Photo by Ruslian

Hotels with Swimming Pools in Chesterton

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chesterton Hotels with Swimming Pools

Tonight
27 Nov - 28 Nov
Tomorrow
28 Nov - 29 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Hotels with Swimming Pools in Chesterton

Indoor pool
Spring House Inn

Spring House Inn

2.5 star property
Chesterton
  • Indoor pool
  • Near the beach
8.8 out of 10, Excellent, (1013)
Gliding through crystal-clear waters, guests enjoy the indoor pool's year-round comfort after hiking nearby dunes trails. This hotel pairs aquatic relaxation with sauna sessions, creating a rejuvenating sanctuary amid picturesque woodland surroundings.
The price is S$136
includes taxes & fees
30 Nov - 1 Dec
Spring House Inn
Indoor pool
Best Western Indian Oak

Best Western Indian Oak

2.5 star property
Chesterton
  • Indoor pool
  • Near the beach
8.6 out of 10, Excellent, (1014)
Sauna sessions complement invigorating swims in the spacious indoor pool at this lakeside haven. Nature enthusiasts appreciate the proximity to hiking trails and Indiana Dunes National Park after refreshing dips in crystal waters.
The price is S$136
includes taxes & fees
8 Dec - 9 Dec
Best Western Indian Oak
Indoor pool
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3.0 star property
Chesterton
  • Indoor pool
8.8 out of 10, Excellent, (1001)
Swimming enthusiasts rejoice at the tranquil indoor pool, perfectly complemented by the 24-hour fitness centre for complete wellness during any season. After an invigorating workout, guests can unwind with drinks at the SouthShore Drift Co. restaurant and bar.
The price is S$150
includes taxes & fees
23 Dec - 24 Dec
Hilton Garden Inn Chesterton
Indoor spa tub
Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

2.5 star property
Chesterton
  • Indoor pool
  • Hot tub
8.0 out of 10, Very good, (1008)
Swimming enthusiasts discover aquatic bliss at the pristine indoor pool, complemented by a rejuvenating hot tub experience. After exploring nearby Bailly Homestead, guests appreciate the complimentary continental breakfast and well-maintained fitness centre.
The price is S$130
includes taxes & fees
7 Dec - 8 Dec
Comfort Inn & Suites Porter near Indiana Dunes
Seasonal outdoor pool, pool umbrellas, pool loungers
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

3.5 star property
New Buffalo
  • Poolside bar
  • Pool loungers
  • Near the beach
  • 2 hot tubs
9.4 out of 10, Exceptional, (1628)
Surrounded by natural beauty and trees, this hotel's poolside paradise features 2 inviting hot tubs for ultimate relaxation. Guests rave about the fun atmosphere, clean facilities, and excellent poolside bar service during summer months.
The price is S$115
includes taxes & fees
30 Nov - 1 Dec
Four Winds Casino Resort – New Buffalo
Indoor pool
Hampton Inn Crown Point

Hampton Inn Crown Point

2.5 star property
Crown Point
  • Indoor pool
9.4 out of 10, Exceptional, (599)
Swimming enthusiasts appreciate the pristine indoor pool at this modern retreat, complemented by an impressive 24-hour fitness centre. After invigorating morning laps, guests savour the highly-rated breakfast buffet featuring real eggs and smoked Polish sausage.
The price is S$138
includes taxes & fees
6 Dec - 7 Dec
Hampton Inn Crown Point
Indoor pool, pool loungers
Quality Inn Near Interstate I94

Quality Inn Near Interstate I94

2.5 star property
New Buffalo
  • Indoor pool
  • Pool loungers
  • Hot tub
8.4 out of 10, Very good, (1043)
Crystal-clear waters of the indoor pool welcome swimmers year-round, complemented by a bubbling hot tub for post-exploration relaxation. Surrounding sun loungers invite leisurely afternoons, while Lake Michigan adventures await just beyond this serene forest hideaway.
The price is S$93
includes taxes & fees
3 Dec - 4 Dec
Quality Inn Near Interstate I94
Indoor pool
Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

2.5 star property
New Buffalo
  • Indoor pool
8.8 out of 10, Excellent, (1005)
Crystal-clear waters await in the meticulously maintained indoor swimming pool, open until midnight for evening dips. After swimming, guests can unwind in the spotless hot tub before enjoying the complimentary breakfast buffet each morning.
The price is S$131
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express & Suites New Buffalo by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Black Friday Sale

Save up to 50% on select hotels
Book now

Top Chesterton Hotel Reviews

Country Inn & Suites by Radisson, Merrillville, IN

Country Inn & Suites by Radisson, Merrillville, IN

10/10 Excellent
"The people were nice and the place was very clean "
Howard 3-night trip
Posted 3 days ago
Country Inn & Suites by Radisson, Merrillville, IN

Explore a world of travel with Expedia

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. Comfort Inn & Suites Porter near Indiana Dunes: Offers daily, an indoor pool and free self parking. Best Western Indian Oak: Hotel located near Indiana Dunes National Park. Provides a sauna, an indoor pool and free self parking. Waterbird Lakeside Inn: Offers a snack bar/deli, an indoor pool and free self parking. Hilton Garden Inn Chesterton: Hotel steps from Four Winds Casino New Buffalo. Features 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.