This brilliant holiday sees you jetting off to Madeira’s 4‑star Pestana Churchill Bay. You’ll feel right at home here.

Pestana has done it again! Another brand‑new Portuguese hotel is coming your way, and how would you like to be one of the first through the front doors? Pestana Churchill Bay is a four‑star property overlooking Madeira’s Câmara de Lobos and, like its namesake suggests, is inspired by Winston Churchill’s 12‑day visit to Madeira during World War II. The picturesque setting of this Portuguese gem sparked the former Prime Minister to set up his easel in the village ‑ and the paintings he created have been beautifully reflected in the accommodation décor at Pestana Churchill Bay. But, that’s not all. The hotel has a panoramic rooftop pool, a restaurant serving the best in local cuisine, and even a sauna for those days you just need to detox. Have we convinced you yet?

Why we love it
A delectable on‑site restaurant serving authentic Portuguese fare
A panoramic rooftop pool overlooking the stunning Câmara de Lobos
Spacious accommodation with décor inspired by the paintings of Winston Churchill

Famous for its luxurious resorts, beach holidays and fortified wine, Madeira is a multifaceted destination that opens up more and more as you venture further into the island. The capital of Funchal is a good place to start your Portuguese exploration. The squares and streets of the centre are dotted with tiles in endearing patterns, and quaint buildings aplenty. Interspersed among the shops and cafés are stunning cathedrals and churches, as well as numerous museums and monuments (including one by the harbour dedicated to footballer Cristiano Ronaldo).

Explore the narrow streets and alleyways of the Old Town, stroll along the palm‑lined promenade by the sea, gaze at the impressive cathedral and indulge in a bit of art and culture in the local museums. Take the cable car to the tiny hilltop village of Monte, just behind Funchal, for a truly stunning view of the capital and the landscape draped against the dark‑blue Atlantic background.

Your Holiday Starts Here

  • Feefo Trusted
  • Spread the Cost
  • £49pp Deposits
  • ABTA & ATOL