Vacation rentals in Winthrop Harbor

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Top-rated vacation rentals in Winthrop Harbor

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Top guest favorite

Guest suite in Zion

4.9 out of 5 average rating, 223 reviews

Nonsmoking, no cleaning fees, mother-in-law suite.

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.

Top guest favorite

Apartment in Kenosha

4.99 out of 5 average rating, 190 reviews

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.

Guest favorite

Apartment in Kenosha

4.97 out of 5 average rating, 37 reviews

Blue Sky Landing

Enjoy a comfortable stay at this centrally-located studio.Walking distance to popular restaurants/ taverns, Downtown and Lake Michigan.Separate private entrance for all units. Kitchenette with microwave, airfryer and toaster plus fully stocked cabinets for everything you need to stay in and enjoy meals.Water cooler with hot/cold water and Keurig coffee maker with a selection of premium coffees and teas.Nice size bathroom with shower and jacuzzi bath. Salon quality Shampoo/Conditioner provided

Guest favorite

Guest suite in Riverwoods

4.96 out of 5 average rating, 425 reviews

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.

Guest favorite

Tiny home in Beach Park

4.84 out of 5 average rating, 119 reviews

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

Top guest favorite

Apartment in Beach Park

4.97 out of 5 average rating, 425 reviews

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.

Guest favorite

Apartment in Kenosha

4.94 out of 5 average rating, 118 reviews

Kenosha! Work or play, enjoy your stay!

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/queen 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!

Top guest favorite

Home in Winthrop Harbor

4.96 out of 5 average rating, 28 reviews

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).

Top guest favorite

Home in Pleasant Prairie

5 out of 5 average rating, 69 reviews

Beach House Retreat with Firepit and Game Room

Our beach home is just across from Lake Michigan and a 4-minute walk to the public beach, set on 1.5 acres of lush greenery and mature trees. Chicago and Milwaukee are about an hour away; the Navy Base is 30 minutes. Enjoy the fire pit, outdoor games, or game room, cook in a well-equipped kitchen, and sleep soundly on memory foam beds with high-thread-count sheets. Nearby: golf, shopping, trails, restaurants, bars, and family-friendly fun.

Guest favorite

Apartment in Winthrop Harbor

4.94 out of 5 average rating, 310 reviews

Calm here! Cozy, spacious, comfortable, lg space

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.

Guest favorite

Home in Winthrop Harbor

5 out of 5 average rating, 32 reviews

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

Welcome to your perfect escape near the tranquil shores of Lake Michigan! Nestled in a serene neighborhood, our spacious 3-bedroom, 2-bath house offers the ideal blend of comfort and convenience. Enjoy fully equipped kitchen, cozy bedrooms with king and queen size beds, and a beautiful fenced yard. Just 1.5 miles from the water, it's the ideal spot for local explorations. Come and create lasting memories in this delightful house.

Top guest favorite

Cabin in Kenosha

4.83 out of 5 average rating, 686 reviews

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.