Vacation rentals in Cleveland

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Top-rated vacation rentals in Cleveland

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

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Top guest favorite
Home in Cleveland
5 out of 5 average rating, 5 reviews

Shoreline Serenity

Welcome to ''Shoreline Serenity''! 200 ft of Lake Michigan frontage w/unobstructed views that go on for miles and tucked away on a 2-acre lot offering peace & privacy. Inside the home, you will be drawn to the beautiful views through the full wall of east facing windows & patio doors. The interior is cozy, clean, and comfortable. Fully equipped kitchen w/coffee bar. Main level has (2) bedrooms including the primary bedroom w/fantastic views. The spacious upper level loft has a king & twin bed.

Top guest favorite
The A-frame cabin is framed by lush greenery and colorful landscaping. A welcoming pathway leads to the entrance, featuring a spacious deck. The cabin's dark exterior contrasts with the surrounding trees, creating a serene and private atmosphere.
Cabin in Elkhart Lake
4.99 out of 5 average rating, 348 reviews

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

Top guest favorite
A single-story ranch home is depicted, showcasing a well-manicured lawn with green grass and various shrubs. The exterior features a blend of siding and brick, with large windows providing ample natural light. A two-car garage is present on one side of the home.
Home in Manitowoc
4.91 out of 5 average rating, 173 reviews

Neighborhood home in Manitowoc

Guests must check-in in person. 4 bedroom ranch home with deck and backyard in a pleasant neighborhood with sidewalks. 3 full bathrooms, one with an oversized jacuzzi tub. Large entertaining areas both on the main floor and the fully finished basement with wet bar, wine cellar and waterfall feature. There’s two fireplaces and an outdoor fire pit. This house is not suitable for children between the ages of 2 and 12. No internet. Easy access to I-43 approximately 25 miles to Green Bay or Kohler.

Top guest favorite
A single-story house with a neatly maintained lawn and vibrant flower beds welcomes visitors. An American flag is displayed at the entrance. The driveway leads to a garage on the left side of the house, and ample green space surrounds the property.
Home in Howards Grove
4.96 out of 5 average rating, 201 reviews

Spacious lower level priv entrance no cleaning fee

Not set up for babies or toddlers. 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.

Guest favorite
An inviting wellness space features a hot tub with gentle bubbles and soft green lighting. Adjacent, a wooden dry sauna awaits, surrounded by potted plants. Comfortable seating with decorative pillows is arranged nearby, creating a serene atmosphere for relaxation.
Home in Sheboygan
4.97 out of 5 average rating, 270 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Celebrate your special occasion in Sheboygan at this beautiful boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom w/King size bed. Secondary bedroom has 2 twin beds. The beautiful fireplace in the living room is perfect for a relaxing couples evening. Enjoy a glass of wine or local brew on the patio while you grill out. EV Charger and E-Bikes to explore the area. Let us impress you and help make it a memory.

Top guest favorite
An aerial view of a spacious home is surrounded by mature trees, showcasing a private sandy beach alongside Lake Michigan. The property features a pathway leading to the house, emphasizing its secluded setting amid natural greenery.
Home in Oostburg
4.96 out of 5 average rating, 179 reviews

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.

Guest favorite
An aerial view captures the layout of the property, showcasing a cluster of buildings surrounded by lush greenery and a small pond. Farm fields extend in all directions, while trees add a touch of vibrant color to the landscape.
Barn in Sheboygan Falls
4.73 out of 5 average rating, 151 reviews

Quiet Country Charm

Cozy barn loft with rustic charm. This newly renovated private loft sleeps 4 with the possibility of 1 or 2 more if you don’t mind sleeping on an air mattress. This room includes a bathroom with shower and small efficiency kitchen with microwave, coffee maker, and small refrigerator. The futon pulls out to a double bed. This relaxing local comes complete with barnyard animals for an authentic Wisconsin experience! You won’t forget the peaceful surroundings of this rustic destination.

Top guest favorite
Cabin in Cascade
5 out of 5 average rating, 265 reviews

hot tub and sauna on 5 private acres

Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

Top guest favorite
A neatly arranged countertop displays a candle labeled 'Blush Floral' alongside a clear vase filled with fresh red roses. A sleek soap dispenser, marked 'Church Street Hand Soap,' sits prominently, enhancing the serene ambiance of the space.
Apartment in Kohler
5 out of 5 average rating, 218 reviews

Church Street Romance & Retreats-Village of Kohler

“A well-appointed, cozy and stylish retreat close to everything in Kohler.” -Kim Take the stairs to my secluded 2nd floor tree view retreat! A private side entrance and open floor plan flanked by two bedrooms makes this unit perfect for couples or a girl's getaway spa weekend. Romantic turn-of-the-century touches meet modern convenience & comfort. Baker furniture, previously a Kohler Company, can be found throughout the apartment enhancing your Village of Kohler stay.

Top guest favorite
A modern single-story home features a light gray exterior with a striking yellow front door. Large windows provide abundant natural light, while a well-maintained lawn is complemented by colorful flower beds. Skylights on the roof enhance the home's contemporary design.
Home in Cleveland
4.96 out of 5 average rating, 157 reviews

Guest Favorite | Super Host + Clean & Modern Stay!

Unwind in this modern retreat just minutes from Whistling Straits Golf, Road America, Lake Michigan, and year-round outdoor adventures. The bright, open living spaces feature high ceilings, skylights, and stylish furnishings, with thoughtful comforts like heated bathroom floors. Enjoy the spacious outdoor living area for relaxing after a day out. Ideal for golfers, couples, families, wedding groups, business travelers, and traveling nurses.

Top guest favorite
A spacious living area is centered around a circular glass table with a potted plant. Comfortable gray sofas frame the space, accompanied by two blue chairs. A stone fireplace adds warmth, and large windows allow natural light to fill the room, displaying views of the outdoors.
Home in Cleveland
4.99 out of 5 average rating, 88 reviews

Lake Michigan Views | 4BR Near Whistling Straits

Summer on Lake Michigan starts here! Enjoy sweeping lake views from this light-filled 4-bedroom retreat. 3 bedrooms overlook the water. Relax by the fire pit to the sound of waves, dine indoors or on the patio, and take in unforgettable sunrises. Located just 4 minutes from Whistling Straits, 4 minutes by car to beach access and a short drive to Kohler and Sheboygan—This home is perfect for golf trips and family vacations.

Top guest favorite
Home in Cleveland
4.98 out of 5 average rating, 81 reviews

Hidden Haven - Modern Cottage w/ Hot Tub & Views

Hidden Haven by Great Lakes Getaways! Discover our new modern cottage on Lake Michigan’s coast, nestled on a spacious 3.5-acre lot. Outdoors, unwind in the seven-person hot tub or enjoy the expansive backyard. Inside, every room offers stunning views and tranquil scenes, complemented by modern amenities and stylish decor. Perfect for a serene escape, this cottage promises a blend of luxury and nature.

Popular amenities for Cleveland vacation rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Manitowoc County
  5. Cleveland