Sam and Dean stop for drive-thru supper and Dean gets a call from a hunter, Annie Hawkins. She offers her condolences about Bobby and then tells Dean that she has some of Bobby's old books and suggests they meet at nearby Bodega Bay to hand them over.
Two teenagers, Debbie Tellen and Dudley Scott, are making out at a house. Annie pulls up outside and the teenagers quickly break it off and try to run out of the house, and see a man standing in the hallway. He says they shouldn't have come there and charges at them.
Annie enters the house and finds the two teenagers, their throats ripped out. Her flashlight flickers and the door closes behind her.
Sam and Dean wait at the Crow's Nest Inn and read up on Dick Roman's current activities funding archaeological digs. Dean finally calls Annie when she doesn't show, and Sam mentions that Annie had a thing with Bobby. The brothers realize that the two of them both had something with her at separate times as well. Annie doesn't pick up and Dean pours himself a drink from Bobby's flask, and admits that it's better that Bobby didn't come back as a ghost. As they talk, the flask shifts slightly on its own.
As the brothers go out to their car, Sam suggests that Dean put the flask away because it reminds them of Bobby, but Dean says that he's not ready. They're unaware that Bobby is in the back of their car as they go to Annie's hotel room. She has clippings on a series of disappearances of teenagers in the area near the Van Ness House, which on an America's Most Haunted Houses list. There were disappearances for years, and then they stopped until recently. While they talk, Bobby tries to move something so they know he's there, but finds it too exhausting in his current state. They finally leave, taking the flask with them, and Bobby goes with it.
At the Van Ness House, the brothers look around while Bobby realizes that he can see all of the ghosts that occupy the house. However, none of them respond to him. The ghost of the owner, Whitman Van Hess, tells the one that attacked the teenagers, Dexter O'Connell, that he shouldn't have done what he did and warns that if he does it again then there will be consequences. As the brothers pick up EM readings, Dean tries to call Annie and they hear her phone ringing down the hallway. They find it but no sign of Annie.
As Bobby looks around, Annie approaches him and is able to see him. He realizes that if she can see him then she's also a ghost. She explains that she never saw a reaper, and is shocked that Bobby deliberately ran away from his. He explains that he has unfinished business, and they see the ghosts of the two teenagers walk by. Annie talks about how Dexter came after her and then she died. Bobby explains that he doesn't seem to be able to do any poltergeist-type activities, and Annie warns that it's messed up.
Sam and Dean figure that there could be several vengeful spirits in the house, but find no traces of any murders. They check Annie's phone and find a ghostly message with no originating number.
One of the ghosts, Haskel Crane, enters the parlor where Annie and Bobby are sitting and adjusts a chair. When they try to get his attention, he ignores them and Bobby tries to move something again and fails. Haskel dismisses them as amateurs and informs them that he's been a ghost for 80 years. They compare notes and Haskel says that he was stabbed in the house in 1932. When Bobby asks who did it, Haskel refuses to answer and starts to leave. Annie appeals to Haskel's better nature and he suggests that she start small with a candlestick. Bobby and Annie both try without success and Haskel tells them that they have to let go of their frustrations and calmly tell the object what to do. When that doesn't work, Haskel tells him that his alternative is to unleash rage and tells Bobby that he's a pathetic excuse for a ghost. A female ghost suddenly screams and charges at Bobby, and then disappears. Haskel says that eventually all of them deteriorate until there's nothing left.
Dean and Sam come into the parlor and Annie tries to get their attention without success. As they leave, Annie wonders where her body is and notices a female ghost, Victoria Dodd, watching them. They talk to her and realize that it was her voice on Annie's phone. Victoria asks them to free her but before she can answer, Bobby suddenly disappears.
Outside the house, Dean drinks from Bobby's flask and Bobby's ghost reappears in their car. They find a flyer for the Bodega Bay Historical Society and talk to the manager, Quentin. Quentin tells them about the house while Bobby tries to move a lantern without success. Meanwhile, Quentin talks about the owner, Whitman Van Hess, who lost his fortune and let the house become a bordello. Dexter was a convict who Whitman hired as a groundskeeper, but Dexter killed Whitman's fiancée on the eve of her wedding. As the brothers start to leave, Quentin notes that Annie was there earlier and asked about the house, and he warned her to stay away from the house because it isn't safe.
Sam and Dean check into a motel and go over the old newspaper clippings. Dexter murdered several prostitutes who worked at the house, escaped, and then returned to the house and was shot to death. While Dean takes a shower, Bobby tries to calm himself.
Two of Debbie and Dudley's friends, Brian and Jesse, go to the house that night and film a video as a warning about their friends.
