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
Fully refundableReserve now, pay when you stay
The price is NT$41,473 per night from Mar 21 to Mar 22
NT$41,473
NT$45,993 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 ...
Rosewood Castiglion del Bosco
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
The price is NT$3,209 per night from Mar 18 to Mar 19
NT$3,209
NT$3,716 total
Mar 18 - Mar 19
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! (1,003 reviews)
Estupenda estadia, el cuarto estaba muy comodo y limpio, nos proporcionaron agua y cafe, el staff muuuy amable, el hotel tiene unas vistas espectaculares y el desayuno buffet, delicioso, ademas de estar en una muy buena ubicacion para recorrer siena sin preocupacion, definitivamente volveria a hospedarme ...

Reviewed on 2026/2/15

Hotel Athena
Hotel Chiusarelli

Hotel Chiusarelli

3 out of 5
Viale Curtatone 15 Siena SI
The price is NT$2,991 per night from Mar 2 to Mar 3
NT$2,991
NT$3,477 total
Mar 2 - Mar 3
includes taxes & fees
Book a stay at this business-friendly hotel in Siena. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,002 reviews)
Perfect location … great quality/value … nice staff

Reviewed on 2026/2/2

Hotel Chiusarelli
See all 3,285 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 2025/10/25

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 WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.6/10 Exceptional! (198 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 2025/12/31

Il Battistero Siena - Residenza d'Epoca
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
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

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

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

Cities near Castiglione del Bosco

Montalcino showing a sunset and heritage architecture

Montalcino