Cleveland Holiday Rentals, Wisconsin: Private House Rentals

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

An indoor swimming pool with wooden walls and ceiling, surrounded by white lounge chairs and tables.

A pathway leading to a building with a patio area, surrounded by sunflowers and marigolds.

A hotel room with a bed, a sofa, a desk, and a painting on the wall.

A hotel room with a bed, a sofa, a desk, and a television.

1. Quality Inn Sheboygan North I-43

Sheboygan

Christine

฿2,679

฿3,041 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor patio area with tables and chairs, string lights, and a view of the building in the background.

A buffet counter with a coffee machine, a display case with food, and a digital menu board.

An indoor swimming pool with a geometric ceiling design, a seating area with chairs, and a view of the outdoors through large windows.

A multi-story hotel with a modern design, featuring a covered outdoor seating area and a visible fire feature.

2. Home2 Suites By Hilton Sheboygan

Sheboygan

Scott

฿4,817

฿5,467 total

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with a marble countertop, a coffee machine, and various food items displayed.

A spacious lobby with a wooden staircase, a reception desk, and a seating area.

A modern living room with a sofa, armchairs, and a coffee table.

A modern hotel bathroom with a large mirror, a sink, and a shower area.

3. La Quinta Inn by Wyndham Sheboygan

Sheboygan

Tony Michael Williams

฿3,069

฿3,483 total

includes taxes & fees

1 Nov - 2 Nov

A modern interior with a stone fireplace, seating area, and a flat-screen TV mounted above it.

A modern building entrance with glass doors, a covered walkway, and a view of a green landscape.

A modern hotel with a flat roof, large windows, and a sign reading "The Watershed."

A modern interior with a stone fireplace, large windows, and a flat-screen TV above it.

4. Watershed Hotel

Sheboygan

Stephan

฿4,376

฿4,966 total

includes taxes & fees

13 Oct - 14 Oct

An indoor swimming pool with wooden walls and ceiling, surrounded by tables and chairs.

A hotel room with a bed, a red chair, a wooden door, a nightstand with a lamp, and a bathtub.

A restaurant interior with a bar area, multiple seating options including bar stools and tables, and wall decorations.

A hotel with a covered entrance, brick pillars, and a sign indicating it is an American hotel.

5. AmericInn by Wyndham Manitowoc

Manitowoc

Kimberly

฿3,392

฿3,849 total

includes taxes & fees

19 Oct - 20 Oct

A spacious living area with a fireplace, a sofa, and a dining area in the background.

A swimming pool with a no diving sign, chairs around it, and a max pool capacity sign.

A hotel room with two beds, a sofa, a TV, and a dining table.

A GrandStay hotel with a modern design, featuring a prominent entrance and a clear view of the parking area.

6. Grandstay Residential Suites Hotel - Sheboygan

Downtown Sheboygan

Kristin

฿4,024

฿4,567 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with two beds, a desk, and a window with a view of a parking lot.

A Super 8 motel with a red roof, brick facade, and a signboard.

A laundry room with two washing machines, a storage door, and a control panel.

A bathroom with a sink, mirror, towel rack, and toiletries.

7. Super 8 by Wyndham Sheboygan WI

Sheboygan

David

฿2,535

฿2,877 total

includes taxes & fees

11 Nov - 12 Nov

A spacious dining area with white chairs and tables, large windows with blinds, and a view of the outdoors.

A modern living room with a grey sofa, a coffee table, and a dining area with a wooden table and chairs. A kitchen with white cabinets and stainless steel appliances is visible in the background.

An outdoor patio with seating, a fire pit, and umbrellas.

A modern interior with a stone wall, a flat-screen TV, a fireplace, a sofa, and a staircase.

8. Harbor Town, BW Signature Collection

Manitowoc

Patrick

฿2,463

฿2,796 total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with clear blue water, tiled walls, and large windows offering a view of a field.

A reception area with two counters, a marble wall, an ATM, and a staircase.

A spacious lobby with marble flooring, vending machines, and a staircase.

A neatly made bed with white bedding, two bedside lamps, a dark headboard, and a small bedside table with a phone and a lamp.

9. The Oasis Hotel & Bar

Sheboygan Falls

Gregory

฿2,686

฿2,968 total

includes taxes & fees

13 Oct - 14 Oct

A Holiday Inn Express hotel with a brick facade, a covered entrance, and an American flag.