When Dean gets out of the shower, he discovers that the words "Annie trapped in house" are written in the steamed-up mirror. Dean calls Sam in and asks who is there, and the faucets turn on by themselves and the word "Bobby" appears on the mirror.
The two boys walk through the house and narrate their video. The door closes behind them.
Dean realizes that Bobby is there and they realize that he's attached to the flask. The brothers head back for the house.
Dexter appears in the hallway and charges at the two teenagers, insisting that they shouldn't have come there. When they try to run, Whitman appears and tells Dexter to stop. When the boys thank him, Whitman rips their hearts out while Annie watches from the shadows. Whitman complains that Dexter tried to warn them away and that Whitman has enough victims. When the convict tries to leave, Whitman destroys him in a burst of golden energy.
Once Whitman leaves, Annie goes to the bodies and tries to grab their camera. As Victoria appears, Annie realizes that she can't grab the camera and asks Victoria for help. Victoria refuses and explains that Whitman punished Dexter by draining him. She tells Annie that Whitman uses the ghosts in the house to amuse himself, and that he killed his fiancée and framed Dexter for the crime. Victoria worked there as a prostitute and Whitman slit her throat. She doesn't know where Whitman keeps the bodies, explaining that none of the ghosts dare follow him around. Annie vows to destroy him and tells Victoria to grab the camera, and she reluctantly does. They hear Whitman coming and duck out of the room as he comes back and drags the two bodies away. He opens a secret panel and goes inside.
Outside, Sam and Dean figure that something kept them from finding Annie's body. They load up and go inside, while Bobby follows them in. he manages to grab his flask from Dean's pocket and then moves off from the brothers. Meanwhile, the video camera drops in front of Dean and he picks it up. The Winchesters play the video back and they see Annie on the video.
Bobby is there with Annie and Victoria, and Annie asks Victoria to let the Winchesters know that they're there since she and Bobby can't. Victoria warns that it's too dangerous but Annie insists that the brothers can help. The ghost appears to them and explains that Bobby and Annie are there and they're all in danger from Whitman. Before Victoria can tell them more, Whitman drains the energy from her. As the brothers leave for the cemetery, they're unaware that Whitman has slipped his key into Sam's pocket. He's able to leave with them while Bobby and Annie watch helplessly.
Once the brothers leave, Bobby blames himself for removing the flask from Dean, but Annie says that they should take advantage of Whitman's absence to search the house. They go to Whitman's room and find a roaring fire, and realize that Whitman burned Victoria's corpse to destroy her spirit. Bobby has Annie go over the house's history and she mentions that it was a speakeasy, and Bobby figures that there's a hidden compartment let over from Prohibition. They find the secret panel and Bobby is able to move the triggering switch with his mind. Inside they find the corpses of Whitman's victims... including Annie's. She wonders what happens to ghosts once they move in and Bobby figures that they just go. Annie says that's what she wants and asks for a hunter's funeral because she's ready for some peace. She tells Bobby that all she had was work. Bobby insists that he's not done yet, but Annie says that she is and asks him to do it for her.
Sam and Dean drive to the cemetery and find the Van Ness mausoleum. The car suddenly accelerates on its own and they realize that the ghost is responsible. Whitman appears and wrestles for control of the car, and Dean manages to stop it just in time. The brothers get out and figure that there's something on them. Sam finds the key but Whitman attacks him. Dean shoots the key and Whitman is "snapped" back to the house.
Dean and Annie prepare a fire to burn the bones of Whitman's victims. He enters the room seconds later and then realizes that they've gone downstairs. Whitman goes after them and grabs Bobby, draining his energy. However, at the cemetery the Winchesters burn his bones and Whitman's ghost disappears as Bobby collapses to the floor. Annie goes to him and makes sure that he's okay.
Bobby wakes up a few hours later and Annie confirms that he's okay. Sam and Dean come in and Bobby realizes that they can see him. Bobby tells them that Annie is there and they ask how he stayed there. Bobby gives them the flask back and Sam realizes that he never got a response because he was never near the flask when he tried to contact Bobby's spirit. Bobby says that he stayed because he needed to help them and leads them to the bodies of Whitman's victims.
Once they get done burning the bones, including Annie's, Bobby admits that he'll miss her. They share a toast in her honor and then Dean demands to know what Bobby was thinking, staying on Earth rather than going on to Heaven. Bobby insists that they have work to do and it's important, but Dean says that it's not right. Disgusted, Bobby disappears. As they drive off, the brothers wonder what they should do. Dean says that what Bobby's doing isn't part of the natural order of things and he doesn't think it will end well. In the back, Bobby listens to them, silent and unobserved.