Where memories are made

About our homes

Welcome to Midwest Traveling!

We are so happy that you found us and we look forward to hosting you at one of our beautiful vacation homes across the Midwest.

Years ago we embarked on a real estate adventure, which has led us to form a new passion for interior design and hospitality.  Our short term rentals are designed with a fun twist or theme and include all the comforts of a fully furnished home.

ANDERSONVILLE - CHICAGO, IL
FUN & FUNKY ANDERSONVILLE RETREAT

Our unique three bedroom, two bathroom apartment in Andersonville - Chicago, IL is steps away from the historic Clark Street and is in one of Chicago's most eclectic neighborhoods. It is known for its Swedish roots as well as being home to one of the city's largest LGBTQ+ communities.

MICHIGAN CITY, IN
INDUNESRNR

Enjoy our spacious four bedroom, three bathroom duplex within a 10 minute walk to the south shore of Lake Michigan. This area is the tourist hub for the Indiana Dunes territory and also includes breweries, wineries, gardens, shopping, a casino and even a zoo!

NEW LISBON, WI
LA NOSTRA CASA & YEEHAW CABIN

Our nature-saturated, 3,000 sq ft homes in New Lisbon, WI (28 miles from The Wisconsin Dells) are located right next door to one another. Nestled in a small, secluded neighborhood, these homes can be rented together (sleep 29 total) or separately. They both have their own private beach set on a five acre, spring fed, catch and release lake.

Our Vision

We are driven by dedication to design unique homes that our guests can admire and create memorable experiences within. 

We go above and beyond to offer personalized service, insider recommendations, and warm and attentive hospitality.

Introducing

Our Host

midwest

Jacqueline DiMaggio

Owner/Manager

Frequently Asked Home Rental Questions

At Midwest Traveling, our booking conditions are designed to provide flexibility and convenience for our guests. We offer both online booking through our website and the option to contact our customer service team for assistance. To secure your reservation, we require a deposit or full payment, depending on the specific property and booking terms. Our rates are transparent and include all applicable taxes and fees. 

We understand that plans can change, and we strive to accommodate our guests’ needs. Our cancellation policy may vary depending on the specific property and booking terms. We recommend reviewing the cancellation policy stated at the time of booking or contacting our customer service team for further assistance. In some cases, we offer flexible cancellation options and the possibility of rescheduling your stay for a future date. Our goal is to provide fair and reasonable solutions to ensure your satisfaction.

We understand that pets are a part of the family, and we strive to accommodate their presence. However, we have a strict no pet policy. We only allow service animals and an additional $150 cleaning fee will be added to your stay.

Absolutely! We welcome families and strive to provide a child-friendly environment. Many of our vacation homes are suitable for children, with features such as spacious living areas, comfortable bedrooms, and amenities that cater to families. We aim to create a memorable and enjoyable experience for guests of all ages, ensuring that families feel right at home during their stay.

Depending on the property check-in time is typically in the afternoon, around 3:00 PM or 4:00 PM. As for check-out, it is usually in the morning, around 10:00 AM or 11:00 AM, to allow sufficient time for cleaning and preparation for the next guests. If you have specific requirements or need to arrange alternative times, please contact us, and we will do our best to accommodate your request.

  • Linens (bed sheets, pillows & blankets)
  • Bath towels, wash cloths, make-up towels & hand towels
  • Beach towels (blue and white striped)
  • Shampoo, Conditioner, Body wash
  • Fully equipped kitchen (spices, oils, pans, cutlery, etc)
  • Heating and cooling
  • Laundry soap
  • Dishwasher pods
  • Garbage bags
  • Dish Soap
  • First Aid Kit
  • Pack N’ Play
  • Firewood (WI homes)
  • Propane (fire pits & grills)
  • Paper towels (2 per kitchen sink/wet bar area)
  • Toilet paper (3 rolls per bathroom)
  • Smart TVs (please bring your own Log ins & Passwords) 
  • Personal Items
    Toiletries, sunscreen, insect repellent, medications, swimwear & all of your Smart TV log-ins & passwords
  • Kitchen Supplies
    Groceries and ingredients for cooking (depending on your meal plans) Reusable water bottles to stay hydrated during your adventures Snacks and beverages for on-the-go enjoyment
  • Beach/Lake Essentials
    Beach chairs, beach umbrella, beach blankets, beach toys, floaties/rafts, bicycles, ice skates & sleds

Are you Ready to book with us?

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