Tuscany, Italy

Rosewood Castiglion del Bosco

Luxury Tuscan Villa Escape for 2020

Includes
  • A Tuscan hamper of welcome groceries upon arrival
  • Daily housekeeping service; extra cleaning, if required, will be charged at cost
  • 24-hour security assistance
  • Virtual concierge on call
  • Your own private heated infinity swimming pool with salted water
  • Complimentary newspaper application for Android and Apple devices
  • Smith Extra: A wine-tasting tour for two
Offer details

Available to book until 28 Oct 2020

Valid for stays from 1 Jul 2020 to 31 Oct 2020

Minimum stay 4 nights

Terms & Conditions

Booking this Offer

Select your dates from the calendars below the room images to check availability and prices. To book by phone, call us on 1 800 464 2040 and mention the offer name.

Please note that this offer is subject to availability and black-out dates may apply. The hotel may withdraw this offer at any time and without notice.

Deposit Policy

Rosewood Castiglion del Bosco requires a deposit of 50% of the booking total, which will be charged to you directly by the hotel. The remaining balance is due prior to arrival. To confirm a villa booking from 24 March to 26 November, the hotel requires a 50% deposit at the time of booking and full prepayment 30 days before arrival. For winter stays in villas, a 50 per cent non-refundable deposit is required when booking; the remaining balance is due 13 days before arrival.

Cancellation Policy

Please be aware that cancellations made less than 30 days before arrival will incur a charge of 50 percent.

9 room types available for this offer

Villa Alba

  • 5guests
This 225sq m hilltop villa sits among lavender-filled gardens and ancient trees, with an open-air heated pool and a pergola-shaded furnished terrace; which overlook Val d’Orcia Natural Park. There are two bedrooms in the main villa: a master bedroom (with a king-size bed) and a second bedroom with twins (an extra bed can be added to this room, on request). If more than two guests are staying, extra beds are charged €200 a night for guests aged 13 and over (free for under-12s. A baby cot can be added free to each room and, all bedrooms have ensuites. There’s a living room with a fireplace and a dining room with an open-plan kitchen; complete with a stove and cooking utensils. Flatscreen TVs (in the living room and each bedroom), a minibar and free WiFi are included as well as a small laundry room. The separate Guest House (available on request only) can accommodate another two people.

Villa Oliviera

  • 5guests
Formerly an olive-oil press, this 417sq m villa sits on a hilltop overlooking the surrounding countryside, with glimpses of Montalcino, from a private pergola-shaded furnished terrace and heated infinity pool. The villa is decorated in a contemporary country style with cream walls and a terracotta-tiled floor. There’s a living room with a Tuscan-style fireplace, a dining room, kitchen, two powder rooms and a laundry room; and a master bedroom, a double bedroom and a twin bedroom (all with walk-in closets and ensuites). Three extra beds can be added on request; the first two are free for under-13s. Flatscreen TVs (in each living room and bedroom), a minibar and free WiFi are included.

Villa Castello

  • 5guests
This villa sits next to mediaeval castle ruins on a hillock, which overlooks breathtaking Tuscan scenery – which you can gaze at from the garden, the pergola-shaded furnished terrace and the open-air heated pool. Alongside a living room with a large Tuscan fireplace, a kitchen and a laundry room, there’s a double bedroom and a twin bedroom on the first floor and a master bedroom with a walk-in closet on the second floor (all with ensuites). An extra bed can be added on request; it's free for under-13s. A 17th-century wood-fired pizza oven sits just outside the villa and flatscreen TVs (in the living room and each bedroom), a minibar and free WiFi are included.

Villa Casa del Fiume

  • 5guests
From this 137sq m villa’s private tennis court and heated swimming pool, and furnished terrace, you can enjoy blissful bucolic views of Montalcino and Il Borgo. Decorated in a regal rustic style – with floor-to-ceiling portraits, cream walls and Louis XVI-style antique furnishings – this villa has a living room with an authentic Tuscan fireplace, a dining room, two powder rooms, a laundry area and a kitchen; which has an oven, but you may prefer to use the 17th-century wood-fired pizza oven located outdoors. The main house has a master bedroom with a king-size bed and two twin bedrooms (all with ensuites); and the 137sq m Pool House has a double bedroom with a king-size bed, living room with a fireplace, a kitchenette, two bathrooms and a laundry area. Four extra beds can be added on request; the first two are free for under-13s. Flatscreen TVs (in each living room and bedroom), a minibar and free WiFi are included.

