Housed in the main buildings of the Borgo, this room features a master bedroom with bathroom and a sitting corner. It is characterized by warm hues and welcoming atmosphere. Our Deluxe Room features a private terrace overlooking the Tuscan hills.

Outfitted with fine furnishings in shades of the Tuscan countryside, the Junior Suites comprise a master bedroom with bathroom and an airy sitting corner. They are all housed in the main buildings of the Borgo, and some feature a private terrace with views on the surrounding countryside.

The Borgo Suites consist of a large living room and a spacious separate master bedroom with bathroom. Situated in the main buildings of the Borgo, the suites offer airy interiors, sophisticated furnishings and hues of the Tuscan countryside.

Located in the former winery and stables of the Borgo, the Terrace Suites comprise a spacious master bedroom with bathroom, airy living room, walk-in closet and expansive terrace with shady pergola. Furnished in authentic Tuscan hues and imbued with a soft, warm atmosphere, they offer ground-floor access.

The CdB Suites feature a living room and a large master bedroom with a spacious bathroom and walk-in closet. Each is exquisitely furnished and some offer a guest bathroom and private terrace. Housed within the buildings of the Borgo, the suites stand out for their bespoke Florentine pieces and exclusive textiles.

Situated in a detached building, the Villa Fontaccia has two bedrooms, two bathrooms, a kitchenette, a terrace, a large private garden and private access. The interiors are decorated in warm Tuscan hues, exclusive fine fabrics and bespoke artisanal pieces. Its unique location within the heart of the Borgo affords convenience, as well as absolute privacy. 183 sq. m./ 1,969 sq. ft.

Intimately secluded in the estate wood and proudly dominating a breath-taking view over Montalcino, Siena and Pienza, Villa Agresto sits on a panoramic clearing and is surrounded by olive trees and its own private vineyard. Featuring 5 double bedrooms, a fully equipped kitchen, a bright white cozy and embracing living room with original fireplace, and a shaded internal patio. This Villa has a one-of-a-kind infinity pool with a picture-perfect view.

Situated on a quiet hilltop amidst old-growth trees and lush gardens, Villa Alba offers enchanting views over the Val d’Orcia. This former stone farmhouse has been converted into a romantic hideaway with elegant and inviting furnishings. The two-story villa features an open-plan kitchen, panoramic outdoor area for entertaining and separate guest accommodation. 261 sq. m. / 2,819 sq. ft.

Perched atop a hill overlooking the Borgo on the ruins of a medieval castle, the Villa Castello offers one of the coziest interiors on the estate. The three-story retreat also boasts a beautiful swimming pool and a lovely garden with captivating views over the timeless Tuscan landscape. 353 sq. m. / 3,800 sq. ft.

Formerly the village police station, the Villa Chiusa has been carefully restored and converted into a warm, enticing retreat, complete with an elegant guest annex and a pool house. The infinity pool offers breathtaking views over nearby Montalcino. 362 sq. m. / 3,897 sq. ft.

Surrounded by vineyards, Villa Gauggiole was once home to a large farming family. The villa has been beautifully restored to reveal the origins of the building in the stone walls and original ceiling beams. At the same time, modern comforts and luxurious furnishings were added, lending the home an atmosphere of relaxed sophistication. 579 sq. m. / 6,238 sq. ft.

Situated in the undulating green valleys that shape the northeastern part of the estate, Villa Casa del Fiume offers beautiful views over Montalcino to the southeast and the Borgo to the southwest. This once-rustic building has been transformed into an elegant Tuscan country villa, complete with an original 17th-century wood-fired oven and sophisticated furnishings. Approximately 512 sq. m. / 5,518 sq. ft.

Situated on a picturesque ridge overlooking the Tuscan hills, Villa Stabbi enjoys panoramic views over the gently rolling Sienese countryside. The home’s striking interiors feature the original ceiling beams, an inviting central fireplace and large patio doors that open onto a landscape of ancient oak trees and spectacular sunsets. 586 sq. m. / 6,305 sq. ft.

