Holiday rentals in Winthrop Harbor

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.

Relaxing beach-style sanctuary in quiet area!

Cozy brick ranch in quiet neighborhood, 2 blks from Jewel, Dunkin Donuts, Walgreens, Etc. Gas fireplace, wifi, smart tv, heated bathroom floor, treehouse deck, private backyard landscaped sanctuary, attached garage. Easy access to Lake Michigan, less than a mile from City of Hope, formerly CTCA; the Wisconsin state line; midway point between Chicago and Milwaukee; Great America and Gurnee Mills; and Great Lakes Navy Base. LOTS to do in the area!!! Price reduced for winter due to -1 bedroom.

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

J’s Farmhouse Cottage. 2 bedroom duplex.

Formerly known as Magnolia Farmhouse inspired. 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, 45 miles from Chicago, and 2 miles from having your toes in the sand at Lake Michigan! We are minutes away from the Great Lakes Naval Station (9 mi) and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge.

Historical Hideaway near Naval Base

Step back in time at The Pilothouse, a charming historic 1854 home located in Waukegan’s historical district, just 12 minutes from Naval Station Great Lakes. This beautifully preserved home features Navy and aviation-themed décor, 3 cozy bedrooms, a sunroom filled with lush plants, a fully equipped kitchen, and a spacious backyard with a gazebo, large patio, and grill—ideal for relaxing outdoors. Experience the perfect blend of vintage charm and modern comfort in this serene retreat.

Minutes from naval base casino and six flags

Your family will be close to everything when you stay at this centrally-located place. Naval base and six Flags great America and NEW CASINO are just down the road less than 10 minutes . We are only about 45 min from downtown chicago. About 35 from O’Hare. And less than 10 from Gurnee mills. Plenty of restaurants within minutes and Starbucks is only 3 minutes away. 10 mins from Waukegan beach The house sits on 3 property lot, so it’s very private with no real next door neighbors.

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).

Designer luxury loft in perfect downtown location

Escape to our spacious and luxurious designer open-space loft with panoramic downtown views through our giant windows. Whip up your favorite meals in our modern kitchen with modern stainless-steel appliances and plenty of storage space. A cozy and comfortable bed, smokeless fireplace, and ample walk-in closet ensure a clutter-free and restful environment. Treat yourself to a rain shower in any of the two bathrooms, complete with luxurious features like towel and mirror warmers.

Cozy mother inlaw suite. Private. Next to beach.

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.

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!

Harbor Haven/Near Base/Great America/Game Room/Gym

Welcome to your perfect escape near the shores of Lake Michigan! Located in a quiet, safe neighborhood, our spacious 3-bedroom, 2-bath home offers comfort and convenience. Enjoy a fully equipped kitchen, king- and queen-size beds, and a fenced yard ideal for families. Just 1.5 miles from the water and minutes from the Great Lakes Naval Station, we proudly host military families visiting for graduations, training, and reunions. A warm, welcoming place to feel at home.

Little House by the BIG LAKE

Only steps away from Lake Michigan, our well-appointed home is your southeast Wisconsin retreat. The home is in a peaceful, safe neighborhood, less than 2 blocks from the Eichelman scenic park/beach. Kenosha's downtown which is loaded with fun shops, restaurants, cafes and breweries is a short walk away. Take a stroll to the harbor, lighthouse, Civil War Museum, and marina. Great Lakes Naval Station is 1/2 hour down the lakefront.