Holiday rentals in Cleveland

Castle Vineyard | Luxe Spa • Golf Sim • Theater

Stay at one of the most Wishlisted Airbnbs in the world. Featured in Men’s Health and on the cover of Haven magazine, The Castle Vineyard is a world-class destination 🍇 20-acre estate w/ vineyard, spa, & sauna 🎬 Private theater, arcade, PS5 & golf simulator 🍽️ Chef’s kitchen w/ Viking appliances 🔥 Fire pit, patio, hot tub, wildlife views 🏰 "Felt like royalty... every detail was magical" 🎉 Entire property is yours — guests may inquire about our exclusive Tasting Room for special events

House Near the Lake

Get out and enjoy nature, then return to a quiet mix of modern and retro in this family home only a block away from Lake Michigan. There are three parks and two beaches within a mile, as well as Terry Andrae State Park about 10 minutes away. If the outdoors aren't your thing, downtown Sheboygan hosts the Kohler Art Center, The Weil Center, Blue Harbor, and the Children's Museum, with Road America only 30 minutes away. Located between Milwaukee and Green Bay, this home has all the conveniences.

The Hemingway on Church - It Tolls For Thee

"Kristine's property has all the charm of a modern day Mayberry" -Michael This 1906 historic home is nestled in the heart of the equally historic "Village of Kohler." Completely remodeled in 2019 adding Kohler spa amenities and modern touches to its original charm. Mixing modern & antique furniture finds like the Hemingway Sideboard (which inspired the literary theme) make this historic hideaway a true Kohler destination. "You cannot get a better location in Kohler than this house!" -Dennis

Modern Home Just 40 Minutes from GB NFL Draft

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).

Camp Skywood - Elkhart Lake - Road America

Nestled just minutes from Downtown Elkhart Lake, this custom-built cordwood home offers a secluded sanctuary experience. Perched atop a hill, the unique 16-sided house provides breathtaking views of the state forest and surrounding farmland. Despite its remote feel, you’re only a 5-minute drive from the charming Elkhart Lake business district. Day hikes on the ice age trail are just steps away from the property. Escape to tranquility while staying conveniently close to local attractions.

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.

hot tub and sauna on 5 private acres

Need 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 inspired getaway awaits!

Boutique Wellness Retreat - Hot Tub and Fireplace

Enjoy this beautifully boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom with 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. Sonos audio throughout. This beautiful boutique home is sure to impress!

Lakeshore Bungalow Boutique

Newly remodeled upstairs 2 bedroom, very spacious apartment. Shaby sheek style downtown very cute home away from home. Just minutes from beautiful biking and walking trails and beaches along the beautiful shores of Lake Michigan. Walking distance to restaurants, pubs, wine bar, museums, beaches, shopping, grocery store, bakerie, zoo, car ferry, gym's, coffee shops, library. Beautiful lake Michigan Marina and Light House, Manitowoc is a very cute and quaint small town.