A bucolic hinterland of rolling hills and plains, Portugal’s Alentejo region beckons with a new breed of countryside hotels that offer a sophisticated update to the rural retreat. Debbie Pappyn checks in to five of the best.
Photographs by David de Vleeschauwer

Flanked by grape vines, Herdade da Malhadinha Nova’s seven-suite Casa do Ancoradouro sits at the highest point of the 450-hectare estate.
The northwestern edge of Alentejo is just a short drive from downtown Lisbon, but once you’ve crossed the Vasco da Gama Bridge over the Tagus River, it might as well be a world away. Stretching from southern Portugal’s Atlantic coast to the borders of Spain, this is a deeply rural region of red earth and rolling hills, vineyards and olive groves, and the occasional limewashed village or ancient hilltop castelo. “Calma, calma” is the credo here — don’t stress, don’t worry, don’t rush if you don’t have to.
While agriculture still dominates life in Alentejo, which produces almost half of Portugal’s wine as well as a sizable share of the global cork harvest, tourism has finally caught on as well, thanks to a new generation of hoteliers who have refitted old herdades or montes (farming estates) — or in some cases built faithful facsimiles — as country retreats complete with spas, sparkling pools, farm-to-table food, and an impressive roster of activities. Brimming with Alentejan authenticity, these sprawling properties also promise what are perhaps the greatest luxuries of all: silence, space, and a pervading sense of calma.

Left to right: São Lourenço do Barrocal’s main house; a staff member heads to the herb garden.

Left to right: Meals at São Lourenço do Barrocal feature garden-grown vegetables; the same estate’s bar lounge inhabits an old olive press.
São Lourenço do Barrocal
Fourteen years in the making, this pitch-perfect restoration of a 19th-century farming estate near the Spanish border oozes understated pastoral elegance. Eighth-generation owner José António Uva, a retired investment banker, hired Pritzker Prize–winning architect Eduardo Souto de Moura to resuscitate and transform the property’s village-like cluster of cottages, barns, and stables into a 40-room hotel, its whitewashed interiors furnished simply but meticulously with restored and bespoke pieces. Situated on 780 hectares of gnarled cork oaks and olive trees interspersed with vineyards, the estate, which opened to guests in the spring of 2016, provides plenty of opportunities to connect with the countryside — everything from guided nature walks and horseback riding to fishing on nearby Lake Alqueva and taking part in olive and grape harvests. The picturesque castle town of Monsaraz is also close at hand.
Diversions at the hotel proper are equally varied. There’s a vaulted Susanne Kaufmann spa, a bar housed in a converted olive mill, a meadow-side swimming pool, and a farm-to-fork restaurant serving elevated Alentejano fare like pork neck with asparagus migas (breadcrumbs fried with garlic and paprika) made with herbs and vegetables from an organic kitchen garden. Guests can also visit the on-site winery for tours and tastings, or stock up on estate wine, olive oil, and local pottery and textiles at the hotel shop. Still, the main draw of São Lourenço do Barrocal is its wide-open spaces, and the chance to experience the country life much as Uva’s forebears did — if not quite so rustically (doubles from US$260; barrocal.pt).

An ancient olive grove on the grounds of São Lourenço do Barrocal.

Left to right: The lobby lounge at L’And Vineyards; staff outside L’And’s Monte do Freixo Poente, a three-bedroom former homestead situated 18 kilometers from the main resort.
Monte do Freixo Poente
Just an hour’s drive east of Lisbon near the hilltop town of Montemor-o-Novo, L’And Vineyards resort has much to recommend it: sleek modernist architecture, a Michelin-starred restaurant, a vinotherapy-centric spa, and 30 villas and suites (some with retractable bedroom skylights for guests who want to sleep under the stars) designed by Brazilian architect Marcio Kogan. But the jewel in this decade-old retreat’s crown is Monte do Freixo Poente, a refurbished three-bedroom homestead that L’And added to its accommodation offerings in 2019. Ideal for families or groups of friends looking for an air of rural seclusion, the house overlooks its own working estate — an undulating swath of oak groves and pastureland for merino sheep and black pigs — some 15 minutes from the main hotel. Cool terra-cotta floors and artisanal accents (like lovely wool rugs loomed in regional villages) add to the authentic rural vibe, with the added comforts of an outdoor swimming pool and a spacious sitting and dining room equipped with a suspended fireplace and kitchenette. But for all the house’s pared-back luxury, nothing beats just sitting on the shady veranda and gazing out across the gently rolling Alentejan countryside (US$400 per night, exclusive use; l-and.com).

