The two properties bought in an off-market deal worth more than £5m take the company's estate to 10 and form part of its £20m expansion programme.
Founder and managing director, Kevin Charity, said: “Awareness of our acquisition plans is enabling us to have a number of off-market meetings in the coaching inns sector. This deal was the result of one of those discussions and fits perfectly with our expansion plans.
“The Golden Fleece is a famous coaching inn, steeped in history, whilst The Feathers is an extremely popular traditional inn in the busy market town of Helmsley, both at the gateway to the beautiful North Yorkshire Moors."
Charity said Coaching Inns Group would continue to work with the 'existing, highly successful management teams' at each of the new venues and would invest in both sites in the New Year.
"We’ll be investing across accommodation, food and beverage, and adding to what is already a very well supported offering," he said.
The Bulldog Hotel Group re-branded as Coaching Inns Group in August as part of plans to become a leader in the sector.
“Our aim is to be the number one operator of regional inns in the country and the name change is the natural next step for us, giving the market a very clear signal as to our sector leadership ambitions," said Charity.
The Coaching Inn Group operates individually styled coaching inns, each with an all-day offer, across the UK and has built a strong reputation in the industry for transforming underperforming establishments into busy and profitable businesses.
Property search firm PH Land and Developments acted as agents on the transaction for the Coaching Inn Group.