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Check availability on Pienza Family-Friendly Hotels

Our top choices for Pienza family-friendly hotels

Free daily continental breakfast
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
Outdoor pool
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
Breakfast, lunch, dinner served; local cuisine
Hotel San Gregorio

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is 5.362.236 ₫
6.082.595 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio
Seasonal outdoor pool
Podere Spedalone

Podere Spedalone

Podere Spedalone
1.0 star property
Pienza
9.4 out of 10, Exceptional, (42)
"Amazing food, amazing views"
United States
Juan
Podere Spedalone
Land view from property
Hotel Corsignano

Hotel Corsignano

Hotel Corsignano
4.0 star property
Pienza
9.4 out of 10, Exceptional, (330)
"Enjoyed the hotel. Great location, quality breakfast and rooms."
United States
Joseph
The price is 3.487.196 ₫
4.019.892 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel Corsignano
Garden
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 3.087.743 ₫
3.488.505 ₫ total
includes taxes & fees
12 Dec - 13 Dec
Borgo Sant'Ambrogio Resort
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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Frequently asked questions

What's Pienza like for family-friendly holidays?
The destination of Pienza is a good option if you've been considering a getaway with the children. The castle here makes this an attractive holiday spot for families.
How many family hotels will I find in Pienza?
Expedia has 10 family-friendly hotels and other accommodation options in Pienza.
When's the best time to book a family-friendly holiday in Pienza?
The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Pienza is 1065 mm.
What's there to see and do with your family in Pienza?
While you are visiting Pienza, you may want to round up the youngsters and make time to see interesting attractions such as Palazzo Piccolomini, Historic Centre of Pienza and Museo Diocesano. Make sure that you have lots of time for activities such as Palazzo Borgia and Artemisia Gallery.