Tuscany, Italy

Rosewood Castiglion del Bosco Villa Oliviera

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

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.

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 $14,445.00

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
$1,400.00 $1,132.57

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 $1,664.23

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
$14,001.13 $11,765.54

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)