs and a door leading to a covered area.
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.
Exterior

8. Hampton Inn Portage

Hampton Inn Portage
Portage
  • Dive into relaxation at this inviting Portage pool oasis just steps from Indiana Dunes National Park.
AED 434
AED 486 total
includes taxes & fees
2 Nov - 3 Nov
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 living room with leather sofas, a flat-screen TV, and a fireplace.
A hotel room with a large bed, a sitting area with a chair, a bathtub, and a framed picture on the wall.
A multi-story hotel with a prominent "Baymont Inn & Suites" sign.

9. 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.
AED 332
AED 372 total
includes taxes & fees
9 Nov - 10 Nov
Baymont by Wyndham Portage Indiana Dunes
An indoor swimming pool with white chairs and tables, a 'No Diving' sign, and 'Pool Rules' posted on the wall.
A bathroom with a bathtub, toilet, sink, and a large mirror.
A sandy beach with a wooden fence leading to the water.
A hotel room with two beds, a sitting area with a chair, a small table, a kitchenette, and a bathroom.

10. Quality Inn Michigan City South

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.
AED 292
AED 327 total
includes taxes & fees
28 Oct - 29 Oct
Quality Inn Michigan City South
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

Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Room was clean. Was in town for a wedding and it was close to the venue. Nice spot."
Julissa 2-night trip
Posted 12 hours ago
Best Western Indian Oak
Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"Nice stay; even though the hot tub wasn’t working properly."
Shawn 1-night trip
Posted 14 hours ago
Holiday Inn Express & Suites New Buffalo by IHG
Spring House Inn

Spring House Inn

8/10 Good
"Staff was great and the property had a unique lodge type feel. It was also very close to the Indiana Dunes National and State parks. Only downside is that it desperately needs some maintenance and updating."
Noelle 2-night trip
Posted 14 hours ago
Spring House Inn
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

8/10 Good
"Beautiful room! No microwave and pool was out of service, but still charged a resort fee.. otherwise a great stay."
Olivia 1-night trip
Posted 16 hours 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 3 weeks ago
Comfort Inn & Suites Porter near Indiana Dunes

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.