Vacation rentals in Cleveland

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Top-rated vacation rentals in Cleveland

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Guest favorite

Home in Howards Grove

4.95 out of 5 average rating, 151 reviews

Spacious lower level priv entrance no cleaning fee

Entire basement is for rent with a separate entrance. Kitchen area includes refrigerator, microwave, coffee pot, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee. Unit NOT set up for babies or toddlers.

May 3 – 10

R2,080 ZAR per night

Guest favorite

Cottage in Oostburg

4.97 out of 5 average rating, 232 reviews

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

Feb 15 – 22

R2,909 ZAR per night

Guest favorite

Home in Cleveland

4.83 out of 5 average rating, 12 reviews

Private lake home near Whistling Straits Kohler

Walk to your private beach without a bluff! Lakeglass Cottage is situated on 5 beautiful acres with over 300 feet of private beach. Offering breathtaking views of Lake Michigan, easy water access, 2 acres of flat lawns, walking trails through woods and prairies, and ample parking. This luxuriously appointed mid century modern home has everything you need and is just feet away from the beach. Lakeglass Cottage is the perfect place for you to relax and make precious memories with your family.

Oct 14 – 21

R9,244 ZAR per night

Guest favorite

Townhouse in Sheboygan

4.97 out of 5 average rating, 117 reviews

Family Friendly Riverfront Escape|HUGE Game Room

Welcome to The WAVE – your ideal family friendly retreat nestled along the scenic Sheboygan River, just minutes from the beaches of Lake Michigan. As you step into The WAVE, you'll be greeted by a tastefully designed interior featuring LUX furnishings that exude both style and coziness. The accommodations include a King Suite with a riverfront balcony and a Guest Room with 2 queen beds. Entertainment is taken to a whole new level with our 500 sq ft game room with a 130-inch projection screen.

Nov 29 – Dec 6

R2,339 ZAR per night

Guest favorite

Home in Cleveland

4.97 out of 5 average rating, 36 reviews

Lake Michigan Views minutes to Whistling Straights

Soak up the Wisconsin Summer in this beautiful home with breathtaking views of Lake Michigan. This spacious home is showered with natural light and 3 of the 4 bedrooms have brilliant lake views. Enjoy family or holiday meals in the formal dining room or outdoors on the patio. Take in the calming sound of the waves while relaxing by the fire pit with friends. Located just minutes from Whistling Straights, Sheboygan, and Kohler, there is no better place to bring the whole family for your trip!

Jun 9 – 16

R6,378 ZAR per night

Guest favorite

Home in Cleveland

4.95 out of 5 average rating, 131 reviews

Modern Home Just 5 Minutes from Whistling Straits

My home is just minutes from Whistling Straits Golf, Road America, Lake Michigan, Parks, Hiking, Biking, Snowshoeing, and Cross Country Skiing. You’ll love my place as it's newly remodeled, modern & cozy. The kitchen and living areas have high ceilings, sky lights & new furniture. The large outdoor living area is perfect for social time. My favorite is the heated bathroom floors. My place is perfect for golfers, wedding groups, couples, business travelers, and families (with kids & dogs).

Sep 23 – 30

R4,061 ZAR per night

Guest favorite

Cottage in Fond du Lac

4.97 out of 5 average rating, 235 reviews

Cozy Guest House with Lake views.

Our remodeled two bedroom Guest House is adjacent to our Cottage and offers beautiful lake views. Access to Lake Winnebago available at near by boat launches. Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen bed and 2 twin beds, 1 full bathroom, and a fully stocked newly remodeled kitchen. Perfect getaway for some R&R with family or friends.

Sep 22 – 29

R1,250 ZAR per night

Guest favorite

Home in Sheboygan

4.97 out of 5 average rating, 151 reviews

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

Jun 22 – 29

R2,956 ZAR per night

Guest favorite

Apartment in Sheboygan

4.92 out of 5 average rating, 397 reviews

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

Feb 2 – 9

R1,577 ZAR per night

Guest favorite

Home in Glenbeulah

4.98 out of 5 average rating, 111 reviews

Stay at Sunrise LLC, Like being at Grandma's

Welcome to Stay at Sunrise LLC. We offer a clean and comfortable home for your vacation enjoyment. We are in a rural farm area, the recreation trail head is 3 miles east of us as well as the Wade House, we are near the Kettle Moraine State Forest and the Ice Age Trail and 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. Smoking is allowed outside of the home. No pets allowed.