Villa Gauggiole

  • 5guests
Decorated in a refined rustic style, this 446sq m villa (the former home of a farming family) has exposed wooden beams, terracotta-tiled floors and antique furnishings. Outside, there's a private, heated open-air pool and an outdoor wood-fired pizza oven dating back to the 17th century; views of the surrounding vineyard can also be enjoyed from the poolside day-beds. The main house has a living room with a fireplace, dining area and open-plan kitchen (with a traditional aga), a laundry room, two powder rooms, a master bedroom, double bedroom and twin bedroom, all with ensuites. The 76sq m Guest House sleeps two in a double bedroom with a fireplace and an ensuite, and the 59sqm Pool House has a living room with a fireplace, a kitchenette and a bathroom. Four extra beds can be added on request; the first two are free for under-13s. Flatscreen TVs (in each living room and bedroom), a minibar and free WiFi are included.

Villa Chiusa

  • 5guests
This 362sqm villa was formerly a police station, but has been converted into a stylish stay with a private open-air infinity pool and a furnished terrace with views of Montalcino. In the main house, there’s a living room with a Tuscan-style fireplace, a library and TV room, dining room, laundry room, two powder rooms, a kitchen, master bedroom with a walk-in closet, double bedroom and a twin bedroom (all bedrooms have ensuites). The 47sq m Guest House is available for two guests for an additional cost (price on request); it has a double bedroom with a king-size bed and an ensuite, and the 37sq m Pool House has a kitchenette and bathroom. There's also space for two extra beds on request (free for under-13s). Flatscreen TVs (in the living room and each bedroom), a minibar and free WiFi are included.

Villa Stabbi

  • 5guests
Located high on a ridge overlooking the golf course, this 474sq m villa has a heated outdoor pool and furnished terrace with sweeping views of the Sienese countryside. It’s decorated in a rustic-chic style, with exposed wooden beams, large arched windows and grand 17th-century-style portraits. In the main house there’s a living room with a Tuscan fireplace, a dining room, powder room and kitchen; and a master bedroom, double bedroom, twin bedroom and a single bedroom (all with ensuites). Four extra beds can be added on request; the first two are free for under-13s. The 62sq m Guest House has a double bedroom with an ensuite and a terrace, and the 50sq m Pool House has a living room with a fireplace and a bathroom. Flatscreen TVs (in each living room and bedroom), a minibar and free WiFi are included, and there’s a working, outdoor, 17th-century wood-fired pizza oven.

Villa Sant’Anna

  • 5guests
Perched on a ridge overlooking the golf course, this luxurious villa has an outdoor heated pool and a furnished pergola-shaded terrace with views of the surrounding Sangiovese vineyards. This 587sq m rustic-chic villa’s interiors have a contemporary twist with elegant furnishings and cream walls. The main house has a living room with a Tuscan-style stone fireplace, a library and games room, home cinema, dining room, powder room, laundry room and a kitchen; and a master bedroom, two double bedrooms, a twin bedroom and a single bedroom (all with ensuites). Three extra beds can be added on request; the first two are free for under-13s. There are extensive gardens with a private tennis cort, and the 68sq m Pool House has a living room with a fireplace and a bathroom. Flatscreen TVs (in each living room and bedroom), a minibar and free WiFi are included, and there’s a working, outdoor, 17th-century wood-fired pizza oven.

Villa Biondi

  • 5guests
This villa – decorated in an elegant rustic style with terracotta ceilings, exposed beams and cast-iron four-poster beds – has 693sq m of floor space as well as a separate 32sq m Pool House (with a kitchenette and bathroom). Located on a cypress-lined venue that runs alongside the golf course, the villa features a heated open-air pool and a pergola-shaded furnished terrace. There’s a living room with a large Tuscan fireplace, a library, dining area, two powder rooms, a laundry room and kitchen. Five bedrooms (a double bedroom with a king-size bed and a twin bedroom on the ground floor; a master bedroom with a walk-in closet, double bedroom and twin bedroom on the first floor – all with ensuites) make this villa perfect for a family stay. Three extra beds can be added on request; the first two are free for under-13s. Flatscreen TVs (in the living room, library and each bedroom), a minibar and free WiFi are included.

Other offers

Truffle Hunting Package

Includes
  • Breakfast
  • A Truffle Hunting expedition
  • Transfer from/to the Truffle Hunting
  • Truffle cooking class followed by a meal with dishes prepared are offered to discover and savour the delights of the region.
  • A Tuscan hamper of welcome groceries upon arrival
  • Smith Extra: A wine-tasting tour for two
Offer details

Available to book until 20 Dec 2020

Valid for stays from 16 Sep 2020 to 20 Dec 2020

Minimum stay 2 nights

Offer price per night from $4,166.20

Price information

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)