A wooden staircase ascending a sandy hill with sparse vegetation.

Search Hotels with Pool in Chesterton

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Check availability on Chesterton Hotels with Pool

Tonight
10 Sep - 11 Sep
Tomorrow
11 Sep - 12 Sep
This weekend
11 Sep - 13 Sep
Next weekend
18 Sep - 20 Sep

Our top choices for Chesterton hotels with a pool

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.
฿3,636
฿4,072 total
includes taxes & fees
16 Sept - 17 Sept
Best Western Indian Oak

2. Spring House Inn

Spring House Inn
Chesterton
  • Relax in the heated indoor pool surrounded by forest views at this tranquil retreat.
฿2,690
฿3,177 total
includes taxes & fees
1 Oct - 2 Oct
Spring House Inn

3. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
  • Dive into the sparkling indoor pool oasis, just steps from Indiana Dunes National Park.
฿4,830
฿5,410 total
includes taxes & fees
20 Sept - 21 Sept
Hilton Garden Inn Chesterton

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.
฿3,751
฿4,201 total
includes taxes & fees
30 Sept - 1 Oct
Comfort Inn & Suites Porter near Indiana Dunes

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.
฿4,335
฿4,856 total
includes taxes & fees
27 Sept - 28 Sept
Country Inn & Suites by Radisson, Portage, IN

6. 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.
฿3,883
฿4,525 total
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn Express & Suites Michigan City by IHG

7. 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.
฿2,977
฿3,334 total
includes taxes & fees
27 Sept - 28 Sept
Baymont by Wyndham Portage Indiana Dunes

8. 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.
฿2,349
฿2,631 total
includes taxes & fees
14 Sept - 15 Sept
Microtel Inn & Suites by Wyndham Michigan City
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

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

10/10 Excellent
"It was my first time only thing that it wasn’t a microwave in the room everything was Nice"
Denise 1-night trip
Posted 4 hours ago
Blue Chip Casino Hotel and Spa
Microtel Inn & Suites by Wyndham Michigan City

Microtel Inn & Suites by Wyndham Michigan City

8/10 Good
"Good enough for stay. Breakfast is sufficient. The pool unfortunately is not available during our stay."
MARISSA 2-night trip
Posted 6 hours ago
Microtel Inn & Suites by Wyndham Michigan City
Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"I did not like to see so many cannabis stores within walking distance of our hotel.."
Ricky 2-night trip
Posted 20 hours ago
Holiday Inn Express & Suites New Buffalo by IHG
Fairfield Inn and Suites By Marriott Merrillville

Fairfield Inn and Suites By Marriott Merrillville

8/10 Good
"The room was clean."
Georgene 1-night trip
Posted 1 day ago
Fairfield Inn and Suites By Marriott Merrillville
Comfort Inn Hammond I-94

Comfort Inn Hammond I-94

10/10 Excellent
"Nice"
David 5-night trip
Posted 1 day ago
Comfort Inn Hammond I-94
Baymont by Wyndham New Buffalo

Baymont by Wyndham New Buffalo

10/10 Excellent
"Hair dryer was broke and AC water was leaking from the room upper room. The staff changed my room. It was ok."
Fernanda 1-night trip
Posted 2 days ago
Baymont by Wyndham New Buffalo
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

10/10 Excellent
"Perfect"
Jeannette 2-night trip
Posted 3 days ago
Hilton Garden Inn Chesterton
Waterbird Lakeside Inn

Waterbird Lakeside Inn

10/10 Excellent
"Amazing stay. The balcony view was amazing. The room was huge. I highly recommend!"
Michelle 3-night trip
Posted 3 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. 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 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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