Dec 27 – Jan 3

R1,656 ZAR per night

Guest favorite

Apartment in Sheboygan

4.84 out of 5 average rating, 183 reviews

Sheboygan Surf House "Jetties"

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our Urban living oasis is a fully equipped studio apartment conveniently located in the heart of downtown, just steps from bars and restaurants and only blocks to Lake Michigan South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake, Kite boarding, charter fishing, a Wedding or leisure time SSH is perfect for you. Support Dog friendly

Sep 17 – 24

R1,257 ZAR per night

Superhost

Guesthouse in Sheboygan

4.83 out of 5 average rating, 367 reviews

Carriage House Sheboygan, Lake Mich beach access!

The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!

Mar 22 – 29

R2,006 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Cleveland vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Cleveland

Guest favorite

Home in Newton

5.0 out of 5 average rating, 23 reviews

Lake Home with Sweeping Views of Lake Michigan.

May 8 – 15

R8,485 ZAR per night

Guest favorite

Apartment in Manitowoc

4.91 out of 5 average rating, 75 reviews

Lower Apt steps from Downtown and the Lake!

Feb 19 – 26

R1,134 ZAR per night

Guest favorite

Home in Sheboygan

5.0 out of 5 average rating, 46 reviews

3-Bedroom House with Attached Garage

Sep 7 – 14

R3,491 ZAR per night

Guest favorite

Home in Reedsville

4.98 out of 5 average rating, 41 reviews

Newly remodeled farmhouse, quiet, comfy, and cozy.

Dec 31 – Jan 7

R2,333 ZAR per night

Guest favorite

Cabin in Newton

5.0 out of 5 average rating, 13 reviews

Modern Country Retreat

Mar 14 – 21

R4,020 ZAR per night

Guest favorite

Townhouse in Sheboygan

4.94 out of 5 average rating, 81 reviews

Danz Sheboygan Retreat. Newly Remodeled in 2021.

Nov 10 – 17

R1,885 ZAR per night

Guest favorite

Apartment in Sheboygan

5.0 out of 5 average rating, 88 reviews

Modern Upstairs Apt - Steps from Lake Michigan

Mar 12 – 19

R2,534 ZAR per night

Guest favorite

Cottage in Sheboygan

5.0 out of 5 average rating, 68 reviews

Cozy one bedroom cottage near lake Michigan!

Aug 15 – 22

R2,619 ZAR per night

Show all

Quick stats about vacation rentals in Cleveland

Total rentals
10 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
220 reviews
Nightly prices starting at
R2,687 ZAR before taxes and fees

Frequently Asked Questions

Do house rentals in Cleveland have wifi?
Absolutely! We offer over 10 house rentals with wifi in Cleveland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cleveland have free parking?
Absolutely! We offer over 10 house rentals with free parking in Cleveland. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Cleveland?
Cleveland has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Cleveland?
Experience the best of Cleveland with our house rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Cleveland have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Cleveland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cleveland have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Cleveland. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Cleveland

Top-rated vacation rentals in Cleveland

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Cleveland vacation rentals

Other great vacation rentals in Cleveland

Home in Newton

Apartment in Manitowoc

Home in Sheboygan

Home in Reedsville

Cabin in Newton

Townhouse in Sheboygan

Apartment in Sheboygan

Cottage in Sheboygan

Quick stats about vacation rentals in Cleveland

Total rentals

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Cleveland have wifi?

Do house rentals in Cleveland have free parking?

Are there family-friendly vacation rentals in Cleveland?

How much does it cost to stay in house rentals in Cleveland?

Do house rentals in Cleveland have air conditioning?

Do house rentals in Cleveland have a kitchen?

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