From Milwaukee, Wisconsin, there are plenty of destinations — from small villages to big cities — within driving distance perfect for couples who need one-on-one time to reconnect. After settling into your Milwaukee vacation rental, embark on a short road trip to take your sweetheart to the top of the Willis Tower in Chicago, or head to Indiana to fuel your creative side. Snuggle up in a rustic cabin in Oshkosh, or reserve a luxurious villa in Madison when planning your next weekend getaway. Consider these cities in Wisconsin, Illinois, and Indiana when planning your next trip with that special someone.

1. Madison, Wisconsin

Trade one big city for another when choosing Madison, The City of Four Lakes, as your vacation destination for your romantic weekend. The state capital is only an hour from Milwaukee, and a vacation rental in Madison puts you in close proximity to the Capitol building, where you can tour historic artifacts with your sweetheart. Enjoy a romantic lunch at Dotty Dumpling’s Dowry before shopping the Dane County Farmers’ Market for specialty gifts together. Spring, summer, and fall getaways are perfect for walks, hand-in-hand, down historic State Street that leads to the University of Wisconsin campus.

Find vacation rentals in Madison

2. Valparaiso, Indiana

Immerse yourself in the creative culture of Valparaiso after making the three-hour drive from Milwaukee with that special someone. Start your adventures with a tour of the vibrant art scene that includes the Porter County Museum and the Brauer Museum of Art Center for the Arts. Take in a show at the Chicago Street Theatre or a musical performance that warms your heart at the Memorial Opera House. Couples who enjoy outdoor excursions can walk the trails at Rogers-Lakewood Park or tour the blooming flowers at Taltree Arboretum and Gardens before heading back to their vacation rental to sit by the fire or relax on the balcony.

Find vacation rentals in Valparaiso

3. Chicago, Illinois

Chicago is a hotspot for couples and is home to many famous attractions and settings for a big proposal or a sweet photo op. Take your love for a ride on the Ferris Wheel at Navy Pier to ignite that spark or share a kiss on the sky deck of the Willis Tower. Take a romantic walk along Lake Michigan during the warmer months, or bundle up and hit the retail stores on the Magnificent Mile when those Chicago winds whip through the air. Couples who dub themselves as aspiring artists enjoy touring the Art Institute of Chicago, whereas the history buffs flock to the Field Museum of Natural History.

Find vacation rentals in Chicago

Find the perfect Milwaukee vacation rental on is the world's #1 vacation rental search engine with over 10 million properties!

4. Baraboo, Wisconsin

A romantic getaway in the warmer months puts you in the water park capital of the world when you choose Baraboo as your vacation destination. Located just two hours from Milwaukee, this action-packed city gives you and your loved one the opportunity to ride the slides at Kalahari Resort’s safari-themed water park or Noah’s Ark water park. Continue your water adventures when renting a boat from Mirror Lake Rentals to see rock formations and gorges of Wisconsin Dells. Spend some one-on-one time with your mate bird watching and hiking at the International Crane Foundation’s headquarters before retreating to your cozy vacation rental.

Find vacation rentals near Baraboo

5. Oshkosh, Wisconsin

When you want a lakefront vacation rental to reconnect with nature and your loved one, make Oshkosh your vacation destination. Enjoy each other’s company and the shining sun when heading out for a boat ride on Lake Winnebago with On the Loos Cruises. Take a romantic walk through the Paine Art Center and Gardens, or work up a sweat together hiking the Wiowash Trail. Surprise your airplane-obsessed better half when you book a tour of the Experimental Aircraft Association’s Aviation Museum. Before the weekend is over, enjoy some one-on-one time and cold beverages at Gardina’s Wine Bar and Cafe.

Find vacation rentals in Oshkosh

6. Kohler, Wisconsin

Opt for a small village to rekindle that spark with a vacation rental in Kohler, located an hour from downtown Milwaukee. Test each other’s athletic abilities with 18 holes of golf at the Whistling Straits Golf Course, or indulge your quest for knowledge with a historical tour of the Walderhaus Museum or the Kohler Design Center. When you time your romantic getaway for the spring, you can enjoy the Festival of Beer and Food, held in the city’s downtown area. Bring back something special for each other when shopping at the Shops at Woodlake Kohler.

Find vacation rentals near Kohler

7. Minocqua, Wisconsin

Immerse yourselves in nature when opting for a vacation rental in Minocqua, an area home to the Bearskin State Trail, located four hours from Milwaukee. Get a scenic view of the city from above with a ziplining excursion with Northwoods Zip Line, or show off your adventurous sides when taking flyboarding lessons with Wild Side Flyboarding. You and your sweetheart can also pet exotic animals at the Wildwood Wildlife Park or take a boat tour with Minocqua Pontoon Cruises. Top off your weekend adventures with an intimate dinner for two at The Boathouse or Smokey’s Fine Dining Restaurant.

Find vacation rentals in Minocqua

Ready to go? Check out these amazing Milwaukee vacation rentals on