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Windamere is situated on historic Observatory Hill where Darjeeling began, and overlooks the Chowrasta, the town's exclusive promenade. From Observatory Hill, one can glimpse Tibet, Bhutan, Nepal and Sikkim, against a stupendous backdrop of twenty of the highest mountain peaks in the world.

It is "One of the three Jewels of the Raj", said a celebrated travel writer of The Windamere Hotel. Established in the 19th century as a cozy boarding house for bachelor English and Scottish tea planters, it was converted into a hotel just before the outbreak of the Second World War.

Well known to sophisticated travelers the world over, the Windamere is famous for its unique ambience and charm, and has been the subject of many leading stories in the international media. The Windamere wing appeals to guests who like tradition, who would be comfortable in a bygone age, and who want a reminder of how people got on with their lives in old Darjeeling.

There are no TVs and telephones in the main house called Ada Villa; and only telephones, by request, in the Annex. Guests, who choose this wing, prefer to avoid the distractions of modern life for the duration of their stay. Generations of newly-wedded couples have enjoyed the quiet ease afforded by Tinker Belle's Cottage (also known as Honeymoon Cottage).

The cottage is set apart from the rest of the hotel, on a sunny little spur that rises just above Windamere's Ada Villa. Couples return to the cottage for anniversaries, to snuggle before the fire in the evenings, only to remember and to dream of days long ago. The Snuggery wing appeals to people who need to remain in touch with modern life, even while they indulge their love of the past and old things.

The residential houses in this wing, Annandale House, and Observatory House, are provided with TVs and telephones. The bathrooms have fittings which were once the property of the Loreto Convent Girls School. These were donated to Windamere Hotel when the Convent   closed   down its boarding school after 130 memorable years.

The Convent is the oldest European school in Darjeeling District, having been founded in 1846.

It counts among its many famous former pupils, Vivien Leigh, the actress of "Gone with the Wind" fame.