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...
Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Localita Castiglion del Bosco Montalcino SI
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 ...
9.8/10 Exceptional! (73 reviews)
Wonderful stay

Reviewed on Nov 25, 2025

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Rosewood Castiglion del Bosco
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
The price is ￥14,766 per night from Feb 22 to Feb 23
￥14,766
￥16,795 total
Feb 22 - Feb 23
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! (1,000 reviews)
It’s very beautiful

Reviewed on Jan 9, 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
Fully refundableReserve now, pay when you stay
The price is ￥44,039 per night from Feb 23 to Feb 24
￥44,039
￥49,561 total
Feb 23 - Feb 24
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! (577 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 Jan 20, 2026

Grand Hotel Continental Siena – Starhotels Collezione
See all 3,179 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 ...
9.2/10 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 Oct 25, 2025

Hotel San Gregorio
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 San Leonardo al Lago and Acquacalda Swimming Pool are ...
9.4/10 Exceptional! (69 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.
ApartHotel Anghel

ApartHotel Anghel

via Paolo Frajese 71 Siena SI
Book a stay at this business-friendly apartment in Siena. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Santa Maria della Scala ...
8.2/10 Very Good! (327 reviews)
Would recommend staying here and will hopefully be back!

Reviewed on Oct 17, 2025

ApartHotel Anghel
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

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

Fortress of Montalcino

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

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

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

Abbazia di Sant'Antimo

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

Torrenieri Montalcino Station

You can take time to visit Torrenieri Montalcino Station during your travels to Torrenieri. Visit the area's spas, or simply enjoy its wineries.

Torrenieri Montalcino Station

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

￥13,039
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Seggiano: Guided Tour of the Olive Grove and Food Tasting

Seggiano: Guided Tour of the Olive Grove and Food Tasting

￥4,585
per adult
Seggiano: Guided Tour of the Olive Grove and Food Tasting
Bottaia

Tasting Tour in One of The Most Beautiful Cellars in the World

￥6,052
per adult
100% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

￥8,253
per adult
Montalcino: Guided Winery Tour and Wine Tasting
Pienza Self-Guided Interactive Walking Tour with Quizzes

Pienza Self-Guided Interactive Walking Tour with Quizzes

￥917
per adult
Pienza Self-Guided Interactive Walking Tour with Quizzes
Tour of the historical cellars in Montepulciano

Tour of the historical cellars in Montepulciano

￥10,820
per adult
Tour of the historical cellars in Montepulciano
See all activities in Castiglione del Bosco

Cities near Castiglione del Bosco

Montalcino showing a sunset and heritage architecture

Montalcino

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