Apartment holiday rentals in Lake Michigan

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Quiet Grand Mere Coach House on Lake Michigan

The Coach House is in an eclectic neighborhood on Lake Michigan. Grand Mere State Park is a year around beautiful place for hiking by small lakes and through beautiful sand dunes. A small beach is a 2 minute walk away. The family room and kitchen face Lake Michigan with lots of windows. The house has a queen bedroom, queen pullout in family room, and laundry. A gas FIRE PIT and a HOT TUB are located on the back patio directly on Lake Michigan with a spectacular view behind the main house.

Heart of Historical Dist.*King*Parking*A/C*#1

Our charming one bdrm (king)apt. is perfect for a getaway in NW IN; provides everything you need to have an enjoyable stay! *Check out other units in same building*. Located near Lighthouse Outlets, Restaurants, Casino, Breweries, Indiana Dunes Natl & State Parks (7 -11.3 miles), Washington Park (1.4 miles) and more! South Shore train platform is behind property(in quiet zone). Day trips are easy to downtown Chicago or South Bend IN. Catch a Notre Dame game one day and see the Bears the next.

Ukrainian Village Garden Retreat

A newly updated 1 bedroom, 1 bathroom apartment in Chicago's historic Ukrainian Village. Located a few blocks from Wicker Park, Ukrainian Village is a small historic district of Chicago filled with historic architecture. Access the apartment via a smart lock, the apartment includes everything you need for a comfortable stay, including a queen-sized bed, full kitchen, fiber high-speed internet (100+ Gbps up and down), smart TV, modern bathroom, in-unit washer & dryer, and free garage parking.

Cozy Vintage Studio for One Person

Studio for one non-smoker. Our usual guest is a busy academic, intern, medical worker or other professional. Located on the second floor of an old 4-unit apartment house, so there is some in-house sound transfer. Our neighborhood is usually quiet, but not always. See the LOCATION section under the map to check if our neighborhood is suitable for you. No smoking indoors or out. Memorial Hospital 3 blocks, Notre Dame 2.5 miles, downtown 1/2 mile. 8 minutes to SB Airport and 80/90 Toll Road.

Cute, Clean, Cozy Apartment in Pilsen

Updated, clean and private apartment in Chicago’s unique Pilsen neighborhood. Located on a quiet, tree-lined street with private entrance, it's the perfect spot to rest after a day of exploring this great neighborhood and city. The apartment has a full kitchen with everything needed to make your morning coffee or prepare a meal. Conveniently located to McCormick Place and many of the city's attractions, including West Loop, downtown, United Center, Grant / Union / Douglass Park and more!

Bright Cozy Modern-Chic Condo in Trendy West Town

Kick back & relax in your home away from home in our luxurious, spacious and peaceful abode in the heart of the West Town & Noble Square neighborhoods, close to downtown. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located near the popular Grand Avenue, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Sophisticated Flat in Historic Building

Nestled in the charming Old Town Triangle of Chicago, this luxurious flat offers a seamless blend of historic charm and contemporary sophistication. With its soaring ceilings and elegant arched windows, this immaculate space boasts a truly captivating ambiance. Impeccably designed interiors ensure a truly indulgent stay, while the building's rich heritage adds an unforgettable sense of place. Treat yourself to the ultimate Chicago getaway and bask in the allure of this stunning residence.

Private Entrance Guest Suite on the River

Stay in our studio apartment suite with private exterior door entrance. Hosts live in the rest of the house. From the backyard you can fish, kayak/canoe, paddle board, enjoy a bonfire, grill, and relax by the river. There's a king memory foam bed, sleeper sofa, and 49" TV. Remote work friendly with spacious workspace desk, fast WIFI, and coffee. The closet has a mini food prep area with mini fridge and microwave, and grill out on back patio. It's a quick 15 min drive to Notre Dame.

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

Cozy guest studio, great for couples!

This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

Modern Historic Firehouse in TC

Firehouse One was the first Fire Station to operate in the city way back in 1891. This stylish ground level flat at Firehouse One was built in 2022. It has one bedroom and one bathroom. It can accommodate up to 4 guests with free parking and fiber internet on-site. The space embraces the history and architecture of the building with its large windows, 10’ ceilings and exposed brick while introducing clean and modern furnishings for a comfortable atmosphere.