A wooden staircase ascending a sandy hill with sparse vegetation.

Hotels with Pool & Resorts in Chesterton from AU$114

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Check availability on Chesterton Hotels with Pool

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Chesterton hotels with a pool

An indoor swimming pool with tiled flooring, windows, and a lifeguard chair.
A modern building with large windows and balconies, a wooden deck, and a calm lake.
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.
AU$142
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 spacious room with wooden floors, a large chandelier, and a cozy seating area with sofas and chairs.

2. Spring House Inn

Spring House Inn
Chesterton
  • Relax in the heated indoor pool surrounded by forest views at this tranquil retreat.
AU$165
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 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.

3. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
  • Dive into the sparkling indoor pool oasis, just steps from Indiana Dunes National Park.
AU$173
includes taxes & fees
16 Nov - 17 Nov
Hilton Garden Inn Chesterton
An indoor swimming pool with lounge chairs and a jacuzzi area.
A hotel with a covered entrance, multiple windows, and a parking lot.
A modern kitchen with a coffee station, a bread display, and a refrigerated display.
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 spa pool at this Indiana Dunes retreat.
AU$143
includes taxes & fees
19 Nov - 20 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 beach with sand dunes and grass.
A sandy beach with a wooden staircase leading up a dune, surrounded by greenery.
A bedroom with three beds, each with red and white bedding, a dartboard, and framed pictures on the wall.

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

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Porter
  • Unwind at dual-pool retreat near Indiana Dunes National Park featuring spa pool and game barn.
AU$363
includes taxes & fees
25 Oct - 26 Oct
The "Pool Barn" w/Pool, Hot Tub, Billiards & more 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.

6. 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, spa pool, and refreshing poolside retreat.
AU$240
includes taxes & fees
1 Nov - 2 Nov
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Pool
A hotel room with a bed, a sofa, a desk, and a TV.
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.

7. 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.
AU$237
includes taxes & fees
1 Nov - 2 Nov
Country Inn & Suites by Radisson, Portage, IN
A large indoor swimming pool with clear water, surrounded by lounge chairs and a tiled floor.
A restaurant interior with wooden walls, a bar area, and several tables and chairs.
A reception area with two blue and white reception desks, a grey wall with geometric patterns, and a vending machine in the background.
A hotel room with two beds, a desk, a chair, a TV, and a window with a view of a snowy landscape.

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.
AU$196
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express & Suites Michigan City by IHG
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'.
An outdoor patio area with wicker furniture, a pergola structure, and hanging lamps.
A hotel with a central courtyard, multiple parking levels, and a distinctive architectural style.

9. 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.
AU$147
includes taxes & fees
29 Oct - 30 Oct
Four Winds Casino Resort – New Buffalo
A swimming pool with a sunroof, lounge chairs, and a changing room.
A shower area with a showerhead, handheld shower, and a step stool.
An outdoor patio area with tables and chairs, a building with large windows, and string lights.
A hotel room with a bed, a desk, a chair, and a television.

10. Hampton Inn Portage

Hampton Inn Portage
Portage
  • Dive into relaxation at this inviting Portage pool oasis just steps from Indiana Dunes National Park.
AU$175
includes taxes & fees
31 Oct - 1 Nov
Hampton Inn Portage
View all properties

Choose what matters most at hotels with a pool in Chesterton

Breakfast included
Spa pool
4 stars
5 stars
Spa

Top Chesterton Hotel Reviews

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

10/10 Excellent
"Beautiful property and excellent, attentive staff!"
Steph 1-night trip
Posted 6 hours ago
Blue Chip Casino Hotel and Spa
Spring House Inn

Spring House Inn

8/10 Good
"Unique older hotel in the area of Indiana Dunes NP. The facility has been around for a while...age shows but the bones are good. Modernization would ruin the ambiance! Rooms are huge, clean, and functional. However, they are dimly lit and dated. The hotel is filled with antiques and live plants...a rarity...but they burn candles to mask musty odors...I assume...as there was an odd odor the first day we arrived. Breakfast was the usual hotel fix it your self breakfast. Nothing special but good for included. Parking area could use some sprucing up. I would stay again if in the area."
Sandra 2-night trip
Posted 1 day ago
Spring House Inn
Waterbird Lakeside Inn

Waterbird Lakeside Inn

10/10 Excellent
"Great stay. Reasonable price."
Sandra 2-night trip
Posted 3 days ago
Waterbird Lakeside Inn
Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Very nice room. Lake view was nice. Breakfast was good."
Ruth 1-night trip
Posted 4 days ago
Best Western Indian Oak
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 2 weeks ago
Fairfield Inn and Suites By Marriott Merrillville

Frequently asked questions

What are some accommodation options 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 such as 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 that has an outdoor pool if you're planning to visit Chesterton in the hottest months of July, August or June, when the average temperature is 21°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is 0°C.

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