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 26 - Sep 27
Tomorrow
Sep 27 - Sep 28
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

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 4 - Oct 5
Total with taxes and fees
Spring House Inn
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.

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
Oct 5 - Oct 6
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 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 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.
$153 nightly
$171 total
Oct 26 - Oct 27
Total with taxes and fees
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 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.

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.
$106 nightly
$118 total
Oct 18 - Oct 19
Total with taxes and fees
Comfort Inn & Suites Porter near Indiana Dunes
A large house with a swimming pool, a covered patio, and a garage with multiple doors.
A two-story building with a white exterior and a covered porch.
A wooden play structure with a slide and a small building.
A covered outdoor grill area with a metal roof and a glass enclosure, surrounded by a wooden deck.

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.
$219 nightly
$245 total
Sep 27 - Sep 28
Total with taxes and fees
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 fire pit surrounded by wooden benches and chairs in an outdoor setting.
A beach with sand dunes and grass.
A wooden bridge in a forested area.

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, hot tub, and refreshing poolside retreat.
$149 nightly
$167 total
Sep 28 - Sep 29
Total with taxes and fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
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.

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.
$148 nightly
$166 total
Oct 8 - Oct 9
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 restaurant interior with wooden walls, a bar area, and several tables and chairs.
A hotel room with two beds, a desk, a chair, a TV, and a window with a view of a snowy landscape.
A bathroom with a white sink, a mirror, a toilet, and a towel rack.

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
Oct 4 - Oct 5
Total with taxes and fees
Holiday Inn Express & Suites Michigan City by IHG
An indoor swimming pool with blue and green walls, surrounded by various chairs and a lifeguard chair.
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 bathroom with a granite countertop sink, a mirror, a shower with a curtain, and a towel rack with towels.
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.
$71 nightly
$80 total
Sep 30 - Oct 1
Total with taxes and fees
Microtel Inn & Suites by Wyndham Michigan City
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 multi-story hotel with a prominent "Baymont Inn & Suites" sign.
A living room with leather sofas, a flat-screen TV, and a fireplace.
A hotel lobby with a reception desk, a clock, a blue mat, and a couch.

10. 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.
$90 nightly
$101 total
Oct 18 - Oct 19
Total with taxes and fees
Baymont by Wyndham Portage Indiana Dunes
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

Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

8/10 Good
"Room could have been a little cleaner but everything was good"
Robert 2-night trip
Posted 1 hour ago
Comfort Inn & Suites Porter near Indiana Dunes
Spring House Inn

Spring House Inn

8/10 Good
"Overall nice stay. Large room with great view at back forest. Price a little high as room and hotel a little worn. Great location for Indiana Dunes NP exploration."
Mark 1-night trip
Posted 20 hours ago
Spring House Inn
Comfort Inn Hammond I-94

Comfort Inn Hammond I-94

8/10 Good
"Very clean. Good place for a crash and dash we did not get a chance to check out the breakfast as it ended at nine."
Ron 1-night trip
Posted 1 day ago
Comfort Inn Hammond I-94
Fairfield Inn and Suites By Marriott Merrillville

Fairfield Inn and Suites By Marriott Merrillville

8/10 Good
"Everything was fine, but the hotel is showing some age and needs some improvements."
annie 1-night trip
Posted 2 days ago
Fairfield Inn and Suites By Marriott Merrillville
Waterbird Lakeside Inn

Waterbird Lakeside Inn

10/10 Excellent
"I arrived at the hotel after being discharged from a local hospital. I was traveling from NY to Colorado by motorcycle when I was hit by a truck. After 2 days in the hospital, I booked this hotel to recover, treat my wounds and wait for my motorcycle to be inspected. I ended up staying at Waterbird for 6 nights. The staff was amazing. So kind, caring and helpful. My room was quite large, comfortable and clean. The private lakeside deck was the perfect spot to drink morning coffee and relax while my wounds started to heal. Thank you so much, Missy and Max at the front desk. Thank you to Christina, Jessica, and Tracy, the housekeepers who made sure I had what I needed each day. I am truly grateful."
Dina 1-night trip
Posted 4 days ago
Waterbird Lakeside 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. Quality Inn Chesterton near Indiana Dunes National Park I-94: 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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