The Best Hotels with a Pool in Highland, IN from ₩130,019 in 2026

Q: What are some accommodations with pools in Highland?

DoubleTree by Hilton Chicago - Alsip : Features free self parking, an indoor pool, and complimentary wireless internet access. Wind Creek Southland Casino and Hotel : Offers a snack bar/deli, an indoor pool, and complimentary wired internet access. EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG : Offers daily, an indoor pool, and free self parking. Motel 6 - Chicago, IL : Features a snack bar/deli, a pool, and buffet. Baymont by Wyndham Chicago/Alsip : Features a snack bar/deli, a seasonal outdoor pool, and daily.

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Our top choices for Highland hotels with a pool

Hyatt Place Munster

Munster

Escape to the indoor oasis at this art deco hotel, where poolside relaxation meets modern comfort.

₩277,564 total

includes taxes & fees

Jul 19 - Jul 20

Spring House Inn

Chesterton

Relax in the heated indoor pool surrounded by forest views at this tranquil retreat.

₩230,594 total

includes taxes & fees

Jun 28 - Jun 29

Holiday Inn Express & Suites Chicago Matteson by IHG

Matteson

Refresh yourself with a dip in the indoor pool after a workout in the fitness center at this modern hotel just outside Chicago.

₩199,297 total

includes taxes & fees

Jun 30 - Jul 1

Hampton Inn Crown Point

Crown Point

Indoor pool sanctuary with 24-hour fitness center offers year-round aquatic bliss.

₩251,666 total

includes taxes & fees

Jul 2 - Jul 3

Hampton Inn Portage

Portage

Dive into relaxation at this inviting Portage pool oasis just steps from Indiana Dunes National Park.

₩202,701 total

includes taxes & fees

Jul 26 - Jul 27

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.

₩163,540 total

includes taxes & fees

Jul 13 - Jul 14

Sleep Inn & Suites Merrillville

Merrillville

Merrillville hotel offers poolside tranquility with sun-drenched relaxation and convenient amenities.

₩153,062 total

includes taxes & fees

Jul 2 - Jul 3

Comfort Inn Hebron-Lowell Area

Hebron

Escape the summer heat with a dip in the hotel's seasonal outdoor pool in the heart of the city.

₩208,610 total

includes taxes & fees

Jul 26 - Jul 27

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Choose what matters most at hotels with a pool in Highland

Breakfast included

Hot tub

Top Highland Hotel Reviews

Country Inn & Suites by Radisson, Merrillville, IN

8/10 Good

"The staff were very helpful and friendly. There was enough parking in the parking lot. The breakfast was good. The room was clean but, the room smelled like black and milds. The bathroom ceiling was pilling over the shower. But other than that. Our stay was great."

Days Inn and Suites by Wyndham Hammond, IN

8/10 Good

"The revolving front door and two of the elevators weren’t operable. The ice machine on our floor was not working either. This made coming and going more challenging than necessary. The room was excellent. It was clean, spacious and very comfortable. The morning breakfast was inconsistent. The first morning, part of the buffet was difficult to access because the foldable walls were extended early. There was also a scramble when they started to shut down the breakfast a few minutes early. The food itself was good and plentiful. The manager’s reception was nice. The bartenders were friendly and efficient. The snacks were limited but didn’t run out. The overall experience was good. These few access points and amenities being addressed would have made it great. A last point, I wish the hotel would have been more forthcoming about the parking charge. I don’t mind paying for parking but was surprised to be chador a self parking surface lot."

Frequently asked questions

What are some accommodations with pools in Highland?

DoubleTree by Hilton Chicago - Alsip: Features free self parking, an indoor pool, and complimentary wireless internet access. Wind Creek Southland Casino and Hotel: Offers a snack bar/deli, an indoor pool, and complimentary wired internet access. EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG: Offers daily, an indoor pool, and free self parking. Motel 6 - Chicago, IL: Features a snack bar/deli, a pool, and buffet. Baymont by Wyndham Chicago/Alsip: Features a snack bar/deli, a seasonal outdoor pool, and daily.

What is there to see and do in Highland?

Explore places like Indiana Dunes National Park while you're in Highland. Surround yourself with nature at Hoosier Prairie.

When is the best time to book a hotel with a pool in Highland?

You may want to think about an accommodation with an outdoor swimming pool if you plan to visit Highland in the hottest months of July, August, or June when the average temp is 71°F. Lodging offering an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temperature is 31°F.

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