Holiday rentals in Winthrop Harbor

5 out of 5 average rating, 19 reviews

Flat in Kenosha

Blue Sky Landing

Enjoy a stylish experience 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

4.98 out of 5 average rating, 222 reviews

Home in Beach Park

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.

4.89 out of 5 average rating, 200 reviews

Guest suite in Zion

Non-smoking, attached 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 7PM.

4.98 out of 5 average rating, 132 reviews

Cabin in Castle Manor

A Frame Log Cabin Near Multiple Local Lakes

Experience the allure of Salem Lakes Chalet, featuring modern comforts nestled within a quaint 3-story log cabin. Relax in a fenced yard offering picturesque vistas of woods, and relish in the variety of recreational options at nearby lakes. Your ideal retreat beckons! Enjoy the northern ambiance without the lengthy journey—be amazed by our expansive wall of windows! Whether you are in town to visit family or looking for a retrieve from the city we are conveniently located 10 mins from I-94.

Superhost

Tiny home in Beach Park

4.83 out of 5 average rating, 101 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

4.92 out of 5 average rating, 124 reviews

Home in Waukegan

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!

Superhost

Flat in Waukegan

4.82 out of 5 average rating, 135 reviews

Cozy Corner, stylish 1bed near Navy Base!

Kick back and relax in this calm, stylish space. This is a newly remodeled 1 bedroom apartment. The Cozy Corner is designed to be a place of peace, for rest and relaxation. Feel right at home in this beautiful apartment. The kitchen is stocked with plenty of utensils and cookware for your favorite meal. Be sure to relax by the indoor fireplace and watch your favorite movies. Dedicated work space with desk and fast wifi perfect for traveling professionals. Longer stays discounted!

4.94 out of 5 average rating, 18 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).

4.98 out of 5 average rating, 235 reviews

Flat in Kenosha

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!

4.76 out of 5 average rating, 364 reviews

Home in Kenosha

Lake Michigan Paradise Apartment

Private, top floor unit in a duplex on Lake Michigan w/ 900 square feet, 2 bedrooms, 1 large bathroom with shower and soaker tub, open concept living perfect for an amazing getaway. Unobstructed views of Lake Michigan. Relax on your enormous 500 square foot private deck overlooking the lake. Great for fishing. Backyard available for your furry family members. Beach is around the corner. Downtown is a 3 minute walk and has beautiful boutiques, shops, eateries, museums and more!

4.99 out of 5 average rating, 150 reviews

Home in Round Lake Beach

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!

5 out of 5 average rating, 26 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.

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Other great holiday rentals in Winthrop Harbor

Flat in Kenosha

4.73 out of 5 average rating, 40 reviews

Designer luxury loft in perfect downtown location

MariaRating, 5 stars5 days ago

Our stay was great! It aligned well with the description, the pictures and the reviews. A well appointed, digitally enabled modern space, a refreshing surprise in the heart of Kenosha.

4.64 out of 5 average rating, 36 reviews

Perfectly Cozy!

ManuelRating, 5 stars3 weeks ago

stayed at Sonja place for one night and loved the house it was perfect for my family, defenetly will stay again

Place to stay in Racine

4.86 out of 5 average rating, 720 reviews

Wisconsin Treehouse Getaway!

ArielRating, 5 stars1 week ago

Beautiful space and property. Had a great stay and made wonderful memories. Main thing I’d say to be aware of is it is connected to the hosts’ actual home so keep that in mind. While the space is private, it’s not isolated. You may interact or hear the hosts’ family along the way. It wasn’t a big deal for us, but something to think about if you’re not fond of or used to it. Overall, great stay and recommend!

4.98 out of 5 average rating, 133 reviews

Private room in Racine

Cozy In Caledonia

AlekseyRating, 5 stars2 weeks ago

Great place to stay, because everything you would want

4.78 out of 5 average rating, 192 reviews

Private room in Kenosha

Private Cozy Brm with Bathrm and nearby Lake View

SkyRating, 5 stars1 month ago

My wife and I visited the area for a concert for her birthday. The space was nice and quiet and was exactly what we needed. Carlton was quick to respond to our questions. Highly recommended.

5 out of 5 average rating, 7 reviews

Home in Kenosha

Little House by the BIG LAKE

BarbaraRating, 5 stars4 days ago

My son stayed at Ethan‘s home for a little over a week and loved every minute. It was walkable to the lake and him and my granddaughter were able to enjoy the home and the space was perfect. We wish we could’ve stayed longer, but of course Ethan was fully booked as he should be with such a wonderful home. He was super communicative and very flexible in getting my son in on short notice the same day. Thank you, Ethan for Your home and all of your help.

4.5 out of 5 average rating, 12 reviews

This one feels like Home

SmitaRating, 5 stars1 week ago

Betty's home was beautiful, warm, and cozy. She's a wonderful host, very accommodating. She has a binder of some places to eat, shop, and recreations. She came by to bring us donuts, but we missed her. I thought that was very sweet.