Lakefront Getaways & Second Homes: A Blend of Proximity and Paradise

As Chicagoans, we love our city! It’s vibrant, exciting, and always has something new to offer. But sometimes we all could benefit from a getaway destination — and what if, just like owning a home or investment property here in Chi, you could put a property to work for you?

That’s where second homes come in. A vacation home can be a place to relax and unwind, to explore new hobbies and interests, and — if done right — to act as an investment opportunity! Lucky for us, there’s plenty of amazing second home locations to choose from just a short drive away.

In this post, we’ll explore some of the most popular vacation home locations, all of which our Two Door Group team and extended, local partners can help you purchase. 

Through our coast-to-coast referral program, we can refer you to an agent that we trust, and who we know will find the perfect second home that embodies all of the charming attributes you’re looking for. 

And if you’re looking for somewhere a little further away (and warm all year round), let us introduce you to our Satori high end villas and condos in Tulum, Mexico, which are perfect for vacation rental income year round. Read on for plenty of #vacationvibes inspiration!

Top-Rated Second Home Locations in Michigan

New Buffalo: A Coastal Haven

Ahhh there’s nothing more “Pure Michigan” than the cozy, aquatic town of New Buffalo. Nestled along the shores of Lake Michigan, New Buffalo is a serene coastal town that provides an idyllic getaway for Chicagoans seeking a peaceful, aquatic lifestyle. Its close proximity to the city allows for quick and convenient escapes, while offering a wide variety of recreational activities such as boating, beach combing, and waterfront dining.

Grand Beach: Secluded Bliss

Seeking somewhere a little more secluded and beachy? Grand Beach could be your spot. Only a 10 minute drive from New Buffalo, Grand Beach provides a more private haven for those needing a break from the hustle and bustle of the city. This charming village exudes a welcoming atmosphere and offers a variety of outdoor activities, such as golfing, hiking, and biking. For avid golfers, Grand Beach boasts a renowned golf course that offers stunning lake views and challenging holes.

South Haven: Endless Delights

If you head a bit further north up the border of Lake Michigan, you’ll find yourself in gorgeous South Haven, a picturesque town that attracts many Chicagoans with its stunning views of the sunset, beautiful sandy beaches, and bustling downtown scene. From award-winning wineries to the vibrant blend of flavors at eclectic eateries, South Haven exudes a special charm that captivates all who visit. Owning a second home in this coastal paradise is sure to create memories that will last a lifetime, and could also attract renters if you’re looking to cleverly offset some of the costs of second home ownership. 

If you’re game to travel to a tropical escape that’s just a short plane ride away, we highly recommend the magical hideaway of Tulum, Mexico.  Here, Two Door Group co-founder Jen Vest is representing the builder/developer team of Satori – a stunning community of villas and condos set in the jungles and sandy beaches of Tulum. 

Your next home-away-from home is the perfect place to relax and unwind, or to explore the rich history and culture of the region. From the vibrant culture and local flavors to crystal-clear turquoise waters and the ancient Mayan ruins, there’s something for everyone at Satori.

The resort offers luxurious condos and villas, with seriously unparalleled amenities. So whether you’re looking for a vacation home or an investment property, Satori is the perfect place for you.

The cherry on top? Two Door Group proudly represents Satori and can help you find the perfect condo or villa for your needs. So what are you waiting for? Contact Two Door Group today and start planning your escape to Satori, Tulum!

Compass Connections Coast-to-Coast

Map of Compass markets coast to coast
Beyond the enchanting locations lake destinations of the Midwest, Two Door Group extends its expertise and reach across the country with Compass listings in prime destinations nationwide. With a strong network of real estate professionals and access to exclusive properties, we can assist you in finding your dream second home or investment property in numerous sought-after locations.

Let's Connect!

For more information, reach Two Door Group Co-Founders Adele Lang & Jen Vest at, or hit the Contact Us button up top!