Vacation rentals with a patio in Sheboygan

The perfect location!

You will be close to everything when you stay at this 1930s home. Walk three blocks west to Sheboygan's historic downtown to find shops, restaurants, theaters, museums, and a local farmer’s market. Walk two blocks east to the beach, walking/biking trail, marina, and parks. Free street parking, 1-stall attached garage, reliable wifi. All three bedrooms and full bathroom are upstairs. Washer/dryer and 1/2 bath are in the basement. Three window AC units in the summer. Kitchen has basic amenities.

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.

Vintage Farmhouse on Blueberry Hill.

Relax with the whole family at this peaceful place to stay. Located conveniently half way between Green Bay and Milwaukee. Find your self minutes away from Road America, Whistling Straits, snowmobile trails, kettle moraine state forest, and so much more. Our property has walking trails to the river, throughout the woods and around the creek area, This winter you would have the opportunity to snowshoe our 103 acre property, or break your own cross country ski trail! Or just a quiet getaway!

Bird's View King Suite

This upper unit is close to everything, making it easy to plan your visit to Sheboygan. It is fully stocked with everything you need while away from home. Spacious and clean with a dedicated workspace and fast internet. Enjoy some fresh air on the balcony or grill out in the beautiful yard below. The building has a shared laundry area in the basement with two new washers and dryers included for guest use. There is ample off street parking and a lovely green space with picnic table and grill.

New Listing: Private Lake Michigan beach home

Walk to your private beach without a bluff! Nestled between mature trees, Lakepines Cottage sits on 2 beautiful acres with over 200 feet of private beach. Offering breathtaking views of Lake Michigan, easy water access, flat lawn, walking trails through woods and prairies, and ample parking. This luxuriously appointed mid century modern home has everything you need just feet away from the beach. Lakepines Cottage is the perfect place to relax and make precious memories with your family.

Lovely modern two bedroom home with fire pit

Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. No smoking in the house. Ample street parking at the front door. Fire pit in back yard.

Crystal Cove - 2BR| Lake Views & Massage Chair

Crystal Cove by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. This lakeside condo boasts 2 bedrooms, 2 bathrooms, and a breathtaking view of Lake Michigan. Indulge in sunrise coffee overlooking the tranquil waters or sink your toes into the sandy shores mere steps away. Our pièce de résistance is a state-of-the-art full-body massage chair for ultimate relaxation.

Spacious Home Near Lake MI w/ Fire Pit

Welcome to the Relax ‘n Retreat! Retreat: noun - a quiet or secluded place in which one can rest and relax Unwind at our 3 bedroom home near Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening around the fire pit, or if you don’t feel like staying in, head out to discover some of Sheboygan’s many hidden gems. Send me a message to find out about our other available listings.