Tucked away in the Midwest, Wisconsin is off the beaten track when it comes to romantic weekend getaway destinations. However, there are numerous incredible Wisconsin vacation rentals situated in quaint towns and villages that exude charm and romance. The fantastic state of Wisconsin is all about relaxing with a view and reconnecting with nature, so you can enjoy a stay at a waterfront cabin, and look forward to exploring sandstone formations, farms, and forests. Check out the most noteworthy cities and towns in Wisconsin ideal for a romantic weekend getaway.
Centrally located between Milwaukee and Madison, this southeastern Lake County town has a vibrant and modern downtown dressed in Williamsburg-era style. Outdoor enthusiasts find some of the state’s best trails in the Kettle Moraine State Forest and the Naga-Waukee County Park. You can fish, boat, or swim at Lake Nagawicka or try hitting a hole-in-one at Erin Hills, site of the 2017 U.S. Open. Delafield hosts the Wisconsin State Fair, a food and musical festival, and you can meet up with locals at the Delafield Block Party. Dine over festive fusion fare at Fishbone’s Cajun and Creole restaurant.
Bayfield gives you a well-earned escape from the hassle of day-to-day responsibilities. Two hours east of Duluth, Bayfield, on the sun-kissed shores of Lake Superior, is the gateway to the Apostle Island National Lakeshore in northern Wisconsin. This beautiful area is a cluster of wooded, gem-like islands and has 12 miles of mainland wilderness. You can take a boat tour for magnificent views of sandstone cliffs and sandy beaches or explore sea caves in winter or summer. Stop by the Candy Shoppe for fresh-dipped caramel apples. The Landmark Restaurant at Old Rittenhouse Inn is a wonderfully romantic place to share comfort food and excellent wine.
3. Sturgeon Bay
A shipbuilding hub, this circa 1835 waterfront village has captivating, small-town charm. You can find winter fun at the snow-carving competition held during the Fire and Ice Festival, or try some in-town Nordic skiing on five miles of groomed trails at Crossroads at Big Creek. Attend the annual fine arts festival in May, or search through the art and textile treasures at the citywide sidewalk sale in July. Hiking, biking, and picnic spots are plentiful at two state parks, and you can pick up some local history at the maritime museum. For an exquisitely romantic dinner, take your sweetheart to Donny’s Glidden Lodge or Trattoria Dal Santo.
Sparta is nestled in the green rolling hills of western Wisconsin, and from 1865 through 1880, it was known as Saratoga of the West due to the healing powers of local artesian springs. Sparta converted the first rail bed to bike trails and today claims bragging rights as the bicycling capital of America. The Lacrosse River Trail gives bikers a chance to take in beautiful scenery on a flat, easy-to-maneuver terrain with plenty of rest stops. You may steal a kiss or two as you wheel your bikes through the three-quarter-mile railroad tunnel that is well-kept but rather dark. Relax on a quaint outdoor patio and courtyard while tasting a selection of wines, beers, and ciders at Lost Island Wines. The Club Oasis is a romantic old-fashioned supper club, or you can celebrate your union with a ‘Thank Cod It’s Friday’ fish fry at Jake’s Northwoods Restaurant.
5. Lake Geneva
Experience the World Famous Mailboat Tour on the Lake Geneva Cruise Line. You not only observe beautiful estates and natural scenery from the water, but you can see the only marine mail service in action. Watch as a mail person leaps from the boat onto the pier, places the mail in the box, and springs back into the boat – a boat that never slows down while this feat is in progress. You can walk hand-in-hand along the gorgeous Geneva Lake shore path, or swim, kayak, and hike at the Big Foot Beach State Park. Spend quality time over a superb dinner at the romantic, Victorian-style Baker House or the Geneva Chop House.
This former flour and feed mill village has quaint brick buildings reminiscent of days gone by. The Cambridge Winery is a great place to sip and sample local wines; consider choosing a few bottles to take home and share with friends. There are plenty of cozy rentals around Lake Ripley, many with boat landings so you can laze along the river in privacy. Fish, hike, or explore the three natural areas that surround Cambridge. Enjoy a slow-smoked prime rib or juicy pork roast at the Plow, a converted 1848 feed mill that remains the last functioning ranch with livestock in the area.
This lovely town is on the Milwaukee River, and there are plenty of natural habitats to explore in the woodlands and along the hiking and biking trails. Take a tour of the Cedar Creek Winery, where you can find some white wine varieties that are unusual for the Midwest, then enjoy some tastings and wine pairings at the on-site restaurant. Don’t miss a photo op at the last covered bridge in the state. Pick a quiet spot by the babbling creek and share a picnic lunch. The General Store Museum is a kick. The 150-year-old frame building has a soda fountain, a variety of antique advertising art, and a checkerboard waiting for players as it rests on a barrel. Dine in the casual and rustic Anvil Pub and Grille located in an authentic, restored 19th-century blacksmith’s shop.
8. Sister Bay
This historic Door County village is a mecca of summer fun, from park concerts and professional musicals performed at the outdoor amphitheater in Peninsula State Park to swimming at the local watering holes. Explore this scenic park as you bike over hard-packed gravel paths that have numerous scenic overlooks. Sister Bay is known as a festival village, and you can have a blast at the annual Goat Parade. The Labor Day Marine Fest has terrific boat races, live entertainment, and a huge book sale. Enjoy authentic Swedish fare at Al Johnson’s, or have a tender, juicy steak on the rooftop at CHOP.
Ready to go? Check out these amazing Wisconsin vacation rentals on Tripping.com.