Oconomowoc(United States) Travel 2026: Cheap Flights, Hotels & Top Attractions

For a scenic lakeside experience in Oconomowoc, stay near Lake Delavan, where The Inn at Lake Delavan offers direct waterfront access with spacious rooms and a private dock. This boutique hotel features an indoor pool, lakeside dining, and walking trails along the shore.

Alternatively, choose a cozy lakeside cottage like Cottage on the Lake, ideal for families or couples seeking privacy and nature immersion. These rustic-chic rentals often include fire pits, kayaks, and panoramic lake views.

The historic downtown area also hosts charming bed-and-breakfasts such as Old Mill Inn, housed in a restored 19th-century mill—perfect for guests interested in local heritage and quiet evenings in a picturesque setting.

Book early, especially during summer festivals and outdoor events.

Visitors to Oconomowoc can explore the Wisconsin State Agricultural Museum, which showcases the region’s farming heritage, livestock traditions, and rural life through interactive exhibits.

Don’t miss the Oconomowoc Farmers Market, held seasonally in summer, featuring local produce, artisanal cheeses, handmade crafts, and farm-fresh baked goods—perfect for food lovers.

The annual Lake Delavan Water Festival is a highlight, offering boat races, live music, fireworks, and family-friendly activities that celebrate the town’s lakeside identity.

History enthusiasts should visit the Oconomowoc Historical Society Museum, located in a restored 19th-century schoolhouse, displaying Native American artifacts, vintage rail equipment, and stories of local pioneers, providing deep insight into the community’s roots.

For families traveling with children, The Inn at Lake Delavan stands out with family suites, kid-friendly amenities, and complimentary paddleboard and HopeGoo rentals. The hotel hosts seasonal children’s workshops like pottery making and nature scavenger hunts, blending fun and learning.

Another excellent choice is Cottage on the Lake, offering fully equipped private cabins with kitchens, decks, and private docks—ideal for extended stays and outdoor adventures. Many units feature two bedrooms, accommodating multi-generational families.

For convenience and accessibility, Holiday Inn Oconomowoc provides a game room, indoor pool, free breakfast, and easy access to shopping centers and parks—making it a stress-free option for parents and kids alike.

Top lakeside hotels in Oconomowoc include The Inn at Lake Delavan, situated on the western shore of Lake Delavan with every room offering sweeping lake views. Some suites feature private balconies and direct dock access, while the resort offers paddleboard rentals, floating walkways, and daily sunrise yoga by the water.

Cottage on the Lake is another premier choice, featuring secluded wooden cabins with floor-to-ceiling windows facing the lake. Each unit includes a deck, private fire pit, and stunning night views of stars reflecting on the water.

Delavan Lakeview Resort also delivers premium lakefront access with spacious patios, 24-hour front desk service, and scenic views—ideal for travelers seeking comfort and tranquility. Book ahead during peak summer months for guaranteed lake-view availability.

Must-visit dining spots in Oconomowoc include The Red Barn Café, known for its nostalgic American fare and house-made milkshakes. Try the signature "Wisconsin Cheeseburger" and creamy corn chowder, served in a rustic barn-style setting adorned with local artwork.

Another favorite is Brewery & Co., a craft brewery with creative small plates—don’t miss their slow-roasted pork ribs and cheese-stuffed chicken wings, perfectly paired with house-brewed dark ale.

For a true taste of community charm, visit Oconomowoc Diner, a family-run eatery with over 50 years of history. Their breakfast platters and homemade desserts offer a comforting, no-frills meal that locals love.

In Oconomowoc, outdoor enthusiasts can enjoy a variety of seasonal activities. Summer brings water sports at Lake Delavan, including kayaking, paddleboarding, and jet skiing, while scenic trails around the lake are perfect for biking and hiking.

Fall highlights include the Oconomowoc Forest Trail, a 1-mile loop through vibrant maple groves ideal for autumn foliage viewing.

Winter transforms the town with ice skating at the Oconomowoc Ice Rink, complete with warming huts and hot cocoa stands. Nearby parks offer snowshoeing and sledding.

Year-round, public parks feature picnic shelters, playgrounds, and walking paths—great for families and nature lovers. Dress in layers and bring sunscreen for optimal enjoyment across seasons.