Discover small-town charm and scenic beauty with Darlington Vacation Rentals By Owner! Tucked in the rolling hills of southwest Wisconsin, Darlington offers cozy cottages, family homes, and peaceful country retreats—all with direct booking and no service fees. Enjoy the Pecatonica River Trail, historic downtown, and year-round events that celebrate the area’s heritage. Whether you're biking, fishing, or exploring the beautiful countryside, Darlington provides a quiet escape with a warm, welcoming feel. Our owner-managed rentals deliver comfort, privacy, and a personal touch. Book your Darlington getaway today and enjoy the slower pace and natural beauty of Wisconsin’s Driftless Region.