Castanheiro Boutique Hotel, Funchal
Located 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 Madeira history. The common areas in each house are filled with antique furniture and period pieces from its earlier incarnations – one as a handicraft atelier, another as the home of wealthy traders – while bedrooms are sleek and modern. The cherry on the cake is the rooftop swimming pool, with great views over Funchal and plenty of quiet outdoor spaces on the walled terraces for relaxing with a book or a cocktail. No restaurant, but plenty of good options within a minute or two.
Doubles from £153 B&B; castaanheirobutiquehotel.com
Nature Socalco, Calheta
Created by one of Madeira’s most famous chefs, Octávio Freitas, Socalco offers guests the opportunity to immerse themselves in the island’s natural landscapes, gastronomy and wine, with cooking classes, wine tours and things to do around the farm. There is also plenty of opportunity to relax, with an honesty bar, a freshwater swimming pool and a solarium overlooking the Atlantic and gardens planted with aromatic vegetables and herbs, crisscrossed with levadas (historic waterways developed into walking paths). Accommodation is in individual houses, connected by limestone walkways, or rooms in the main house, with stunning views out to sea.
Doubles from £133 B&B; socalconature.com
Estalagem da Ponta do Sol
Perched on a cliff above the small resort of Ponta do Sol, this chic design hotel is a smart conversion of a former quinta, reimagining the spaces in minimal black and white, with floor-to-ceiling windows that flood the communal spaces with crisp , bright light. A great choice for a restorative break; yoga and qigong sessions are included in the rate, as well as indoor and outdoor pools, sauna and steam, with a wide selection of massages available (payable on site). Cocktail hour can be taken by the outdoor fire on the bar terrace, with Mediterranean dishes given a Madeira twist and served in a Michelin guide-listed restaurant.
Doubles from £92 B&B; pontadosol.com
Quinta do Furão, Santana
Explore the stunning north coast of Madeira by establishing yourself at this cliff top corner, with sweeping sea views and five hectares of beautifully planted grounds including a large range of vineyards. The bedrooms are crisp and unfussy, the wellness area has an oversized swimming pool and a tempting menu of massages, and dinner in the rustic-looking restaurant – whether on the terrace on warmer evenings, or by the fire if it’s cold – makes the a chance to try a classic. Madeira dishes. Great for hikers, many of Madeira’s wonderful levadas are nearby.
Doubles from £180 B&B; quintadofurao.com
Atrio, Calheta
Billing itself as an island within an island, Atrio is a beautiful bucolic escape, run by Emmanuelle and Mickael, who have created the kind of hotel they always wanted to stay in. Klafs sauna, heated swimming pool and restaurant which includes a good range of veggie, GF and lactose intolerant options. Beyond the hotel’s lush gardens, the Levada Nova da Calheta is just a 10-minute stroll away – the starting point for a number of walks, with bike hire available and whale watching tours to book. Twenty of the 22 rooms come with lovely sea views, and most are spread through the gardens, each with its own private terrace.
Doubles from £78 B&B; atrio-madeira.com
1905 Zino Palace, Ponta do Sol
Not to be missed is Zino’s – the sparkling, bubblegum-pink mansion perched above the quiet seaside town of Ponta do Sol, designed as a summer home for the Zino family at the turn of the 20th century. It is one of the nicest hotels on the island, with rooms in dusky-pink or sage-green with art deco furnishings and modern touches, and a small pool – also pink – ideal for cooling off after a walk along the nearby levadas. Breakfast continues until midday, with an all-day snack menu, while Ponta do Sol, offering a bit more bustle, is ideal for evening dinner.
Doubles from £148 B&B; 1905zinospalace.com
The Vine Hotel, Funchal
Dark and light meet in Funchal’s pioneering design hotel, with a focus on wine running through everything from the vinotherapy treatments in the Wine Therapy Spa to the floors, each representing a season in the life of a grape. The purple and khaki colors give the interior a modern boudoir feel, balanced out by the quartz roof, with a large infinity pool and 20m hot tub, both with majestic views of Fort São João and the mountains beyond. Bedrooms are minimalist but extremely comfortable and the restaurant Terra is one of the best in town.
Doubles from £164 B&B; hotelthevine.com
Solar da Bica, São Vicente
This small 11-room hotel is located in the beautiful São Vicente valley, which has forest-clad mountains and overhead hiking trails for those looking to get off the grid for a few days. The bedrooms are functional and comfortable, and there is an indoor pool and sauna for soothing aching feet after a day of hiking. But really, it’s all about the location. Outside, the beautiful garden is planted with vegetables, fruit and aromatic herbs, many of which make their way to the breakfast table, and there are two outdoor terraces with beautiful mountain views. A car is quite essential, with good restaurants just a short drive away.
Doubles from £106 B&B; solardabica.pt
Se Boutique Hotel, Funchal
Just steps from the city’s grand 15th-century cathedral, the Se combines all-white bedrooms with bold colors throughout the rest of the hotel—vibrant green in the restaurant, teal-blue on the roof terrace—complete with a sunken lawn. – and an eclectic mix of retro furniture and antiques. Sunset drinks on the rooftop 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 is the perfect restorative treatment after a day of 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 for those who want to experience the best of the Madeira breed of classic country estate hotel. The elegant 18th century quinta is set in 2.5 hectares of blooming botanical gardens, with more than 500 different plant species and some rare and very old trees. Interiors are classic, rather than contemporary, but rooms are light and airy. The Colombo bistro offers relaxed poolside lunches, while the Beresford restaurant serves traditional Madeira dishes in an impressive dinner style.
Doubles from £233 B&B; jardinsdolago.com