A modern dining area with a central island, bar stools, and a sofa.

An indoor swimming pool with clear blue water, surrounded by white chairs and tables, and large windows offering views of the outdoors.

A hotel room with a sofa, a desk, a chair, a television, and a window with curtains.

10. Holiday Inn Express Sheboygan-Kohler by IHG

Sheboygan

฿4,091

฿4,643 total

includes taxes & fees

16 Oct - 17 Oct

An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled deck.

A breakfast area with wooden tables and chairs, a coffee station, and a wall-mounted TV.

A hotel room with two beds, a desk with a computer, a TV, and a window with curtains.

A hotel room with a flat-screen TV, a desk with a chair, a bed, a sofa, and a large window with curtains.

11. Baymont by Wyndham Plymouth

Plymouth

Paula

฿4,195

฿4,761 total

includes taxes & fees

13 Oct - 14 Oct

A modern hotel entrance with a curved canopy, multiple floors, and a prominent sign.

A swimming pool with a lifeguard sign, lounge chairs, and a view of the outdoors.

A modern restaurant with wooden accents, white tiled walls, and yellow chairs.

A reception area with a wooden reception desk, a digital display, and a refrigerator stocked with beverages.

12. Fairfield Inn & Suites by Marriott Sheboygan

Sheboygan

Lawrence

฿3,962

฿4,496 total

includes taxes & fees

30 Oct - 31 Oct

A hotel lobby with a glass door leading to a pool area.

A hotel room with a sofa, armchair, and a small table. There is a mirror on the wall and a lamp. The room has a carpeted floor and a picture of a sunset on the wall.

A living room with two couches, a coffee table, and a round mirror on the wall.

13. Holiday Inn Manitowoc by IHG

Manitowoc

Patricia

฿3,118

฿3,539 total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with lounge chairs and tables, a clear blue pool, and a high ceiling with visible structural beams.

A hotel room with two beds, a desk, a chair, a TV, and an air conditioning unit.

A conference room with a long table, six chairs, and a wooden accent wall.

A reception area with a wooden reception desk, a flat-screen TV, and a seating area with two chairs and a small table.

14. Wingate by Wyndham Sheboygan

Downtown Sheboygan

Joell

฿2,626

฿2,981 total

includes taxes & fees

18 Oct - 19 Oct

A spacious living area with a stone fireplace, comfortable seating, and a balcony with a railing.

A family sitting by a poolside with chairs and a tiled wall in the background.

A coffee station with a chalkboard sign reading "Welcome to the Beginning of Day!" and various coffee-making equipment.

A hotel room with a bed, a desk with a sink, a chair, a small table, and a window with curtains.

15. AmericInn by Wyndham Sheboygan

Sheboygan

Diane

฿2,879

฿3,267 total

includes taxes & fees

1 Nov - 2 Nov

A kitchen with dark cabinets, a wooden countertop, and pendant lights.

A waterfront hotel with a prominent sign, a flagpole, and a reflection in the water.

A hotel room with two beds, a desk, a chair, a TV, and framed pictures on the walls.

A restaurant with multiple tables and chairs, large windows, and a view of the outside.

16. Harbor Winds Hotel

Sheboygan

Theresa

฿3,279

฿3,721 total

includes taxes & fees

9 Nov - 10 Nov

A restaurant with a clean, modern interior featuring a central dining area with tables and chairs, a kitchen area with appliances and a refrigerator, and wall decorations including fruit and waffle images.

A hotel room with two beds, a nightstand with a lamp, and a headboard.

A gym with a treadmill, weight bench, and various exercise machines.

A room with two sofas, a small round table with a vase, and a large abstract painting on the wall.

17. Quality Inn Manitowoc

Manitowoc

Anna

฿2,423

฿2,783 total

includes taxes & fees

9 Nov - 10 Nov

A spacious atrium with a grand chandelier, multiple balconies, and large windows allowing natural light.

A beachfront hotel with multiple red-roofed buildings, a sandy path leading to the beach, and clear blue water.

A large, white building with a symmetrical facade and multiple balconies.

A coastal hotel with a wooden boardwalk leading to beach chairs.

