Tuscany, Italy

Rosewood Castiglion del Bosco Villa Sant’Anna

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

Booking this Offer

Select your dates 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.

14 room types available for this offer

Villa Sant’Anna

  • 5 guests

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.

Enter dates to see prices and availability

Book this room

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

Price per night from Offer prices per night from
$3,477.91 $2,608.44

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
$1,052.65 $619.94

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 $3,520.81

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 three nights or more and receive every third night complimentary

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

Valid for stays from 8 Jun 2026

Minimum stay 3 nights

This is an on request offer, call us to check availability

1 800 464 2040
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)