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Check availability on Castiglione del Bosco Family-Friendly Hotels

Our top choices for Castiglione del Bosco family-friendly hotels

Ice skating
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (69)
"Wonderful stay "
United States
Talib
The price is 36.134.292 ₫
40.056.561 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Castiglion del Bosco, A Rosewood Hotel
Hiking
Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
5.0 star property
Trequanda
9.8 out of 10, Exceptional, (97)
"It was very clean, excellent service and communication with every staff member was great, location was incredible, and overall a very pleasant stay. If you have the opportunity, the stay is great!"
United States
Juan Carlos
The price is 4.459.651 ₫
4.998.268 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Borgo Sant'Ambrogio Resort
Aerial view
Hotel Athena

Hotel Athena

Hotel Athena
4.0 star property
Siena Historical Center
9.2 out of 10, Wonderful, (1008)
"Excellent hotel, very helpful staff, highly recommended "
United States
Vikram
The price is 2.319.080 ₫
2.643.671 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Hotel Athena
Breakfast meal
Palazzo Ravizza

Palazzo Ravizza

Palazzo Ravizza
4.0 star property
Siena Historical Center
9.4 out of 10, Exceptional, (746)
"We enjoyed our stay here."
United States
LAURIA
The price is 2.729.023 ₫
3.094.577 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Palazzo Ravizza
Indoor pool, open 9:00 AM to midnight, pool loungers
Albergo San Biagio

Albergo San Biagio

Albergo San Biagio
3.0 star property
Montepulciano
8.6 out of 10, Excellent, (200)
"Great place to stay"
Canada
Robert
The price is 16.777.037 ₫
18.578.277 ₫ total
includes taxes & fees
31 Dec - 1 Jan 2026
Albergo San Biagio
Terrace/patio
Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo
Roccastrada
10.0 out of 10, Exceptional, (1)
"Everything about this place is perfect, highly recommend."
United States
Ian
The price is 2.362.627 ₫
2.598.889 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Historic Farmhouse Casa del Chiodo
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool loungers
Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza
4.0 star property
Pienza
8.8 out of 10, Excellent, (630)
"Excellent location in the heart of pienza old town, the view to the Toscana hills and valleys was unique, great experience staying in this hotel "
United States
Pedro
Hotel Relais II Chiostro di Pienza
Deluxe Double Room | Premium bedding, desk, laptop workspace, soundproofing
Affitacamere Maria Gabriella

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (51)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella
View from property
Agriturismo Il Macchione

Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
9.6 out of 10, Exceptional, (56)
"The owners and staff are hospitable .and accommodating very warm people "
Canada
aileen
Agriturismo Il Macchione
Seasonal outdoor pool, pool umbrellas, pool loungers
Antico Casale L'Impostino

Antico Casale L'Impostino

Antico Casale L'Impostino
Civitella Paganico
9.6 out of 10, Exceptional, (39)
"The pool was great, the room was a great size and clean and breakfast was good."
Canada
Tresa
Antico Casale L'Impostino
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.
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Top Castiglione del Bosco Hotel Reviews

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Frequently asked questions

What's Castiglione del Bosco like for family-friendly holidays?
The historic destination of Castiglione del Bosco is a great choice if you've been considering a holiday with the children. The restaurants here makes this an attractive holiday spot for families.
When's the best time to book a family-friendly holiday in Castiglione del Bosco?
The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Castiglione del Bosco is 944 mm.
What's there to see and do with your family in Castiglione del Bosco?
While you and your family are staying in Castiglione del Bosco, you may want to visit some family-friendly attractions such as Terme Petriolo, Historic Centre of Pienza and Palazzo Piccolomini. Make sure that you have lots of time for activities such as Museum of Brunello and Torrenieri Montalcino Station.