Book Hotels in Cleveland, WI
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Top Cleveland hotels

Shoreline Serenity - 2 Private Acres
Cleveland WI
This cottage features a garden, laundry facilities, and barbecue grills.
"The place was absolutely gorgeous, clean, warm, beautifully decorated. The weather was a bit unpredictable but the storms were nice to watch from the living room wall of windows by the fireplace. The waves crashing against shore was a calming lullaby. The kitchen was sufficiently stocked with necessities ..."
Reviewed on May 13, 2026

Insane luxury beachfront estate - complete with indoor pool, arcade and theater!
Cleveland WI
This vacation home features an indoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on ...
"Awesome!"
Reviewed on May 23, 2026

Hidden Haven - Luxury Cottage w/ Hot Tub & Scenic Views
Cleveland WI
A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
"Awesome place! Second time I’ve stayed and plan on going back!"
Reviewed on May 19, 2026

Watershed Hotel
838 N 15th St Sheboygan WI
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $189 total per night from Jun 25 to Jun 26
$189 total
Jun 25 - Jun 26
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of ...
"One of the best and cleanest hotels i have ever stayed at. If/when I return to Wisconsin, I will 10000% be booking at this hotel again. The staff and people at the front desk couldn't have been nicer. A 10 out of 10 stay for me. I stayed on the river side and being able to open up the door every ..."
Reviewed on Jun 4, 2026

The Osthoff Resort
101 Osthoff Avenue Elkhart Lake WI
$282 nightly
The price is $317 total per night from Jun 6 to Jun 7
$317 total
Jun 6 - Jun 7
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center ...
"Everything was great."
Reviewed on Jun 1, 2026

Grandstay Residential Suites Hotel - Sheboygan
708 Niagara Avenue Sheboygan WI
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $211 total per night from Jun 10 to Jun 11
$211 total
Jun 10 - Jun 11
Total with taxes and fees
This aparthotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...
"Room was spacious and clean. Central location close to restaurants and the beach. All walkable and felt safe walking around. Property was very dated, workout room was tight and cramped with 3 cardio machines in there. Small indoor pool, good for kids. When I arrived around 8-9pm, there was no one ..."
Reviewed on Jun 3, 2026

Driftwood Cottage | Lake Michigan Sauna + Fire Pit
Cleveland WI
A sauna is featured at this vacation home, along with a garden and barbecue grills.

Lighthouse Inn
1515 Memorial Dr Two Rivers WI
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $137 total per night from Jun 7 to Jun 8
$137 total
Jun 7 - Jun 8
Total with taxes and fees
A private beach and a restaurant are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport ...

The American Club
419 Highland Drive Kohler WI
Fully refundableReserve now, pay when you stay
$568 nightly
The price is $627 total per night from Jul 1 to Jul 2
$627 total
Jul 1 - Jul 2
Total with taxes and fees
A full-service spa, 3 restaurants, and 4 indoor tennis courts are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour ...
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.
Frequently asked questions
Recent Cleveland hotel reviews by fellow wanderers

Watershed Hotel
5 out of 5
Posted 1 day ago
Travelocity Verified Review
"One of the best and cleanest hotels i have ever stayed at. If/when I return to Wisconsin, I will 10000% be booking at this hotel again. The staff and people at the front desk couldn't have been nicer. A 10 out of 10 stay for me. I stayed on the river side and being able to open up the door every morning to the Sheboygan River was the cherry on top. Fantastic hotel"
A verified traveler stayed at Watershed Hotel
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