A wooden staircase ascending a sandy hill with sparse vegetation.

Hotels with Swimming Pools in Chesterton

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Check availability on Chesterton Hotels with Swimming Pools

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Chesterton hotels with a pool

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 wooden deck with a railing overlooking a calm lake at sunset.
A modern building with large windows and balconies, a wooden deck, and a calm lake.

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.
S$122
includes taxes & fees
1 Nov - 2 Nov
Best Western Indian Oak
An indoor swimming pool with clear water, a pool lift, and several tables and chairs around the pool area.
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.
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.

2. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
  • Dive into the sparkling indoor pool oasis, just steps from Indiana Dunes National Park.
S$189
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Chesterton
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 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.

3. Spring House Inn

Spring House Inn
Chesterton
  • Relax in the heated indoor pool surrounded by forest views at this tranquil retreat.
S$148
includes taxes & fees
1 Nov - 2 Nov
Spring House Inn
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.

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.
S$125
includes taxes & fees
9 Nov - 10 Nov
Comfort Inn & Suites Porter near Indiana Dunes
Pool
A hotel room with a bed, a sofa, a desk, and a TV.
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.

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.
S$212
includes taxes & fees
6 Nov - 7 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 hotel room with two beds, a TV, a desk, and a kitchenette.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A trail sign with warnings about wet conditions and closures.

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.
S$179
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express and Suites Portage by IHG
A swimming pool with lounge chairs and a door leading to a covered area.
A modern building with a flat roof, large windows, and a flagpole.
A hotel room with a large bed, a desk with a flat-screen TV, a yellow armchair, and a window with curtains.
A fitness room with a treadmill, elliptical, and stationary bike.

7. Hampton Inn Portage

Hampton Inn Portage
Portage
  • Dive into relaxation at this inviting Portage pool oasis just steps from Indiana Dunes National Park.
S$157
includes taxes & fees
31 Oct - 1 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 hotel room with a large bed, a sitting area with a chair, a bathtub, and a framed picture on the wall.
A hotel lobby with a reception desk, a clock, a blue mat, and a couch.
A living room with leather sofas, a flat-screen TV, and a fireplace.

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.
S$130
includes taxes & fees
1 Nov - 2 Nov
Baymont by Wyndham Portage Indiana Dunes
An indoor swimming pool with blue and green walls, surrounded by various chairs and a lifeguard chair.
A hotel lobby with striped armchairs, a sofa, a dining area, and a kitchenette.
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.

9. 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.
S$102
includes taxes & fees
13 Oct - 14 Oct
Microtel Inn & Suites by Wyndham Michigan City
A hotel with a swimming pool, outdoor seating, and a large building with multiple windows.
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.
A spacious atrium with a stone and wood interior, a sign reading "White Birch Market," and a seating area with chairs.

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.
S$132
includes taxes & fees
12 Oct - 13 Oct
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
"Clean room with great view out the back windows. Great breakfast also."
Ralph 1-night trip
Posted 1 hour ago
Spring House Inn
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

8/10 Good
"Had a great stay the only thing I would be happier about was the water pressure and warmth both in a sap shower. morning and night did not have a very satisfying shower everything else was great!"
Ziah 1-night trip
Posted 6 hours ago
Blue Chip Casino Hotel and Spa
Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Loved the balcony looking out on the small lake behind the hotel. The front desk clerk was nice. Updated bathrooms were nice ecxept ours would not stay closed & had to use a washcoth to hold to closed.Otherwise a very nice stay for going to Indiana Dunes State Park"
Karen 2-night trip
Posted 1 day 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 1 day 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 2 days ago
Hilton Garden Inn Chesterton
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 3 days ago
Holiday Inn Express & Suites New Buffalo by IHG
Microtel Inn & Suites by Wyndham Michigan City

Microtel Inn & Suites by Wyndham Michigan City

10/10 Excellent
"We were very impressed with this hotel. My mom said this was the best hotel that she had stayed at in years. She was really impressed with how brightly lit the room was. There were full size mirrors behind the beds with full length lights behind the beds. They were also recess can lights throughout the room. It smelled clean and fresh. It was absolutely perfect. We would love to stay there again. The breakfast was amazing! Delicious hot eggs, biscuits, gravy, bagels with cream cheese, orange juice and much more. A nice indoor pool. The manager was extremely helpful and friendly. Great place very well maintained!"
Justin 1-night trip
Posted 4 days ago
Microtel Inn & Suites by Wyndham Michigan City
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 5 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 10 days ago
Waterbird Lakeside Inn

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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