Perched on a ridge overlooking the Castiglion del Bosco golf course and Sangiovese vineyards, Villa Sant’Anna enjoys enchanting views from dawn to dusk. The home’s elegantly understated interiors are notable for their exquisite details, stonework and furnishings. The villa features a reading/home theater room as well as a private tennis court located within its extensive gardens. 655 sq. m. / 7,050 sq. ft.

Villa Biondi is one of the largest and most spacious villas at Rosewood Castiglion del Bosco. It stands on the cypress-lined avenue that runs alongside the golf course. This genuine Tuscan residence offers all of the warmth and intimacy of home, making it ideal for an extended family or group of friends. The two-story retreat also enjoys spectacular sunsets. Approximately 726 sq. m. / 7,815 sq. ft.

The beautiful six-bedroom Villa Oddi exudes sophistication and charm. Suffused with natural light, the home’s interiors are spacious and elegantly furnished. The residence features state-of-the-art technology, a private screening theater, a private tennis court, an infinity pool and breathtaking views of Montalcino. Villa Oddi is perfect for a family reunion or as a private business retreat. 466 sq. m. / 5,016 sq. ft.

Each evening, Ristorante Campo del Drago serves upscale classical Italian dishes drawn from the various regions of Italy and enriched with fresh produce from the organic kitchen garden. The evocative name pays homage to the Piazza del Campo in Siena and was inspired by the single-cru of Brunello di Montalcino produced by the estate’s winery. Outside, the terrace offers stunning views of the deep green hills and sloping woodlands of Montalcino and the renowned Val d’Orcia.

Located in the heart of the Borgo and attached to the church of San Michele, Osteria La Canonica restaurant in Tuscany offers the authentic, warm atmosphere of a Tuscan trattoria. La Canonica features a shaded open veranda overlooking the stunning valley. In this rustic and informal atmosphere, delicious pizzas and focaccia are prepared to order in an ancient open-view wood-fired oven. Seasonal produce from the organic kitchen garden is combined with other natural ingredients and freshly milled oil from Castiglion del Bosco to create traditional Tuscan fare.

An intimate, club-like space imbued by the Italian culture of good wine and cocktails, the CdBar adjoins our Ristorante Campo del Drago. With its al fresco terrace offering ever-changing views of Montalcino and the Val d’Orcia, it’s a perfect aperitivo spot, but equally suited to a nightcap with friends or that special someone.

Fresh, simple Italian delights are never more satisfying than when enjoyed poolside under the warm Tuscan sun. The views of the hilltop town of Montalcino and the UNESCO-protected park of the Val d’Orcia are to be admired any time of day, and there is no more perfect vantage point than from The Pool Bar’s quiet, relaxing setting beside the panoramic infinity pool.

At Rosewood Castiglion del Bosco, it took a few years of welcoming guests and refining how best to communicate our estate’s uniquely Tuscan spirit for us to fully realise that villas are homes – and that means home cooking. Of course you can order in; but room service is never quite going to reproduce the scent of freshly-grated truffles on a twirl of pasta strands straight from the pan, or the aroma of a slow-braised roast as your own private chef takes it, still sizzling, from the oven.

All of the pools within the estate, including the private villa pools, are saline infinity pools which are kept at an ideal 28°C. In keeping with the estate’s Tuscan aesthetic, they are paved in a timeless Tibetan stone that produces a beautiful, inviting water color.

Located at the heart of Il Borgo, the Spa at Rosewood Castiglion del Bosco offers a serene escape from day-to-day life, specialising in unique therapies based on organic ingredients from the Estate. The Spa uses La Prairie treatments and products and provide an extensive range of beauty and wellness treatments as well as in-Suite and in-Villa massages.

Offering panoramic views of the estate’s gently rolling hills, the fitness center features next-generation Technogym® equipment to improve balance, strength and flexibility. Fitness training sessions include aerobics and other exercises that tone the body and strengthen specific muscle groups. Training can be customized in a daily program or mastered with the assistance of a personal trainer in the privacy of one’s villa. Guests can also benefit from specialized fitness training sessions that take place in the estate’s woodlands or from training sessions created specifically for golfers who wish to improve their performance on the course.