Castiglione del Bosco

Travel 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...
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

5 out of 5
Localita Castiglion del Bosco Montalcino SI
The price is ￥203,837 per night from Mar 21 to Mar 22
￥203,837
￥226,052 total
Mar 21 - Mar 22
includes taxes & fees
Book a stay at this luxury hotel in Montalcino. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Castiglion del Bosco Winery and Corte ...
Castiglion del Bosco, A Rosewood Hotel
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
The price is ￥19,061 per night from Mar 9 to Mar 10
￥19,061
￥21,887 total
Mar 9 - Mar 10
includes taxes & fees
Book a stay at this business-friendly hotel in Siena. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,001 reviews)
Clea

Reviewed on Feb 27, 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 ￥50,981 per night from Mar 18 to Mar 19
￥50,981
￥57,911 total
Mar 18 - Mar 19
includes taxes & fees
Book a stay at this luxury hotel in Siena. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (584 reviews)
The best hotel in siena for sure, thank you!

Reviewed on Feb 23, 2026

Grand Hotel Continental Siena – Starhotels Collezione
See all 3,265 properties in Castiglione del Bosco
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
Book a stay at this business-friendly residence in Pienza. Enjoy free WiFi, an outdoor pool, and room service. Popular attractions RI Crea RE and Enoteca Di ...
9.4/10 Exceptional! (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 Oct 25, 2025

Hotel San Gregorio
Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

3 out of 5
Strada Provinciale 146 di Chianciano San Quirico d'Orcia SI
Stay at this residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Horti Leonini and Chapel of our Lady ...
Casanova - Panoramic Rooms and Suites
Beautiful stone house with garden and private pool.

Beautiful stone house with garden and private pool.

Sovicille - Siena Toscana
Stay at this vacation home in Siena. Enjoy free WiFi, private pools, and a garden. Popular attractions Piazza del Campo and San Leonardo al Lago are located ...
9.6/10 Exceptional! (70 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 Oct 12, 2025

Beautiful stone house with garden and private pool.
See all properties in Castiglione del Bosco
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

Castello Banfi

4/5(6 reviews)

You can enjoy a tasting or tour at Castello Banfi during your travels to Poggio alle Mura. Visit the area's spas, or simply enjoy its wineries.

Castello Banfi

Tenuta Greppo Franco Biondi Santi

You can enjoy a tasting or tour at Tenuta Greppo Franco Biondi Santi during your travels to Montalcino. Discover the area's countryside and spas.

Tenuta Greppo Franco Biondi Santi

Fortress of Montalcino

5/5(5 reviews)

Find out about the history of Montalcino with a stop at Fortress of Montalcino. Visit the area's spas, or simply enjoy its wineries.

Fortress of Montalcino

Castiglion del Bosco Winery

You can enjoy a tasting or tour at Castiglion del Bosco Winery during your travels to Castiglione del Bosco.

Castiglion del Bosco Winery

Museum of Brunello

You can spend time exploring the galleries in Museum of Brunello during your travels in Montalcino. Discover the area's countryside and spas.

Museum of Brunello

Abbazia di Sant'Antimo

5/5(55 reviews)

You can learn about the history of Montalcino when you stop by Abbazia di Sant'Antimo. Visit the area's spas, or simply enjoy its wineries.

Abbazia di Sant'Antimo

Things to do

3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

￥14,504
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
From Fiumicino Airport: 1-Way Bus Transfer to Paganico

From Fiumicino Airport: 1-Way Bus Transfer to Paganico

￥1,651
per adult
From Fiumicino Airport: 1-Way Bus Transfer to Paganico
Seggiano: Guided Tour of the Olive Grove and Food Tasting

Seggiano: Guided Tour of the Olive Grove and Food Tasting

￥4,590
per adult
Seggiano: Guided Tour of the Olive Grove and Food Tasting
Montepulciano Gran Tour

Montepulciano Gran Tour

￥2,754
per adult
Montepulciano Gran Tour
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

￥4,590
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Horseback riding in the hills of Montepulciano in Tuscany

Horseback riding in the hills of Montepulciano in Tuscany

￥14,688
per adult
Horseback riding in the hills of Montepulciano in Tuscany
See all activities in Castiglione del Bosco

Cities near Castiglione del Bosco

Montalcino showing a sunset and heritage architecture

Montalcino

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