Vacation rentals in Winthrop Harbor

Bright, Airy SuperHost’s Kenosha Backyard Home

Newer, modern 4BR/2.5BA home in peaceful residential neighborhood. 10min from beautiful Kenosha beaches, Microsoft, UWP, Carthage, harbor market, museums, restaurants, & more! The house features 2 dining areas, dedicated office space, and a large unfenced backyard with relaxing patio seating. Very family friendly! Perfect for your family vacation, friends getaway or business trip -we are experienced hosts. Book with confidence! 30min to Milwaukee airport, 50min to O’Hare, 25min to Six Flags

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.

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.

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.

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

"Magnolia Farmhouse" inspired 4-bedroom home

Enjoy a spacious, open floor plan on a quiet, dead-end street! This "Magnolia Farmhouse" inspired 4-bedroom ranch home is set on one acre. Located 50 miles from Milwaukee, 45 miles from Chicago, and 2 miles from having your toes in the sand at Lake Michigan! Minutes away for the Great Lakes Naval Station (9mi) and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here, make Boyce Lane your home away from home today!

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).

The Victory Park Ranch - West

We are excited to welcome you to this comfortable and newly renovated modern house, in the perfect location if you're visiting Northern Illinois/Chicago. 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 definitely a place to check out! We are very close to Six Flags, Great Lakes Naval Base, and The Genesee Theatre too!

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!

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.

Your best choice* Cozy, spacious, comfortable, lg

Large, Cozy, suite w sweet kitchenette for “portable” meals; full-size refrigerator/ freezer; a writing desk for work. Many little ( in case you forgot) items to keep you comfy. This is a quiet town on the gorgeous Lake Michigan. Near: 6 Flags, Great Lakes Navy Base; Cancer Treatment Centers of America & the city Chicago via the Metra in town. Convenient & Quiet. I have 3 dogs. They are kind, outgoing and will want to meet you.

Lake Michigan Writer’s Cabin

Beautiful Lake Michigan retreat perfect for relaxing, boating, fishing, swimming and more! A true cabin experience. Perfect for ice fishing in the winter. A Sportsman’s paradise. Ideal for the adventurous. Relax, do some writing or work overlooking the breathtaking scenery. A stone's throw to the beach. Two decks overlooking the tranquil landscape. A short walk to downtown shops, cafes and restaurants.