18. Blue Harbor Resort and Conference Center

Sheboygan

Alexis

฿6,169

฿7,886 total

includes taxes & fees

13 Oct - 14 Oct

A hotel with a curved facade, illuminated signage, and snow-covered surroundings.

A cozy living room with a fireplace, leather furniture, and a chandelier.

A spa area with a green heated floor, a ceiling with a cloud mural, and two relaxation chairs on either side.

Two people sitting on a couch facing a fireplace with a fruit platter on the table.

19. Inn On Woodlake

Kohler

MARTHA

฿7,678

฿8,485 total

includes taxes & fees

1 Nov - 2 Nov

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Stay near popular Cleveland attractions

Fischer Creek State Recreation Area

You can take time to visit Fischer Creek State Recreation Area during your travels to Cleveland.

See properties

Dairyland Park

Dairyland Park is just one of the places to see in Cleveland, so why not enjoy the other things to explore during your travels?

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Veterans Memorial Park

Explore the great outdoors at Veterans Memorial Park, a lovely green space in Cleveland.

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Learn more about Cleveland

Nestled along Lake Michigan's shores, this charming village invites visitors to hike scenic trails at Fischer Creek State Recreation Area. Spend sunny afternoons at North Side Municipal Beach before exploring Hika Bay and the peaceful grounds of Veterans Memorial Park.

See all hotels in Cleveland

Top Cleveland Hotel Reviews

Watershed Hotel

10/10 Excellent

"We enjoyed the great view from our balcony of the river. The walk-in shower and plentiful counter space in the bathroom (the night light was a good bonus!) were very nice. Front desk was so very helpful with ideas for our stay. A wonderful modern hotel and reasonably priced."

Blue Harbor Resort and Conference Center

10/10 Excellent

"Wonderful hotel, so much to do, clean and comfortable"

Village Inn on the Lake

10/10 Excellent

"Was a very quiet, restful experience. It was a home Packer game (Bears) and with the RV park, I expected a bit more activity. The room was very equipped, full size fridge/freezer, range, sink & microwave. Basic kitchen essentials, large room & bathroom. Couch wasn't the most comfortable to sit on, but that's expected in a hotel. We brought our bikes & they stored them in a locked shed for us. Super helpful."

AmericInn by Wyndham Sheboygan

8/10 Good

"no complaints. would visit again."

Grandstay Residential Suites Hotel - Sheboygan

8/10 Good

"Very friendly staff. The property was clean except people smoking right by the entrance. Maybe move the receptical further away and dont allow smoking past the parking lot. Breakfast was ok. Suggest a bigger toaster or have 2. Coffee was always empty. Apple juice was watery. Our room had a bad oder. The fan didn't work in the bathroom. The beds were extremely hard and not comfortable. The couch seats were low compared to the armrests and were uncomfortable because it had a bed inside and the bars dug into your legs. The room layout was very nice. 2 separate bedrooms instead of 2 beds next to each other and they were separated by the living room. The price was fair for the room we booked. The pool is very small and not very deep. There was no hot tub, that was a bummer."

Cobblestone Hotel & Suites - Two Rivers

10/10 Excellent

"Very nice"

The Oasis Hotel & Bar

8/10 Good

"Nice spacious room, comfortable bed. Helpful staff as always."

La Quinta Inn by Wyndham Sheboygan

8/10 Good

"Room was clean. Smelled like the perfume strippers wear. Staff was friendly and helpful. Sign said rooms not made up on Friday and Sunday unless requested. We stayed over and our room was not made up on Saturday, but trash removed. VERY convenient to Road America. Don’t know if restaurants are near, but there is a McDonald’s very close. Would stay here again."

