Castanheiro Boutique Hotel, Funchal Set in the heart of Funchal’s atmospheric Old Town, the five historic houses that make up Castanheiro offer guests an immersion in more than 300 years of Madeiran history. Communal areas in each house are filled with antique furniture and period pieces from its earlier incarnations – one as a handcraft atelier, another the home of wealthy traders – while bedrooms are sleek and modern. The cherry on the cake is the rooftop pool, with fantastic views over Funchal and plenty of quiet outdoor spaces on the walled terraces for relaxing with a book or a cocktail. There’s no restaurant, but plenty of good options within a minute or two’s stroll. Doubles from £153 B&B; castanheiroboutiquehotel.com Socalco Nature, Calheta Created by one of Madeira’s best-known chefs, Octávio Freitas, Socalco offers guests the chance to immerse themselves in the island’s natural landscapes, gastronomy and wine, with cookery classes, wine-tours and things to do around the farm. There’s plenty of chance to relax, too, with an honesty bar, a freshwater pool and solarium overlooking the Atlantic and gardens planted with vegetables and aromatic herbs, crisscrossed with levadas (historic aqueducts developed into walking trails). Accommodation is either in individual houses, linked by limestone paths, or rooms in the main house, with superb views out to sea. Doubles from £133 B&B; socalconature.com Estalagem da Ponta do Sol Set on a clifftop above the small resort of Ponta do Sol, this chic design hotel is a clever conversion of a former quinta, reimagining the spaces in minimalist black and white, with floor-to-ceiling windows that flood the communal spaces with crisp, bright sunlight. A great choice for a restorative break; yoga and qigong sessions are included in the rate, along with indoor and outdoor pools, sauna and steam, with a wide choice of massages available (payable on site). Cocktail hour can be taken by the outdoor fire on the bar terrace, with Mediterranean dishes given a Madeiran twist and served in the Michelin guide-listed restaurant. Doubles from £92 B&B; pontadosol.com Quinta do Furão, Santana Explore Madeira’s spectacular north coast by basing yourself at this clifftop quinta, with widescreen sea views and five hectares of lushly planted grounds including a large swathe of vineyard. Bedrooms are crisp and unfussy, the wellness area boasts a good-sized pool and tempting menu of massages, and dinner in the charmingly rustic restaurant – whether on the terrace on warmer evenings, or by the fire if cold – offers the chance to try classic Madeiran dishes. Ideal for walkers, many of Madeira’s spectacular levadas are close by. Doubles from £180 B&B; quintadofurao.com Atrio, Calheta Billing itself as an island within an island, Atrio is a bucolically lovely escape, run by Emmanuelle and Mickael, who have created the type of hotel they always wanted to stay in. The vibe is relaxed retreat, with all the necessary comforts, including a Klafs sauna, heated pool and restaurant menu that includes a good range of veggie, GF and lactose-intolerant options. Beyond the hotel’s lush gardens, the Levada Nova da Calheta is just 10 minutes’ stroll – the starting point for several walks, with rental bikes available and whale-watching tours to book. Twenty of the 22 rooms come with lovely sea views, with most spread through the gardens, each with its own private terrace. Doubles from £78 B&B; atrio-madeira.com 1905 Zino’s Palace, Ponta do Sol It’s impossible to miss Zino’s – an eye-catching, bubblegum-pink mansion set above the quiet seaside town of Ponta do Sol, designed as a summer house for the Zino family at the turn of the 20th century. It’s one of the island’s most charming hotels, with rooms in dusky-pink or sage-green with art deco fittings and modernist touches, and a small pool – also pink – ideal for cooling off after a walk along the nearby levadas. Breakfast goes on till noon, with a snack menu on offer all day, while Ponta do Sol, offering a little more bustle, is ideal for dinner in the evenings. Doubles from £148 B&B; 1905zinospalace.com​ The Vine Hotel, Funchal Dark and light combine in Funchal’s leading design hotel, with a wine focus running through everything from the vinotherapy treatments in the Wine Therapy Spa to the floors, each representing a season in the life cycle of a grape. The purple and khaki hues give a modern-boudoir feel to the interiors, balanced out by the sundrenched rooftop, with a sizeable infinity pool and 20m hot tub, both with majestic views of Fort São João and the mountains beyond. Bedrooms are minimalist but super-comfortable and the Terra restaurant is one of the best in town. Doubles from £164 B&B; hotelthevine.com Solar da Bica, São Vicente Ideal for those looking to drop off-grid for a few days, this small, 11-room hotel is tucked away in the beautiful São Vicente valley, overlooked by forest-clad mountains latticed with walking trails. Bedrooms are functional and comfortable, and there’s an indoor pool and sauna for soothing aching feet after a day’s hiking. But really, this is all about the location. Outside, the charming garden is planted with vegetables, fruits and aromatic herbs, many of which find their way on to the breakfast table, and there are two outdoor terraces with lovely mountain views. A car is pretty much essential, with good restaurants just a short drive away. Doubles from £106 B&B; solardabica.pt Se Boutique Hotel, Funchal Just a few steps from the city’s imposing 15th-century cathedral, the Se combines sleek, all-white bedrooms with bold colours throughout the rest of the hotel – vibrant green in the restaurant, teal-blue on the roof terrace – complete with sunken lawn – and an eclectic mix of retro and antique furniture. Sunset drinks on the roof terrace, with 360-degree city views, are a must, as is dinner on the streetside terrace at O Calhau, where dishes are created with ingredients from the family’s organic farm in Camacha. The small indoor pool and menu of massage therapies are the perfect restorative treat after a day’s sightseeing around the city. Doubles from £139 B&B; seboutiquehotel.com Quinta Jardins do Lago An island institution, this is a great choice for garden lovers, and those wanting to experience the best of Madeira’s breed of classic country estate hotels. The elegant 18th-century quinta is set in 2.5 hectares of bloom-filled botanical gardens, with more than 500 different plant species and a number of some rare and very old trees. Interiors are classic, rather than contemporary, but rooms are light and airy. The Colombo bistro offers relaxing poolside lunches, and dinners at the Beresford restaurant feature traditional Madeiran dishes in considerable style.