Crisp lines and alfresco meals with a view are part of the appeal at Dá Licença.

Dá Licença’s art-filled interiors compliment the idyllic rural setting.
Dá Licença
The land on which this intimate, art-filled refuge stands once belonged to nuns from the convent in nearby Estremoz, and later to one of the region’s top olive-oil cooperatives. By the time its current owners, Vitor Borges and Franck Laigneau, happened upon the estate in search of a holiday home, the old hilltop olive farm was abandoned and falling into ruins. But the pair fell in love with the place nonetheless, enchanted as much by its heritage as by the peaceful setting. After acquiring the property, they left their careers in Paris (where Borges, a native Portuguese, was director of textiles at Hermès and Laigneau ran a gallery) to focus on developing it into a hotel. The result is a beautifully realized conversion of three century-old farm buildings complemented by a huge moon-shaped swimming pool and an art gallery.
There are just nine suites, some in the main house, others in the former barn and stables. Individually designed, they boast limewashed walls and swaths of local granite and marble; they’re also punctuated by antique and vintage Scandinavian Jugendstil (a variant of art nouveau) and anthroposophical design pieces collected by Laigneau over the course of two decades. There’s no restaurant per se, but the resident chef can prepare lunches and dinners with enough notice. The owners are just as happy to point their guests in the direction of the many good dining establishments in Estremoz. “It’s all about connecting with the essence of the Alentejo,” Borges says (doubles from US$450; dalicenca.pt).

An equestrian guide on one of Herdade da Malhadinha Nova’s purebred Lusitano horses.
Herdade da Malhadinha Nova
Deep in the languid hinterland of the lower Alentejo, Herdade da Malhadinha Nova has evolved considerably since the Soares family bought the abandoned estate in 1998, first opening a winery, then a restaurant, a stud farm, and eventually a smart farmhouse hotel. Its latest incarnation has seen the addition of 16 suites in a handful of new villa units — including the seven-room Casa do Ancoradouro, complete with its own library, wine bar, and grand piano — scattered about the 450-hectare property. (Malhadinha Nova also operates a four-bedroom house in the nearby village of Albernoa.) Interiors vary among the villas, but all feature a thoughtful blend of commissioned work from old-school artisans (pottery, baskets, bulrush chairs) and designer pieces by the likes of Umut Yamac and Marcel Wanders.
Apart from making some terrific wines, the estate produces its own olive oil, fruit, honey, eggs, beef, pigs, and lamb, all of which make it onto the menu of the hotel restaurant, which is overseen by chef Joachim Koerper of Lisbon’s Michelin-starred Eleven. Private picnics in the vineyards can also be arranged. While the roster of activities includes everything from hot-air balloon rides to canoeing sessions, the best way to explore the property is in the saddle: many of the estate’s stable of pure-blood Lusitano horses are available for leisurely rides through the fields and cork-oak forests of this remarkable slice of Portuguese countryside (doubles from US$340; malhadinhanova.pt).

Left to right: Herdade da Malhadinha Nova produces its own organic honey; details in a guest room.

Left to right: The property has been built amid a sprawling farm; a bedroom at the same estate.

Poolside cottages at Craveiral Farmhouse.
Craveiral Farmhouse
This unassuming country hotel lies some 12 kilometers inland from the dramatic shores of the Costa Vicentina and the seaside parish of Zambujeira do Mar, where life still moves at a blissfully slow pace. Owner Pedro Franca Pinto, a Lisbon-based lawyer, opened Craveiral in 2018 with the idea of creating an eco-friendly refuge as much for himself as for likeminded guests. Three clusters of low-slung, farmhouse-style buildings arranged around courtyards contain 38 rooms and one- or two-bedroom cottages, some with freestanding cork baths and minimalist pieces from Portuguese furniture makers WeWood and Dam. There’s also a hammam-equipped wellness center.
Yet beyond its luxury trappings, Craveiral is an earnest agricultural enterprise. Pinto has rehabilitated the nine-hectare property — a former carnation (craveiral) farm — with the planting of over 1,000 native fruit trees and an extensive vegetable garden, which, together with locally sourced game and seafood, provide most of the ingredients for the elegant in-house restaurant. (Wood-fired cooking is the highlight here, but don’t miss the dreamy desserts by pastry chef Matilde Urbano.) Come evening, the aromas from the kitchen mingle with the scent of olive trees and wildflowers carried on cool breezes from the coast (doubles from US$235; craveiral.pt).

Craveiral Farmhouse owner Pedro Franca Pinto.
This article originally appeared in the March/May 2022 print issue of DestinAsian magazine (“At Home in Alentejo”).