Hit The Road
Ready to plan a little getaway? This month we’re exploring ways to make your vacation home dreams a reality, checking out some of the best small towns in the Midwest, and discovering ways to invest in your future.
Choose Your Adventure
Ready to dive into the world of vacation home ownership? One of the first steps towards finding the right property is deciding on the type of second home you’d like to own. There’s a home match out there for everyone, you just need to decide on your vibe!
Ready for a rugged getaway?
A secluded cabin or mountain haven might be just what you need. Surround yourself with the beauty of the great outdoors and unwind! If you’re seeking a retreat from the hustle and bustle of city living, then a wooded wonderland can offer an escape from the daily grind. If winter sports are more your speed, a mountainside retreat will provide plenty of views and access to the slopes all winter long.
Looking for a waterfront locale?
Are you longing for lake living or an ocean escape? From the picturesque beauty of rolling waves and sandy beaches of coastal towns to the serene beauty of sleepy inlets, beach- and lakeside properties are in high demand. With a variety of watersports, warm weather activities, and bountiful natural views available, a waterfront home is perfect for anyone seeking an active outdoor scene.
Thinking outside the box?
A vacation home doesn’t have to be in a far-off location. If you’re craving nightlife or a booming arts and dining scene, your perfect vacation home may be in or near a more densely populated town. A townhome or condo near your favorite hot spots will offer streamlined living spaces without the fuss of big maintenance responsibilities.
Make the Most of Your Investment
A vacation home offers the possibility of rental income, in addition to being a private oasis for you and your family. If you’ve considered buying a second home that can double as a short-term vacation rental property, here are a few things to keep in mind.
- Do the math. You’ll need to analyze what it will cost you to rent your home versus the income you can expect to generate. Renting out your second home comes with some additional expenses, like maintenance, licensing, and repairs. If you desire the flexibility to visit your home throughout the year, you’ll need to determine how many weeks of short-term vacation rentals you’ll offer, and account for possible vacancies and cleaning costs between renters.
- Determine who will manage the rental process. Managing a rental property yourself offers a greater financial return, but it requires more work. Companies like HomeAway, VRBO, and Airbnb offer full-service booking systems—from finding renters to communication to payment processing—which can make the rental booking process easier for a small fee. You’ll also want to hire and oversee cleaning and maintenance professionals that can take care of the property between renters.
- Mind the details. From professional photography to a well-appointed space, the details matter when renting out your vacation home. Typical guests expect most of what they would get if staying at a hotel, like fast wi-fi, an expansive cable package, and other entertainment options. Having toiletries and basic cleaning supplies on hand are also a nice touch that will help your rental stand out. When advertising your rental, high quality photos and a detailed description will help potential guests decide if your listing is right for them.
- Make sure you’re covered. A dependable cleaning and maintenance crew is imperative to a successful vacation rental. If you don’t live nearby, or don’t intend to take care of cleaning and repairs yourself, having a trusted group of vendors to be your eyes and ears on the ground will help the rental process run smoothly. You’ll also want to check your homeowner’s insurance policy, as they rarely cover a vacation rental. In that case, you’ll want to secure the right type of policy to cover your investment.
- Comply with regulations. Depending on the location of your vacation home, you may be required to register your property or get a business license. Many municipalities will also collect a hospitality tax, like those collected from hotels, from owners of vacation rentals. You can handle this yourself, or hire a service to help keep you tax compliant. You’ll also need to ensure you can legally rent your home, so confirm with your homeowner’s association and local government that short-term rentals are allowed.
- Prepare yourself for guests. Make rules and build a strong rental agreement, so that guests are clear on what is permitted on site. Decide the max number of guests allowed per stay, whether pets are welcome, or if smoking is acceptable. You’ll also want to be ready to screen prospective tenants, and be prepared to respond quickly to questions.
When you’re ready to road trip, these Midwestern destinations offer small town charm to help you recharge.
South Bend, IN | 90 miles/~1.5 hours
With access to amazing shopping and dining around the University of Notre Dame, and water sports along the St. Joseph River, you’ll never want to leave.
Oregon, IL | 100 miles/<2 hours
A tranquil town along the banks of the Rock River, Oregon is a nature-lover’s oasis with, rolling hills, rocky bluffs, and nearby Castle Rock State Park.
Cedarburg, WI | 112 miles/<2 hours
With a Main Street on the National Register of Historic Places, this quaint location is perfect for history buffs and tourists alike.
Nappanee, IN | 110 miles/~2 hours
Located in the heart of Amish Country, you’ll find delicious homemade treats and a relaxed lifestyle suited to unwinding.
Mt. Carroll, IL | 137 miles/<2.5 hours
Known for historic sites, this sleepy town offers lakeside entertainment, and one of the oldest summer theaters in the state—the Timber Lake Playhouse.
Madison, WI | 147 miles/<2.5 hours
Equal parts small town and bustling metropolis, Madison offers fine dining, outdoor activities, and lakefront living.
Galena, IL | 163 miles/<3 hours
Ride the free trolley to go restaurant-hopping down Main Street, kayak down the Galena River, or check out the views along the Galena River Trail.
Alton, IL | 286 miles/<4.5 hours
The birthplace of Miles Davis, this town is home to the Great River Road, known as one of the most scenic drives in the Midwest.