Holiday houses in Winthrop Harbor

Stunning Home Across The Street From North Beach

Newly remodeled home on Michigan Blvd. We went the extra mile in creating this beautifully curated, lush, and stylish home! Kick back and relax in one of the many thoughtfully designed rooms and the huge front outdoor deck with amazing views of Lake Michigan! Anywhere you gaze, you will find a visually stimulating experience in this home! Across the street from Lake Michigan, North Beach, and Kids Cove Playground. Short walk to Racine Zoo, the Marina, downtown Racine shops and restaurants.

B’s Farmhouse Cottage 2-bedroom duplex.

Experience the best of the midwest! Enjoy a newly remodeled "Magnolia Farm" 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.

Nonsmoke, No Cleaning Fees, No Long Chore Lists.

25 minutes away from the Naval Station 5 minutes away from the 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 and Great Wolf Lodge. Safe and quiet neighborhood with plenty of wildlife right in the back yard. This Mother in Law suite has tons of natural light. For nature lover’s this unit is close to the beach and there are walking trails nearby. Small children maybe heard from 7AM to 8PM.

Tiny home in not so tiny Yard

The house has a Queen bed, a Single bed and a sofa. A tiny home in a peaceful neighborhood. Built on 4 city lots, it has plenty of space and privacy. For families visiting the Naval Academy, we are close enough, yet give you space and privacy. Away from the hustle of North Chicago and Waukegan. Nearby attractions are: Naval Base - 11 miles, 20 minutes Six Flags - 7 miles, 15 minutes Illinois State Beach - 2 miles, 5 minutes Chicago - 46 miles, 60 minutes Milwaukee - 50 miles, 55 minutes

The Indigo Cottage

This is a newly remodeled single-family home! It is small but has everything you need to enjoy time with family and friends during your stay in the Chicagoland area! There are two bedrooms each with a queen bed, an updated bathroom, a dining room with seating for 6, a cozy living room with a Crate & Barrel pull-out queen sofa bed, and a nice, updated kitchen! There's a brand-new washing machine and dryer in the basement. There's a nice patio table outside too in the private yard. Welcome!

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. And if we're home, a complimentary Chai for you! Come, make lifelong memories at Racine's Best Kept Secret!

Kenosha! Enjoy your stay as you work or play!

Soft towels, fluffy pillows, complimentary breakfast, soft drinks, and more in a safe and secure environment. Only children over 13 allowed and must be accompanied by an adult. This n-smoking, pet-free 1-bedroom w/king bed, twin mattress daybed and cot, furnished kitchen and bath apartment is on the 2nd floor of an office building. Free HI-SPD Wi-Fi and big screen Smart TV. Access to museums, universities, shopping, Chicago’s METRO train and only 37 miles from downtown Milwaukee!

This one feels like Home

Relax at this peaceful place to stay. Located on dead end st and Sleeps 6 with finished basement. 2 bedrooms on main floor, 3rd bed and tv rm in bsmt.. Small galley kitchen , and bath is compact. Please no cats , dogs under 30 pounds . Sparkling clean & just minutes from Lake Michigan. try HEBREWS COFFEE SHOP AND STONE CREEK STEAK HOUSE . Located right in the middle of Milwaukee and Chicago. 17 minutes from Great Lake Naval Base and just minutes from Hope Cancer Hospital.

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

The Office Loft

We are very excited to welcome you to this comfortable and high-quality, modern apartment, in the perfect location if you're visiting Northern Illinois. Come see why Waukegan is nicknamed "Green Town" and is home to some of the finest parks, ravines, and walking trails. With an incredible sandy beach, lakefront, galleries, breweries, restaurants, and more, it is a place to check out! We are very close to Six Flags, Great Lakes Naval Base, and The Genesee Theatre too!

Amiable 1-Bedroom 2-beds - 1 Bath - Apartment

Step into comfort in this thoughtfully furnished 1-bedroom apartment in Waukegan, Illinois. Perfect for business travelers, visitors, or those in between moves — this unit hits the sweet spot of style, function, and value. The Space One bedroom with a full/queen bed plus an air mattress (for extra comfort or guest flexibility) Bright living area with seating, smart TV, and workspace Fully equipped kitchen (stove, refrigerator, microwave, basic cookware & utensils)

Lovely home near the beach in a safe neighborhood

Our simple, yet welcoming property is minutes away from beaches, downtown, minor league baseball, the farmers market, and many delicious restaurants, as well as having close proximity to Carthage College, 6 Flags, and a quiet 30 min drive to Great Lakes Naval Base. We are located in the Allendale neighborhood boasting a family-friendly atmosphere on a quiet street. Whether you are here to relax, have fun, or attend special events, our house can provide.