I grew up in Oakham! Moved away in 2002 to go to uni. Moved back and forth since, but settled in Manchester now. My parents still live there. Lovely place, very much a small town attitude at night though. the Grainstore pub next door to the railway brews it’s own beer. You have rutland cycles in Whitwell (I used to work in there), and the tourist office in the car park in empingham, where I also used to work. On and the Sunken church museum, I used to work in there too;). Accommodation wise, I don’t think there is anything bad in the town and the surrounding villages, as it is quite an affluent area. So go with whats already been said.
Email is in the profile if you need any advice about the area.