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
Sep 4 - Sep 5
Tomorrow
Sep 5 - Sep 6
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Chesterton hotels with a pool

A pool area with a round table and chairs, a tiled floor, and large windows.
A hotel room with a large bed, a separate bathroom with a bathtub, a desk with a chair, and a television.
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.

1. Spring House Inn

Spring House Inn
Chesterton
  • Relax in the heated indoor pool surrounded by forest views at this tranquil retreat.
$97 nightly
$109 total
Oct 1 - Oct 2
Total with taxes and fees
Spring House Inn
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.

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.
$110 nightly
$124 total
Sep 13 - Sep 14
Total with taxes and fees
Best Western Indian Oak
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 spacious lobby with high ceilings, modern lighting fixtures, and potted plants.
A bar area with a long counter, multiple shelves with bottles, and four bar stools.

3. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
  • Dive into the sparkling indoor pool oasis, just steps from Indiana Dunes National Park.
$155 nightly
$174 total
Sep 13 - Sep 14
Total with taxes and fees
Hilton Garden Inn Chesterton
A large house with a swimming pool, a covered patio, and a garage with multiple doors.
A wooden play structure with a slide and a small building.
A beach with sand dunes and grass.
A wooden bridge in a forested area.

4. 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.
$149 nightly
$167 total
Sep 7 - Sep 8
Total with taxes and fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
A large house with a swimming pool, a covered patio, and a garage with multiple doors.
A covered outdoor grill area with a metal roof and a glass enclosure, surrounded by a wooden deck.
A two-story building with a white exterior and a covered porch.
A wooden play structure with a slide and a small building.

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 hot tub and game barn.
$225 nightly
$252 total
Sep 10 - Sep 11
Total with taxes and fees
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
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 reception area with a counter, a vending machine, and a view of the outside through glass doors.
A hotel with a covered entrance, multiple windows, and a parking lot.

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.
$115 nightly
$129 total
Oct 4 - Oct 5
Total with taxes and fees
Comfort Inn & Suites Porter near Indiana Dunes
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.
A hotel room with a bed, a sofa, a desk, and a TV.

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.
$161 nightly
$180 total
Oct 5 - Oct 6
Total with taxes and fees
Country Inn & Suites by Radisson, Portage, IN
A large indoor swimming pool with clear water, surrounded by lounge chairs and a tiled floor.
A bathroom with a white sink, mirror, and toilet. There are towels hanging on the wall and a tissue box on the counter.
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.
$123 nightly
$138 total
Sep 8 - Sep 9
Total with taxes and fees
Holiday Inn Express & Suites Michigan City by IHG
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 multi-story hotel with a prominent "Baymont Inn & Suites" sign.
A hotel lobby with a reception desk, a clock, a blue mat, and a couch.

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.
$89 nightly
$100 total
Sep 20 - Sep 21
Total with taxes and fees
Baymont by Wyndham Portage Indiana Dunes
A swimming pool with three orange chairs and a blue wall with windows.
A modern Hampton Inn & Suites building with a well-lit entrance and a large tree in front.
A modern reception area with a reception desk, a welcome sign, and a large glass door leading outside.
A hotel room with a wooden desk, a flat-screen TV, a chair, a microwave, and a large window.

10. Hampton Inn & Suites Valparaiso

Hampton Inn & Suites Valparaiso
Valparaiso
  • Dive into refreshing aquatic bliss at this airport hotel with an indoor pool and convenient location near local attractions.
$122 nightly
$137 total
Sep 13 - Sep 14
Total with taxes and fees
Hampton Inn & Suites Valparaiso
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

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

8/10 Good
"The room and casino were both satisfactory. Our only complaint is that the hotel tower we were roomed in was a long, long way from the parking lot. You can’t bring your car up close to the exit door."
David 1-night trip
Posted 14 hours ago
Blue Chip Casino Hotel and Spa
Best Western Indian Oak

Best Western Indian Oak

8/10 Good
"Good hot breakfast. Nice patio attached to the room for watching the sunset and listening to the night sounds."
Linda 1-night trip
Posted 2 days ago
Best Western Indian Oak
Quality Inn Near Interstate I94

Quality Inn Near Interstate I94

10/10 Excellent
"No issues at all, except that the check-in process was a bit slow."
Elizabeth 1-night trip
Posted 2 days ago
Quality Inn Near Interstate I94
Spring House Inn

Spring House Inn

10/10 Excellent
"The staff were great. The Continental Breakfast was very good. Our room was nice but needed updated for sure"
Mary 2-night trip
Posted 3 days ago
Spring House 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. Comfort Inn & Suites Porter near Indiana Dunes: Hotel located near Indiana Dunes National Park. Provides daily, an indoor pool, and free self parking. Furness Mansion: Offers a snack bar/deli, an indoor pool, and free self parking. Waterbird Lakeside Inn: 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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