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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 holiday homes

A spacious living room with a sofa, armchairs, a coffee table, and a TV mounted on the wall. There is a dining area in the background with a table and chairs.

A sign for General King City of Sheboygan with a flag and a view of the water in the background.

A coffee bar setup with a Hamilton Beach Flexbrew coffee maker, sugar dispenser, and various coffee pods.

A hotel room with a bed, a chair, a bedside table with lamps, a mirror, and a window with curtains.

1. 3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

Sheboygan

9.8 out of 10, Exceptional, (19 reviews)

9.8/10

Exceptional

(19 reviews)

"Great place to stay and only a short walk to the beautiful beach."

Brian L.

The price is £140

£140

includes taxes & fees

8 Oct - 9 Oct

3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

A modern living room with a staircase, a blue sofa, a wooden coffee table, and a cityscape painting.

A modern living room with a large TV, wooden entertainment unit, and a cozy seating area.

A modern kitchen with a stainless steel sink, a window with a view of trees, and a framed picture on the wall.

2. The Links! - Luxury Golf Retreat with Golf Simulator

The Links! - Luxury Golf Retreat with Golf Simulator

Sheboygan

10.0 out of 10, Exceptional, (14 reviews)

10/10

Exceptional

(14 reviews)

"Home was very clean and had everything we needed. Beds were comfortable. Easy to find and close to everything. "

Andrea S.

The price is £453

£453

includes taxes & fees

1 Nov - 2 Nov

The Links! - Luxury Golf Retreat with Golf Simulator

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

A spacious dining area with a wooden table and chairs, a chandelier, and a view into the living room.

A golf course with bunkers and a view of the ocean.

A modern kitchen with a wooden table and chairs, a hanging light fixture, and a bench in the corner.

3. The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

Sheboygan

10.0 out of 10, Exceptional, (42 reviews)

10/10

Exceptional

(42 reviews)

"Many extras that we have never seen at other rentals.Children's toys, beach toys, dog extras- leash dog bowls towels and a new toy to bring home. Walking distance to Lake Michigan. Restaurants that are 5 min distance driving. Kohler Andrae 15 min away! Kitchen had every item you would need.Hope to say again. Thanks for a great experience"

Anonymous traveller

The price is £298

£298

includes taxes & fees

2 Nov - 3 Nov

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

A dining table with a vase of green leaves and a candle.

A living room with two armchairs, a small round table, a patterned rug, and a bookshelf with books.

A room with a brown leather sofa, a framed landscape painting, a floor lamp, and a woven wall hanging.

A bedroom with a bed, two bedside tables, a nightstand, a wall-mounted lamp, a framed landscape painting, and a vase with dried plants.

4. Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Sheboygan

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"The house was great! It had everything we needed, was very clean, and cozy. We enjoyed our stay and Ginger was welcoming, available, and responsive. "

Christine P.

The price is £179

£179

includes taxes & fees

1 Nov - 2 Nov

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

An outdoor seating area with a view of a lake, surrounded by trees and a barbecue grill.

A lakeside garden with a stone border, a dock, and a chair by the water.

A view through a window of a well-maintained lawn with a pond, trees, and a white fence.

A sandy beach with footprints, a clear sky, and a tree line in the distance.

5. New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

Two Rivers

10.0 out of 10, Exceptional, (48 reviews)

10/10

Exceptional

(48 reviews)

"So delightful and a wonderful stay!"

Tom & Jenny S.

The price is £182

£182

includes taxes & fees

19 Oct - 20 Oct

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

A neatly made bed with a wooden headboard, a nightstand with a lamp, and a large mirror.

A kitchen with white cabinets, a microwave, a toaster, and a coffee maker.

A living room with a sectional sofa, a coffee table, a lamp, and a wall-mounted picture.

A residential area with houses surrounded by trees, a clear sky, and a distant view of the horizon.

6. Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

Sheboygan

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Just like the description. Very clean. Accommodations for kids and the host was very accommodating!"

Erin S.

The price is £264

£264

includes taxes & fees

12 Oct - 13 Oct

Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

A living room with a sofa, coffee table, and TV.

A dining area with a wooden table and chairs, a kitchen in the background, and a children's arcade game.

A modern kitchen with white cabinets, a wooden floor, and a built-in oven.

A narrow hallway with a dark wooden staircase, white walls, and a white door at the end.

7. Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Sheboygan

9.8 out of 10, Exceptional, (42 reviews)

9.8/10

Exceptional

(42 reviews)

"Great value. Cheaper and better than any hotel. "

Nicholas R.

The price is £453

£453

includes taxes & fees

7 Oct - 8 Oct

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

A room with a wooden ceiling, large windows, and a seating area with two chairs and a table.

A modern kitchen with a stainless steel refrigerator, a microwave, and a wooden countertop.

A dining area with a wooden table, white chairs, and a vase with branches.

A bedroom with a large bed, bedside lamps, a mirror, and a painting on the wall.

8. 1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

Two Rivers

9.6 out of 10, Exceptional, (14 reviews)

9.6/10

Exceptional

(14 reviews)

"Great place to stay."

Melissa B.

The price is £416

£416

includes taxes & fees

7 Oct - 8 Oct

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

A cabin with a deck, a covered porch, and a paved driveway.

A dirt road flanked by tall trees in a forested area.

A house with a paved driveway, surrounded by a wooded area.

A bedroom with a bed, dresser, TV, and a door leading outside.

9. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude

Elkhart Lake

10.0 out of 10, Exceptional, (71 reviews)

10/10

Exceptional

(71 reviews)

"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"

Barbara

The price is £212

£212

includes taxes & fees

7 Oct - 8 Oct

The Esker Ridge Chalet, Pristine Elkhart Solitude

A modern kitchen with a central island, wooden cabinets, and a built-in stove. There is a dining area with a table and chairs, and a living room with a sofa and a fireplace.

A modern kitchen with a stainless steel sink, white cabinetry, and a hanging pendant light.

A two-story house with a front porch, large windows, and a small garden.

A bedroom with a bed, a ceiling fan, a wardrobe, and a window.

10. Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

Sheboygan

10.0 out of 10, Exceptional, (17 reviews)

10/10

Exceptional

(17 reviews)

"Everything was clean and spacious. Had a great time and would definitely stay again! "

Brad T.

The price is £733

£733

includes taxes & fees

8 Oct - 9 Oct

Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

A spacious lobby with leather sofas, a chandelier, a large TV, and a foosball table.

A modern kitchen with white cabinets, a stainless steel stove, and a dishwasher.

A room with a large safe, a shower, and a vanity with a mirror.

A hallway with a tiled floor, framed certificates on the wall, and a view into a room with a piano and a chandelier.

11. Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

Kiel

8.8 out of 10, Excellent, (6 reviews)

8.8/10

Excellent

(6 reviews)

"This is an amazing and fun property. If you are in town for any event at Road America it makes it a little more special."

Ryan K.

The price is £383

£383

includes taxes & fees

17 Oct - 18 Oct

Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

A living room with a fireplace, a large clock, and a dining area with wooden furniture.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a granite countertop.

A house with a covered porch, a chimney, and a deck with chairs.

A living room with a sofa, armchairs, a coffee table, and a rug. There is a door with a wreath, a small table, and a window with curtains.

12. Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Oostburg

10.0 out of 10, Exceptional, (146 reviews)

10/10

Exceptional

(146 reviews)

"Super clean and a nice quiet place to stay!"

Elisabeth D.

The price is £134

£134

includes taxes & fees

7 Oct - 8 Oct

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

A patio with a fire pit, outdoor seating, and string lights.

A metallic elevator control panel with a horizontal handle and two vertical buttons, set against a wall with vertical tile patterns.