Fairway Inn and Suites, an Ascend Collection Hotel

8/10 Good

"f"

More cheap stays in Cleveland

Harbor Town, BW Signature Collection

4004 Calumet Ave. Manitowoc WI

฿2,463

฿2,796 total

1 Nov - 2 Nov

includes taxes & fees

The Oasis Hotel & Bar

600 N Main St Sheboygan Falls WI

฿2,686

฿2,968 total

13 Oct - 14 Oct

includes taxes & fees

8/10 Very good! (440 reviews)

Quality Inn Sheboygan North I-43

4332 N 40th St Sheboygan WI

฿2,679

฿3,041 total

1 Nov - 2 Nov

includes taxes & fees

Comfort Inn & Suites Sheboygan I-43

3912 Motel Rd Sheboygan WI

฿2,690

฿3,054 total

9 Nov - 10 Nov

includes taxes & fees

Lighthouse Inn

1515 Memorial Dr Two Rivers WI

฿3,521

฿3,996 total

1 Nov - 2 Nov

includes taxes & fees

9/10 Wonderful! (1,013 reviews)

Grandstay Residential Suites Hotel - Sheboygan

708 Niagara Avenue Sheboygan WI

฿4,024

฿4,567 total

1 Nov - 2 Nov

includes taxes & fees

8.6/10 Excellent! (1,106 reviews)

Frequently asked questions

What's the best place to stay in Cleveland?

Located 0.7 mi (1.1 km) from the heart of Cleveland, Lighthouse Inn is a top choice for your stay, based on our traveller data. Other good choices for your trip to the area are Grandstay Residential Suites Hotel - Sheboygan and Watershed Hotel. See all available top hotels, or vacation rentals in Cleveland.

If I need to cancel my hotel reservation in Cleveland, will I receive a refund?

Yes, the majority of hotel bookings are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If you booked a non-refundable reservation, you might be able to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Cleveland.

What are some accommodation options with pools in Cleveland?

Lighthouse Inn: Hotel, 1-minute walk from Lake Michigan. Offers a private beach, an indoor pool and cooked-to-order. Grandstay Residential Suites Hotel - Sheboygan and Cobblestone Hotel & Suites - Two Rivers are a couple of other choices with an on-site pool. View all hotels with pools in Cleveland.

What's it like staying in Cleveland?

Those travelling to Cleveland will definitely enjoy the sights to see and things to do. A top sight in the city is Lake Michigan. In Cleveland, there are 14 hotels and other accommodation options to choose from. Find out more about Cleveland.

What should I do while I'm visiting Cleveland?

Favourite places to visit include Lake Michigan, Veterans Memorial Park and Hika Bay. Additionally, you might want to add Fischer Creek State Recreation Area to your itinerary. Take a look at what more there is to see and do in Expedia's Cleveland guide.

What's the seasonal weather like in Cleveland?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cleveland are January, March, February and October, with each month seeing an average of 17 cm of snowfall.

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Book Hotels in Cleveland on Expedia.com

Find hotels in Cleveland, WI from ฿2,783

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Cleveland

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Cleveland hotels

1. Quality Inn Sheboygan North I-43

2. Home2 Suites By Hilton Sheboygan

3. La Quinta Inn by Wyndham Sheboygan

4. Watershed Hotel

5. AmericInn by Wyndham Manitowoc

6. Grandstay Residential Suites Hotel - Sheboygan

7. Super 8 by Wyndham Sheboygan WI

8. Harbor Town, BW Signature Collection

9. The Oasis Hotel & Bar

10. Holiday Inn Express Sheboygan-Kohler by IHG

11. Baymont by Wyndham Plymouth

12. Fairfield Inn & Suites by Marriott Sheboygan

13. Holiday Inn Manitowoc by IHG

14. Wingate by Wyndham Sheboygan

15. AmericInn by Wyndham Sheboygan

16. Harbor Winds Hotel

17. Quality Inn Manitowoc

18. Blue Harbor Resort and Conference Center

19. Inn On Woodlake

Stay near popular Cleveland attractions

Fischer Creek State Recreation Area

Dairyland Park

Veterans Memorial Park

Learn more about Cleveland

Top Cleveland Hotel Reviews

Watershed Hotel

Blue Harbor Resort and Conference Center

Village Inn on the Lake

AmericInn by Wyndham Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

Cobblestone Hotel & Suites - Two Rivers

The Oasis Hotel & Bar

La Quinta Inn by Wyndham Sheboygan

Fairway Inn and Suites, an Ascend Collection Hotel

More cheap stays in Cleveland

Harbor Town, BW Signature Collection

The Oasis Hotel & Bar

Quality Inn Sheboygan North I-43

Comfort Inn & Suites Sheboygan I-43

Lighthouse Inn

Grandstay Residential Suites Hotel - Sheboygan

Frequently asked questions

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