The Best Hotels with a Pool in Cleveland, WI from ￥14,221 in 2026

Q: What are some accommodations with pools in Cleveland?

Shoreline Serenity - 2 Private Acres : Vacation home, 1-minute walk from Lake Michigan. Features complimentary wireless internet access, a pool, and kitchens. Hidden Haven - Luxury Cottage w/ Hot Tub & Scenic Views : Hotel located near Lake Michigan. Features a private beach, an indoor pool, and cooked-to-order. Insane luxury beachfront estate - complete with indoor pool, arcade and theater! : Aparthotel, 14-minute walk from Lake Michigan. Offers daily, an indoor pool, and free self parking. Driftwood Cottage | Lake Michigan Sauna + Fire Pit : Hotel located near Lake Michigan. Features daily, an indoor pool, and free self parking. Lighthouse Inn : Resort located near Road America. Offers a seasonal outdoor pool, an indoor pool, and a full-service spa.

A rocky shoreline with waves crashing against the rocks and a large weeping willow tree in the background.

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Our top choices for Cleveland hotels with a pool

Indoor pool, open 6:00 AM to 10:00 PM, sun loungers

The Oasis Hotel & Bar

Sheboygan Falls

Splash into serenity at this Lake Michigan hotel with year-round indoor pool and arcade fun.

￥14,221 total

includes taxes & fees

Jul 2 - Jul 3

Lighthouse Inn

Two Rivers

Lakeside relaxation awaits with a private beach and stunning indoor pool, just steps from white sand shores of Lake Michigan.

￥18,835 total

includes taxes & fees

Jun 29 - Jun 30

Cobblestone Hotel & Suites - Two Rivers

Two Rivers

Luxurious indoor pool retreat beckons with year-round swimming and riverside relaxation in a clean, modern hotel setting.

￥16,214 total

includes taxes & fees

Jun 29 - Jun 30

Quality Inn Sheboygan North I-43

Sheboygan

Pool paradise awaits at this inviting hotel, where year-round swimming meets pure relaxation.

￥16,357 total

includes taxes & fees

Jul 8 - Jul 9

Wingate by Wyndham Sheboygan

Downtown Sheboygan

Dive into lakeside adventures with an indoor pool, arcade, and hiking trails nearby.

￥18,357 total

includes taxes & fees

Jul 5 - Jul 6

AmericInn by Wyndham Sheboygan

Sheboygan

Splash into warmth and comfort at this hotel's indoor pool oasis with year-round swim escapes.

￥18,569 total

includes taxes & fees

Jul 8 - Jul 9

Best Western Stanton Inn

Chilton

Relaxing indoor pool and hot tub experience awaits at this hotel with fitness amenities.

￥19,109 total

includes taxes & fees

Jun 30 - Jul 1

Holiday Inn Manitowoc by IHG

Manitowoc

Indoor oasis awaits with divine hot tub and pool for year-round swimming and relaxation.

￥17,808 total

includes taxes & fees

Jul 5 - Jul 6

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Choose what matters most at hotels with a pool in Cleveland

Breakfast included

4 stars

Top Cleveland Hotel Reviews

Lighthouse Inn

10/10 Excellent

"We enjoyed our stay there. We used the pool and hot tub and also had a wonderful breakfast. We were able to upgrade the breakfast for a small charge. The waitress was very helpful in giving us ideas as to where to visit while we were there. Very nice all around."

La Quinta Inn by Wyndham Sheboygan

10/10 Excellent

"We stayed here for Road America. Perfect location between the track and the great restaurants on the river near the lake in Sheboygan. Staff was amazing…special shout out to Brittany who was taking great care of everyone and keeping the common areas spotless during our stay!"

The Inn on Maritime Bay, an Ascend Collection Hotel

10/10 Excellent

"The location was wonderful, within walking distance to museums, shopping, parks, and spa. The view of the lake from the hotel was spectacular, especially when the ferry was docking. Access to the YMCA next door is another perk.Pool and sauna very nice too. A well managed hotel in a charming town."

Grandstay Residential Suites Hotel - Sheboygan

10/10 Excellent

"This is an excellent newer hotel in the older section of Sheboygan. It's in a quiet area of the downtown within walking distance of several good eating spots. The spacious lobby includes tables for the provided breakfast. Rooms were clean and comfortable. I would revisit this hotel on my next visit to Sheboygan."

Frequently asked questions

What are some accommodations with pools in Cleveland?

Shoreline Serenity - 2 Private Acres: Vacation home, 1-minute walk from Lake Michigan. Features complimentary wireless internet access, a pool, and kitchens. Hidden Haven - Luxury Cottage w/ Hot Tub & Scenic Views: Hotel located near Lake Michigan. Features a private beach, an indoor pool, and cooked-to-order. Insane luxury beachfront estate - complete with indoor pool, arcade and theater!: Aparthotel, 14-minute walk from Lake Michigan. Offers daily, an indoor pool, and free self parking. Driftwood Cottage | Lake Michigan Sauna + Fire Pit: Hotel located near Lake Michigan. Features daily, an indoor pool, and free self parking. Lighthouse Inn: Resort located near Road America. Offers a seasonal outdoor pool, an indoor pool, and a full-service spa.

What is there to see and do in Cleveland?

Explore places like Lake Michigan while you're in Cleveland. Take in the natural beauty with a stop at Fischer Creek State Recreation Area.

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

Taking into account the local weather in Cleveland is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Cleveland are January, March, February, and October, with each month seeing an average of 7 inches of snowfall.

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