Hotel is set in the market place in a very nice small town nestled inbetween a charity shop and chinese restaurant (Great food). The car parking is not easy to find and is not lit at night with no security it is a lightly gravelled pot holed area round behind the chinese (300yds). You have to park outside the hotel drop of your baggage then take your car around the back to park. We stayed over the weekend and were not disturbed much by the market being set up in the morning, unloading the car in a narrow one vehicle wide one way system was awkward
The stairs up to the rooms was carpeted but needed a good cleaning. Our room was a nice size the floor like the rest of the hotel had oldie worldie feel with creaky uneven floors. The clothes had to be hung outside the only wardrobe as it was broken. The carpet and furniture in the room as with most of the hotel was very tired and in serious need of some TLC. The bar /lounge open fire was smoking and the whole place smelt of wood smoke. The menu was sparse and because we were bb + evening meal it was explained that only certain items on the menu could be eaten without paying extra. As it was the wives birthday we went for the Rib eye steak, wrong choice, it was flat, tasting nothing like steak and could have been used as soles for our shoes, veg was extra ( salad). It was replaced by another meal (belly pork) when we complained without any problems by the very good natured and helpful staff..
The following day we ate out at the Chinese Good move. As I said in the title with some Tender Loving Care internally it could be a jem once again.

A lovely old hotel packed with charm, located in a fabulous town directly in the market place. We've stayed here many times, it's not the Ritz but is worth the stay, particularly in some of their top floor rooms. Friendly staff and helpful when we needed something. We look forward to staying there again.

Stay was over 2 days as part of a New Year package that included afternoon tea on the day of arrival and 2 nights dinner b & b with a DJ for NY eve. This is a 400 year old ex-coaching inn which has a tourist board 3 star rating. Some past reviewers equate this to the 'AA' style 3 star system which is not the same. The fabric of the historic building is fair for its age. It has wooden framed single glazed windows and plenty of character. Open fires, exposed beams, stone flagged floors all add to its charm. Some modern hotels are smarter with more 'mod cons' but tend to be somewhat 'soul-less'.
Food was good and the manager, Mr Singh was on site to check on his guests throughout. The wine list was expensive. The central heating in our room was the only cause for complaint insofar as it was flat out till 1a.m. and refused my attempts to turn it down. The room was also a little too dark which would be easily remedied by a standard lamp or similar.
Oakham and its surroundings (e.g. Stamford) is well worth a visit and the Whipper Inn, whilst needing some modest smartening up is a good a place as any to make a base.

Great cosy, small, charming accomodation that is situated in th centre of Oakham. The country food options are very tasty and reasonably priced, also.