A modern kitchen with wooden cabinets, a black refrigerator, and a dining area with a wooden table and chairs.

A modern living room with a beige armchair, a round coffee table with a plant, a red sectional sofa, and a wooden floor.

13. 3 Min to Road America, "Amazing Location!!"

3 Min to Road America, "Amazing Location!!"

Plymouth

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Great place with tons of space and updated rooms. Conveniently located for everything we did. I would absolutely recommend this place!!"

Patrick F.

The price is £662

£662

includes taxes & fees

8 Oct - 9 Oct

3 Min to Road America, "Amazing Location!!"

A wooden deck with a bench, a door with frosted glass, and two wall-mounted lights.

A spacious living room with a large beige sectional sofa, two grey sofas, a wooden coffee table, and a ceiling fan.

A kitchen with wooden cabinets, a microwave, a stove, and a coffee maker.

A dining area with a wooden table and chairs, a kitchen with wooden cabinets, and a ceiling fan.

14. Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Reedsville

9.8 out of 10, Exceptional, (36 reviews)

9.8/10

Exceptional

(36 reviews)

"Our 4th time here. Great stay as always."

Jason R.

The price is £366

£366

includes taxes & fees

12 Oct - 13 Oct

Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

A wooden sign with "Woodland Cottage" written on it, surrounded by potted flowers and greenery.

A kitchen with wooden cabinets, a stove, a dishwasher, and a window with a view of trees.

A bedroom with a large bed, a bedside table, a wall clock, and two windows with blinds.

A spacious living room with a beige sofa, a white armchair, a small round table, and a television.

15. Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

New Holstein

10.0 out of 10, Exceptional, (181 reviews)

10/10

Exceptional

(181 reviews)

"We stay there every year and are never disappointed. Great location and experience. Thank you!"

Doug S.

The price is £254

£254

includes taxes & fees

12 Oct - 13 Oct

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

A spacious living area with a modern staircase, a fireplace, and a flat-screen TV mounted on the wall.

A geodesic dome house with a flat roof, a small entrance, and a balcony with a railing.

A dining area with a large table, chairs, a chandelier, and a view of trees through large windows.

A deck with outdoor furniture, a clear sky, and a grassy field.

16. Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

Plymouth

9.8 out of 10, Exceptional, (18 reviews)

9.8/10

Exceptional

(18 reviews)

"Everything was amazing and if we come back next year we will be staying again"

Cristy

The price is £440

£440

includes taxes & fees

27 Oct - 28 Oct

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

A bedroom with a bed, a window, a radiator, a framed picture on the wall, and a wooden headboard.

A two-story house with a stone facade and a blue exterior.

A park pathway lined with trees and a grassy area.

A grassy outdoor area with a wooden deck, a small shed, and a green hose coiled on the ground.

17. 5 min from Road America. Great yard and plenty of parking

5 min from Road America. Great yard and plenty of parking

Elkhart Lake

9.8 out of 10, Exceptional, (8 reviews)

9.8/10

Exceptional

(8 reviews)

" We enjoyed our stay very much. The house is lovely, spacious, and clean. The property is quite big and provides an excellent space to walk or room for younger children to play. Several family members enjoyed a walk about after our drive on Saturday. The house was perfect for our group, and the living room was our gathering place for Saturday evening as well as Sunday morning. We cooked our evening meal and our morning breakfast in the kitchen. The only minor issue was that our group had 9...

Paul & Jacqleene M.

The price is £832

£832

includes taxes & fees

9 Oct - 10 Oct

5 min from Road America. Great yard and plenty of parking

A deck with a hot tub, outdoor seating, and a view of a forested area.

A spacious kitchen with wooden cabinets, stainless steel appliances, and a large island with bar stools.

A spacious living room with a fireplace, a large sectional sofa, and a dining area.

A two-story house with a covered patio, a garage, and a driveway.

