Vacation rentals in Cleveland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Cleveland

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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.

Guest favorite

Cottage in Oostburg

4.97 out of 5 average rating, 231 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.

Guest favorite

Castle in Cleveland

5.0 out of 5 average rating, 98 reviews

Castle Vineyard – Spa, Theater, Golf Sim, Weddings

As seen on the cover of Haven, a luxury home magazine! This masterpiece was built over the course of seven years and is officially open to the public in 2022! For travelers who want an exclusive taste of Tuscany without the hassle of jetting across an ocean, "The Castle Vineyard" is the place to stay. The dramatic, spellbinding stone castle proudly overlooks over twenty acres of idyllic rolling hills and a gorgeous, working vineyard. Once inside, the interior does nothing to dispel the magic.

Guest favorite

Home in Newton

5.0 out of 5 average rating, 23 reviews

Lake Home with Sweeping Views of Lake Michigan.

Located on a bluff overlooking Lake Michigan with beach access this house is the place to unplug and unwind. Conveniently located off Lakeshore Drive we are centrally located to the two great port cities of Manitowoc and Sheboygan. Over an acre of outdoor green space to enjoy along with steps off the bluff leading down to a sand beach. Relax on adirondak chairs around the outdoor firepit, enjoy morning coffee in the sunroom while the sun rises or simply enjoy the 3000 sq feet of living space.

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.

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!

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).

Guest favorite

Cottage in Fond du Lac

4.97 out of 5 average rating, 234 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.

Guest favorite

Home in Plymouth

4.97 out of 5 average rating, 164 reviews

Wyatt's Country Home - King Bed!

Soak up the modern vintage charm of our fully remodeled and updated home! Thank you for choosing our sparkling clean space. Our home is nestled on two quiet acres just north of Plymouth in the peaceful country. Enjoy coffee as the sun rises from one of the two decks, or perhaps a cocktail by the fire as the sun sets. We ourselves lived in this home for our first 5 years and turned it into a beautiful and peaceful space for ourselves that we would now like to share with everyone.

Guest favorite

Apartment in Sheboygan

4.92 out of 5 average rating, 394 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.

Guest favorite

Cottage in Manitowoc

4.88 out of 5 average rating, 123 reviews

Year Round Home on English Lake in Manitowoc Cty

Lovely year round home on English Lake in Manitowoc county. Non motorized boats are available during the summer. 25 miles from Kohler resort. 45 minutes away from Green Bay Packers and 75 miles north of Milwaukee. For winter arrival, you do need to have an all wheel or 4 wheel drive. There are two hills that can be tricky without these! If you are looking for a date that is blocked out, please inquire as we may be able to open up more dates.

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

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

Townhouse in Sheboygan

4.94 out of 5 average rating, 81 reviews

Danz Sheboygan Retreat. Newly Remodeled in 2021.

Guest favorite

Home in Reedsville

4.98 out of 5 average rating, 41 reviews

Newly remodeled farmhouse, quiet, comfy, and cozy.

Guest favorite

Apartment in Manitowoc

4.91 out of 5 average rating, 74 reviews

Lower Apt steps from Downtown and the Lake!

Guest favorite

Guest suite in Sheboygan

4.92 out of 5 average rating, 66 reviews

Cozy 1BD RM W/ fireplace by lake

Guest favorite

Cabin in Valders

4.97 out of 5 average rating, 32 reviews

Cozy cabin in the woods

Superhost

Apartment in Sheboygan

5.0 out of 5 average rating, 3 reviews

Modern Lower Apt - One block to the Lake

Guest favorite

Home in Manitowoc

4.89 out of 5 average rating, 57 reviews

Modern 2 Bedroom House, Close to Lake Michigan

Guest favorite

Home in Sheboygan

5.0 out of 5 average rating, 46 reviews

3-Bedroom House with Attached Garage

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
$140 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

Townhouse in Sheboygan

Home in Reedsville

Apartment in Manitowoc

Guest suite in Sheboygan

Cabin in Valders

Apartment in Sheboygan

Home in Manitowoc

Home 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?

Destinations to explore