Tuscany, Italy

Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco Photos

Winter Villas rate with breakfast

Includes
  • Breakfast
  • Continental Breakfast Delivered to the Villa
  • Welcome Tuscan hamper of groceries upon arrival
  • Concierge upon request
  • Land Rover Defender, or similar type of 4x4 vehicle, for guests to drive for the duration of their stay
  • Smith Extra: A wine-tasting tour for two
Offer details

Available to book until 20 Mar 2026

Valid for stays from 7 Jan 2026 to 20 Mar 2026

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

50% (including tax) will be taken at the time of booking. The balance (including tax) will be taken 14 days before arrival.

Cancellation Policy

Please be aware that cancellations made later than 1 hour after booking will incur a charge of 50 percent. Please be aware that cancellations made less than 14 days before arrival will incur a charge in full.

10 room types available for this offer
Photo of Villa Alba

Villa Alba

  • 6guests
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.
Photo of Villa Oliviera

Villa Oliviera

  • 6guests
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.
Photo of Villa Castello

Villa Castello

  • 6guests
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.
Photo of Villa Casa del Fiume

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.
Photo of Villa Gauggiole

Villa Gauggiole

  • 8guests
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.
Photo of Villa Chiusa

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.
Photo of Villa Stabbi

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.
Photo of Villa Sant’Anna

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.
Photo of Villa Biondi

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.
Photo of Villa Oddi

Villa Oddi

  • 5guests
Bright and light with chic contemporary furnishings and traditional features, such as vaulted roofs and Tuscan fireplaces, this 445sq m six-bedroom (some with four-poster beds) villa is perfect for group stays. Guests have use of a private tennis court, heated infinity pool and a home cinema. There’s a living room, dining and laundry areas and a kitchen (with a wood-burning oven, fridge, pots and pans, cutlery and crockery). All bedrooms have ensuites and one twin room is set in the peaceful pool house close by. Two extra beds can be added on request (free for under-13s). There are sweeping views of Montalcino’s countryside and the villa has LCD flatscreen TVs in the living room and all bedrooms, a PlayStation 4, Apple TV, air-conditioning and WiFi.

Other offers

Stay 4 nights, pay 3 - Villas

Includes
  • Breakfast
  • Your Tuscan Dispensa - Welcome grocery upon arrival
  • Included in the nightly Villa rate is a 7-seat Land Rover Defender, or similar type of 4x4 vehicle, for guests to drive for the duration of their stay
  • Complimentary newspaper application for Android and Apple devices
  • Smith Extra: A wine-tasting tour for two
Offer details

Valid for stays from 9 Oct 2024

Minimum stay 4 nights

Offer price per night from $14,513.09

Best-price guarantee

View offer

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)

Stay 4 nights Pay 3

Includes
  • Smith Extra: A wine-tasting tour for two
Offer details

Valid for stays from 11 Apr 2025

Minimum stay 4 nights

Price per night from Offer prices per night from
$1,511.39 $1,230.48

Best-price guarantee

View offer

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)

Spring Getaway : Save 15% with Half board

Includes
  • Breakfast
  • Daily breakfast for two
  • Daily lunch or dinner at Osteria La Canonica for two (excluding alcoholic beverages)
  • One Classic Wine Tour at our on-site Castiglion del Bosco winery for two
  • Smith Extra: A wine-tasting tour for two
Offer details

Valid for stays from 11 Apr 2025

Minimum stay 2 nights

Maximum stay 7 nights

Offer price per night from $1,744.27

Best-price guarantee

View offer

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)

Villa Sojourn offer with half board

Includes
  • Breakfast
  • Dinner
  • Lunch or dinner each day at one of our restaurants, or as an in-Villa dining experience prepared by one of our Chefs (alcoholic beverages excluded)
  • Land Rover Defender, or similar type of 4x4 vehicle, for guests to drive for the duration of their stay
  • All minibar items, which are replenished daily (alcoholic beverages excluded)
  • Smith Extra: A wine-tasting tour for two
Offer details

Valid for stays from 20 Sep 2025

Price per night from Offer prices per night from
$14,067.12 $11,820.99

Best-price guarantee

View offer

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)