18. Stunning private home hidden in the woods. Can sleep 11 guests

Stunning private home hidden in the woods. Can sleep 11 guests

Plymouth

10.0 out of 10, Exceptional, (20 reviews)

10/10

Exceptional

(20 reviews)

"Our stay was great! Really enjoyed it!"

Nic B.

The price is £725

£725

includes taxes & fees

8 Oct - 9 Oct

Stunning private home hidden in the woods. Can sleep 11 guests

A dining area with a table, chairs, and a window with curtains.

A room with two beds, each with a white headboard and orange bedding. There are two wall-mounted lamps on either side of the beds.

A kitchen with a stainless steel refrigerator, a microwave on top, a coffee maker, and a small shelf with various items.

19. Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

Sheboygan

The price is £188

£188

includes taxes & fees

20 Oct - 21 Oct

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

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.

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Top Cleveland Hotel Reviews

Watershed Hotel

10/10 Excellent

"Very clean and comfortable hotel! Breakfast was ok but everything else was great"

Eric 1-night trip

Posted 4 hours ago

Watershed Hotel

Grandstay Residential Suites Hotel - Sheboygan

8/10 Good

"Location was disappointing. We were driving everywhere for sightseeing and restaurants."

Barbara 2-night trip

Posted 9 hours ago

Grandstay Residential Suites Hotel - Sheboygan

Quality Inn Sheboygan North I-43

8/10 Good

"The room was great. When going into hot tube it was hard to have a conversation with my partner cause kids where being so loud. The staff did nothing"

Sarah 1-night trip

Posted 9 hours ago

Quality Inn Sheboygan North I-43

Village Inn on the Lake

10/10 Excellent

"Nice stay."

Valerie 2-night trip

Posted 1 day ago

Village Inn on the Lake

Harbor Town, BW Signature Collection

10/10 Excellent

"Clean especially for an older hotel."

RYAN 1-night trip

Posted 2 days ago

Harbor Town, BW Signature Collection

The Osthoff Resort

8/10 Good

"Be sure to ask how to find your room. The staff handed me a omap, but didn’t mention you need to go through the main lobby, even after you check in, and it’s a very large resort."

Edward 2-night trip

Posted 2 days ago

The Osthoff Resort

Holiday Inn Manitowoc by IHG

10/10 Excellent

"Great stay! Quiet and very clean!!"

Patricia 1-night trip

Posted 7 days ago

Holiday Inn Manitowoc by IHG

Blue Harbor Resort and Conference Center

10/10 Excellent

"Perfect weekend getaway spent looking out the balcony at the beach waves!"

Alexis 1-night trip

Posted 9 days ago

Blue Harbor Resort and Conference Center

Shoreline Serenity - 2 Private Acres

10/10 Excellent

"Unique, interior revised design/layout. Views are a delight. Prep for visitors is very encompassing. Erin was very helpful."

William L. 4-night trip

Posted 10 days ago

Shoreline Serenity - 2 Private Acres

Find out more about Cleveland

Cleveland Holiday Homes information

Number of reviews	596
Accommodation	221 Holiday Homes
Lowest Price	£134
Highest Price	£832

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Cleveland on Expedia.com

Search Holiday Homes in Cleveland

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cleveland holiday homes

1. 3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

2. The Links! - Luxury Golf Retreat with Golf Simulator

3. The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

4. Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

5. New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

6. Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

7. Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

8. 1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

9. The Esker Ridge Chalet, Pristine Elkhart Solitude

10. Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

11. Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

12. Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

13. 3 Min to Road America, "Amazing Location!!"

14. Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

15. Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

16. Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

17. 5 min from Road America. Great yard and plenty of parking

18. Stunning private home hidden in the woods. Can sleep 11 guests

19. Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

Find holiday rentals that suit your style

Top Cleveland Hotel Reviews

Watershed Hotel

Find out more about Cleveland

Cleveland Holiday Homes information

Explore a world of travel with Expedia