Holiday Homes in Cleveland

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Cleveland and around

Cozy home near Lake Michigan. Easy drive to Green Bay, Door County & Sheboygan.
Outdoor dining

Cozy home near Lake Michigan. Easy drive to Green Bay, Door County & Sheboygan.

9.8 out of 10, Exceptional, (69)
"The place worked out perfect for our needs"
Cozy home near Lake Michigan. Easy drive to Green Bay, Door County & Sheboygan.
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Property grounds

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

10.0 out of 10, Exceptional, (26)
"Every thing was great. "
The price is €293
includes taxes & fees
6 Sept - 7 Sept
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
3 bedrooms, iron/ironing board, WiFi, bed sheets

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

10.0 out of 10, Exceptional, (1)
"Very clean and good location; nice place for our dog; we would definitely stay again if the opportunity presents itself."
The price is €189
includes taxes & fees
24 Aug - 25 Aug
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Exterior

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

10.0 out of 10, Exceptional, (107)
"Great place to hang out and relax. Everything was thought of, which made it easy to enjoy."
The price is €166
includes taxes & fees
14 Sept - 15 Sept
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Fridge, microwave, oven, stovetop

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful place! "
The price is €527
includes taxes & fees
28 Aug - 29 Aug
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (2)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Exterior detail

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

10.0 out of 10, Exceptional, (170)
"Back again for another visit, wonderful as usual. We love this house and the ownwrs hospitality! We will be booking again!"
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Smart TV

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

10.0 out of 10, Exceptional, (3)
"Coastal Comfort was very clean, pleasantly decorated and comfortable. It is within driving distance to the lake as well as restaurants in Sheboygan. Perfect stay for the two of us. "
The price is €175
includes taxes & fees
2 Sept - 3 Sept
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach
Fridge, microwave, oven, stovetop

Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach

10.0 out of 10, Exceptional, (36)
"Loved it. Cute place, good parking, close to everything."
The price is €369
includes taxes & fees
28 Aug - 29 Aug
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach
The Esker Ridge Chalet, Pristine Elkhart Solitude
Exterior

The Esker Ridge Chalet, Pristine Elkhart Solitude

10.0 out of 10, Exceptional, (58)
"Wonderful place, so quiet and nature surrounding the location. So close to Elkhart Lake and yet you wouldn't realize it when on the property. Five Stars!"
The price is €241
includes taxes & fees
19 Aug - 20 Aug
The Esker Ridge Chalet, Pristine Elkhart Solitude
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Property grounds

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

9.8 out of 10, Exceptional, (31)
"This is our 4th year staying at this great property!"
The price is €423
includes taxes & fees
20 Aug - 21 Aug
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Executive Beachfront Villa: Sleeps 8!
Fridge, microwave, oven, stovetop

Executive Beachfront Villa: Sleeps 8!

2.0 star property
9.0 out of 10, Wonderful, (2)
"The home was great. The location was great. It was perfect for a night up at blue Harbor area to enjoy the restaurants and coffee shops."
Executive Beachfront Villa: Sleeps 8!
Stunning private home hidden in the woods. Can sleep 11 guests
Dining

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

10.0 out of 10, Exceptional, (10)
"This VRBO was everything that the listing described and more. The host was very easy to communicate with and helped make sure we had a great stay."
The price is €610
includes taxes & fees
19 Aug - 20 Aug
Stunning private home hidden in the woods. Can sleep 11 guests
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (32)
"The space and location were great! Communication was quick and thorough. "
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Beautiful Historic Home near Downtown
Dining

Beautiful Historic Home near Downtown

9.8 out of 10, Exceptional, (8)
"A gorgeously designed, spacious and well-appointed house. Convenient to a bunch of small Wisconsin towns and activities. Don’t sleep on the Hamilton Type Museum! "
Beautiful Historic Home near Downtown
Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.
Interior

Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.

9.8 out of 10, Exceptional, (149)
"Very clean and beautiful deck with views of Lake Michigan."
The price is €494
includes taxes & fees
7 Sept - 8 Sept
Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.
Road America, Elkhart Lake!
Terrace/patio

Road America, Elkhart Lake!

Road America, Elkhart Lake!
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
Fridge, microwave, oven, stovetop

Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.

10.0 out of 10, Exceptional, (10)
"Great house, great location, very well taken care of and meticulous accommodations. Definitely recommend and would stay again."
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
Just Beachy: 4 Bedroom, Sleeps 12!
Beach nearby

Just Beachy: 4 Bedroom, Sleeps 12!

10.0 out of 10, Exceptional, (2)
"Nice property with plenty of room for eight adults. Easy walk to Lake Michigan, restaurants and coffee shops. "
The price is €701
includes taxes & fees
1 Sept - 2 Sept
Just Beachy: 4 Bedroom, Sleeps 12!
5 min from Road America. Great yard and plenty of parking
Fridge, microwave, oven, stovetop

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

The price is €1,028
includes taxes & fees
28 Aug - 29 Aug
5 min from Road America. Great yard and plenty of parking
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

Watershed Hotel

10/10 Excellent
"Always a warm welcome.. special call out to Chris on reception. Will return on next Sheboygan trip."
Lee 1-night trip
Posted 2 days ago
Watershed Hotel