Vacation rentals in Winthrop Harbor

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.

Cozy 2 bedroom home with a study

This newly remodeled chicken coop turned into a 2 bedroom A frame home is 50 miles from Milwaukee, 47 miles from Chicago, and 10 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, American Place Casino, 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

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.

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

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.

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, plus four more 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, and hiking trails.

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).

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.

6th Ave Harborside

Perfectly located near downtown Kenosha, this cozy and comfortable home makes it easy to enjoy the best of the area. Ride the bikes to the farmers market, stroll to the beach, or spend time along the marina and harbor. The large dining room invites long meals and relaxed evenings together. An ideal home base for a peaceful getaway, visiting family, or attending local events. One night stays are available on a limited basis - reach out for details!