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
Fully refundableReserve now, pay when you stay
The price is 34.249.064 ₫ per night from 21 Mar to 22 Mar
34.249.064 ₫
37.981.705 ₫ total
21 Mar - 22 Mar
includes taxes & fees
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 ...
Rosewood Castiglion del Bosco
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
The price is 2.923.753 ₫ per night from 18 Mar to 19 Mar
2.923.753 ₫
3.370.057 ₫ total
18 Mar - 19 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! (1,001 reviews)
Clea

Reviewed on 27 Feb 2026

Hotel Athena
Hotel Chiusarelli

Hotel Chiusarelli

3 out of 5
Viale Curtatone 15 Siena SI
The price is 2.470.370 ₫ per night from 13 Mar to 14 Mar
2.470.370 ₫
2.871.428 ₫ total
13 Mar - 14 Mar
includes taxes & fees
Stay at this business-friendly hotel in Siena. Enjoy free breakfast, free Wi-Fi and room service. Our guests praise the breakfast and the helpful staff in their ...
8.8/10 Excellent! (1,001 reviews)
Perfect location … great quality/value … nice staff

Reviewed on 2 Feb 2026

Hotel Chiusarelli
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
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 ...
9.4/10 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 25 Oct 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 Wi-Fi and an outdoor pool. Popular attractions Horti Leonini and Chapel of our Lady ...
Casanova - Panoramic Rooms and Suites
Bosco della Spina

Bosco della Spina

via della Tinaia 13 Murlo SI
Stay at this luxury residence in Murlo. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Castello di Montepescini and La Porta Gallery ...
9.6/10 Exceptional! (169 reviews)
Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing.

Reviewed on 30 Oct 2025

Bosco della Spina
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

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

Find out about the history of Montalcino when you take a trip to 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 studying the exhibits at Museum of Brunello in Montalcino. Discover the area's countryside and spas.

Museum of Brunello

Abbazia di Sant'Antimo

You can learn about the history of Montalcino with a visit to Abbazia di Sant'Antimo. Visit the area's spas or simply enjoy its wineries.

Abbazia di Sant'Antimo

Cities near Castiglione del Bosco

Montalcino featuring a sunset and heritage architecture

Montalcino