Vacation rentals in Winthrop Harbor

Cozy Mother inlaw Suite. Private. Next to beach.

30 minutes away from the Navy Base(Graduates). 5 minutes away from the newly renovated Beach. 10 minutes to Wisconsin. 1 hour 40 minutes to O’Hare Airport and downtown Chicago. 40 minutes to Milwaukee Airport 25 minutes to Six Flags. This Mother in Law suite has tons of natural light. Private access and no shared indoor space. Safe and quiet neighborhood with plenty of wildlife right in the back yard. For nature lover’s this unit is close to the beach and there are walking trails nearby.

Unique Dome Home Golf Range Experience by the Lake

As featured in Golf Digest, this memorable place is anything but ordinary! Our spacious dome home is perfect for a quiet weekend away or hosting a large group of people. Located on a secluded driving range with your own private access and 1 mile west of Lake Michigan, our location is perfect! Beaches, parks and two golf courses all within 10 miles from the house! Here in the winter? No problem! We have ski hills all around us! Our home is the perfect place to resort to after a day on the slopes.

B’s Farmhouse Cottage 2-bedroom duplex.

Experience the best of the midwest! Recently remodeled in 2021 magnolia home inspired 2-bedroom duplex, all to yourself near everything you need. 50 Miles from Milwaukee, miles from Chicago, and 2 miles having your toes in the sand at Lake Michigan. We are minutes away from the Great Lakes Naval Station and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here make J&B's Farmhouse Cottage your home away from home today.

Bekahs Boho House

Make some memories at this unique family-friendly place located in a beautiful neighborhood steps away from Becker park. This location includes a private fenced in backyard, covered porch, fire-pit, and grill for enjoying outside activities. Central location to stores and 15 min from Renaissance fair! Private driveway and free street parking. Free wifi and Apple TV available. Per Airbnb policy we have outside surveillance cameras for safety purposes. No large parties allowed per Airbnb policy.

Cozy 2 bedroom home with a study

This newly remodeled chicken Coop turned into a 2 bedroom A frame home is fifty miles from Milwaukee, forty-seven miles from Chicago, and ten miles from the Naval Station. We are a couple minutes away from City of Hope, Six Flags Great America, Bristol Renaissance Faire, Great Wolf Lodge, Casinos, and the beach. There is also a Target and Starbucks down the road, what more can you ask for! The stairs to the bedrooms are steep and narrow so please be careful. Please enjoy the home to yourselves

Breathtaking view @lakefront

Breathtaking sunrise water views from every room! The house is only 40ft from the private sandy beach. Watch waves hit the rocks from the upper bedrooms. Moonlight reflecting off the water is priceless! Enjoy evenings by the wood fire pit or 10ft outdoor gas fireplace, four fireplaces inside including two in bedrooms. Take advantage of kayaks, basketball hoop, game room, nearby sand dunes, small beaches, cycling trails, nearby harbors for watercraft launches, hiking trail, steam sauna in shower

Downtown-Treetop Deck-2Bd/2Bth

Discover this one-of-a-kind, shabby-chic second-floor apartment in the heart of Downtown Kenosha — just steps from coffee shops, restaurants, museums, and the shores of Lake Michigan. Ideal for travelers who want everything within walking distance. Relax and unwind on the spacious, completely private back deck — your own hidden oasis tucked among treetops and historic neighborhood buildings. Perfect for stays up to four guests. Please note: This property is not suitable for young children.

Cute & Cozy, 1bd Condo Apartment/townhouse

Enjoy a stylish experience at this centrally-located place. Unique split-level 1-bedroom condo with modern upgrades, stainless steel appliances, LED lighting, but extremely comfortable amenities. Located minutes from Walmart, restaurants, the Cancer Treatment Center. Reasonable driving distance from Great Lakes Naval Base, Six Flags, Gurnee Mills Shopping Center, Casino, Milwaukee & Chicago. Sleeps 3 (queen bed with mood setting lights + sleeper sofa). May not be ideal if stairs are an issue

Wisconsin Treehouse Getaway!

Featured in Timeout Magazine as Chicago's Top 10 Airbnbs, and in other outlets as Wisconsin's most romantic and top 5 Airbnbs, this space has an immersive nature experience, overlooking a creek and woods with all modern comforts. Imagine yourself in a cabin in the woods to unplug and recharge, waking up to chirping birds as if in a Treehouse! 3 miles to Lake Michigan & dwntn. lf we're home, a complimentary Chai! Come, make lifelong memories at Racine's Best Kept Secret No local bookings.

Kalo House | Mid-Century Modern Retreat

A beautifully preserved mid-century modern home designed by noted architect Edward Humrich. The Kalo House blends iconic architecture with warm, curated interiors. Clean lines, expansive windows, and thoughtful design throughout. Peaceful and stylish, it’s the perfect retreat for design lovers visiting Chicago’s North Shore, Lake Michigan, or nearby Great Lakes Naval Station. Thoughtfully, curated and hosted with care…Perfect for Navy graduation stays and gathering families together.

Perfect Getaway- Fire Pit, Game room, Near Lake

Make this 5-bedroom, 3.5-bath home with an incredible fire pit in Kenosha, WI your stay for a great fall getaway. Perfect for your next family reunion and/ holiday gathering for your group or getaway. Fire-pit great for those chilly fall nights and perfect for grilling s’mores. Entertaining activities for kids and adults include a music room with several instruments, a recreational room in the basement, and outdoor enjoyment. Conveniently located 2 miles from Lake Michigan.

The Harbor House - Amazing!

The Harbor House is simply AMAZING! Set on over an acre, this private beautiful home is perfect for making beautiful family and group memories. The spacious interior features a great room as well as a separate family room. The expansive kitchen is fully equipped. Smart TV's in all BR's, the GR and FR. Full size washer and dryer. This home boasts an expansive private yard featuring plenty of outdoor seating with a gas grill and firepit. Ample parking. RV parking (50 amp).