At the age of 24, Nicholas Crawley became a Director of Historic House Hotels Ltd. This Company, which was privately funded, opened three hotels in the UK:

• Bodysgallen Hall, North Wales
• Middlethorpe Hall, York
• Hartwell House, near Aylesbury

All three hotels are members of Relais Chateaux and won many plaudits in the guidebooks over the years. The Company obtained the Queen's Award for Export and a Prince of Wales Award for the restoration of Bodysgallen. Nicholas had responsibility for aspects of operating the hotels and a particular responsibility for converting the listed buildings (two of them Grade I) into hotels.

Nicholas Crawley was Managing Director of this group of hotels, which at its peak operated 130 hotels and over 20 restaurants in the UK. The group was the seventh largest hotel company in the UK in the late 1990s.

In 1998, the Company turned over £117 million making pre-tax profits of £20 million. During Nicholas Crawley’s tenure as Managing Director, the share price quadrupled in value. In 2000, the Company was taken over by Malaysian United Industries and eventually privatized.

Nicholas served eight years as Chairman of this award-winning five-star hotel in St Barths. The Hotel consistently won awards in Conde Nast as one of the best hotels in the world.

The Hotel had 40 rooms and suites and achieved an average room rate in 2015 of Euros 1,000 a night. The Hotel was sold in 2015 for what was estimated by CBRE to be a world record price per room.

In 2001, Nicholas Crawley helped convert the Old headquarters of the Scotsman Newspaper Group into a five-star hotel with 55 rooms, whisky bar, two restaurants, and a health club and spa. There was also a screening room and art gallery.

The Group also owned 42, The Calls in Leeds – a four-star boutique hotel with a Michelin starred restaurant. The Hotel de la Tremoille in Paris was purchased in 2002 and completely refurbished as a five-star 93-bedroom hotel with a small spa. The Hotel in the "Golden Triangle" of Paris remains one of the best hotels in Paris.

Nicholas Crawley was a Director of Four Pillars Hotels, which owned and operated six hotels in Oxford, the Cotswolds, and the Thames Valley. They operated in the three and four-star sectors, including two listed buildings – Tortworth Court and Oxford Thames. The Company obtained planning permission and built the 318-bedroom Cotswold Water Park Hotel.

The hotels were eventually all sold to Starwood Capital.

Nicholas Crawley was Managing Director of St James's Hotel Group until 2019, along with Simon Porter, who was Director of Estates.

The Company, via its parent company Somerston, acquired fourteen unbranded 3 Star Hotels from Forestdale Hotels, as well as the Hilton Hotel Portsmouth and the Legacy Falcon Hotel Stratford-Upon-Avon. Nicholas and Simon presided over the redevelopment of these hotel properties and the disposal of non-core assets.

2019 saw the completion of a multimillion-pound redevelopment of the hotels in Bath and Stratford. These hotels were expanded, significantly upgraded, and converted to 4-star IHG Hotel Indigos, complemented with outsourced food and beverage operated by a Michelin star chef.