Castiglione del Bosco Travel Guide

Tourist Guide

Beautiful view of the hotel pool (a number of the villas have their own pools) from a terrace above, with the Tuscan hillside in the background.
Beautiful view of the hotel pool (a number of the villas have their own pools) from a terrace above, with the Tuscan hillside in the background.
Main pedestrian walkway through the property (was originally a small hill-town). This place is so beautiful.
Probably among the top 3 vacation properties I've seen/stayed. There is over the top, and then there is over that top! I'm not being facetious, this place is stunningly beautiful, and this (picture) is among the nicest golf courses (on the property) in Italy.  Beautiful grounds, stand alone villas, tennis, golf, Brunello vineyards/winery, golf, and all ridiculously, stunningly beautiful.  If you want to go big, and really treat yourself, go here!
Rosewood Castiglion del Bosco, Villa Stabbi on this pic. The most amazing hotel resort in Tuscany or perhaps the whole of Italy...
Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Localita Castiglion del Bosco Montalcino SI
Stay at this luxury hotel in Montalcino. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions Castiglion del Bosco Winery and Corte Pavone ...
9.8/10 Exceptional! (73 reviews)
Wonderful stay

Reviewed on 25 Nov 2025

Rosewood Castiglion del Bosco
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundable
The price is NZ$173 per night from 1 Mar to 2 Mar
NZ$173
1 Mar - 2 Mar
includes taxes & fees
Stay at this business-friendly hotel in Siena. Enjoy free Wi-Fi, free parking and a rooftop terrace. Our guests praise the breakfast and the helpful staff in ...
9.2/10 Wonderful! (1,003 reviews)
Great hotel, beautiful view and excellent service from the personnel.

Reviewed on 28 Jan 2026

Hotel Athena
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

5 out of 5
Banchi Di Sopra 85 Siena SI
The price is NZ$514 per night from 2 Mar to 3 Mar
NZ$514
2 Mar - 3 Mar
includes taxes & fees
Stay at this luxury hotel in Siena. Enjoy free Wi-Fi, 2 bars/lounges and breakfast (surcharge). Our guests praise the helpful staff in their reviews. Popular ...
9.2/10 Wonderful! (578 reviews)
Staff is amazing! The hotel is beautiful! Hotel is very clean and a respite from walking all day! Be sure and ask for different pillows if you are particular... they have many kinds to choose from!

Reviewed on 20 Jan 2026

Grand Hotel Continental Siena – Starhotels Collezione
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Hotel San Gregorio

Hotel San Gregorio

3 out of 5
Via Della Madonnina 4 Pienza SI
Stay at this business-friendly residence in Pienza. Enjoy free Wi-Fi, an outdoor pool and room service. Popular attractions RI Crea RE and Enoteca Di Ghino are ...
9.2/10 Wonderful! (134 reviews)
Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great!

Reviewed on 25 Oct 2025

Hotel San Gregorio
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Piazza San Giovanni, 13 Siena SI
Stay at this residence in Siena. Enjoy free Wi-Fi, breakfast (surcharge) and room service. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.6/10 Exceptional! (195 reviews)
Excellent service! Great communication. A beautiful set up for our family with two rooms. Very accommodating and we loved the slippers. Elevator was great for luggage. A must stay in a beautiful and centrally located area.

Reviewed on 31 Dec 2025

Il Battistero Siena - Residenza d'Epoca
Beautiful stone house with garden and private pool.

Beautiful stone house with garden and private pool.

Sovicille - Siena Toscana
Stay at this holiday home in Siena. Enjoy free Wi-Fi, private pools and a garden. Popular attractions San Leonardo al Lago and Acquacalda Swimming Pool are located ...
9.6/10 Exceptional! (68 reviews)
Lovely house and beautiful gardens in a fabulous part of Tuscany. A very restful property after longs days touring Tuscany, and also fabulous for relaxing days around the house and gardens. The surrounding countryside is also fabulous with plenty of opportunities for good walks and cycling. Tiziana ...

Reviewed on 12 Oct 2025

Beautiful stone house with garden and private pool.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Activities

Cities near Castiglione del Bosco