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Check availability on Pienza Family Hotels

Our top choices for Pienza family-friendly hotels

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
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
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 ￥23,766
￥27,235 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hotel Corsignano
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 ￥31,487
￥35,731 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hotel San Gregorio
Outdoor dining
Suite Gioconda - Podere Casa Rossa in Pienza

Suite Gioconda - Podere Casa Rossa in Pienza

Suite Gioconda - Podere Casa Rossa in Pienza
Pienza
10.0 out of 10, Exceptional, (4)
"Comfortable, clean and the hosts are over the top welcoming! Walking distance to Pienza with gorgeous views. Loved staying here and hope to come back someday! "
United States
Doug H.
The price is ￥29,358
￥39,381 total
includes taxes & fees
Dec 23 - Dec 24
Suite Gioconda - Podere Casa Rossa in Pienza
Exterior
The house in the village - Angelica apartment - Vald'Orcia

The house in the village - Angelica apartment - Vald'Orcia

The house in the village - Angelica apartment - Vald'Orcia
Monticchiello
10.0 out of 10, Exceptional, (11)
"Nice and comfortable house in a beautiful tiny village "
United States
Lana A.
The price is ￥16,237
￥19,881 total
includes taxes & fees
Dec 21 - Dec 22
The house in the village - Angelica apartment - Vald'Orcia
Outdoor dining
Il Podere di Casa Rossa Pienza

Il Podere di Casa Rossa Pienza

Il Podere di Casa Rossa Pienza
Pienza
10.0 out of 10, Exceptional, (3)
"Wonderful views, accommodating hosts"
United States
Pete and Alison C.
The price is ￥32,862
￥46,554 total
includes taxes & fees
Dec 21 - Dec 22
Il Podere di Casa Rossa Pienza
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 ￥16,152
￥18,315 total
includes taxes & fees
Dec 14 - Dec 15
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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Family-friendly hotels with free breakfast in Pienza

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)
Hotel Relais II Chiostro di Pienza
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 Pienza Hotel Reviews

Abbadia Sicille Relais

Abbadia Sicille Relais

10/10 Excellent
"Room was beyond expectations. Helpful staff and overall great experience. "
Robert 1-night trip
Posted 5 days ago
Abbadia Sicille Relais

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Frequently asked questions

What's Pienza like for family-friendly vacations?
The destination of Pienza is a good option if you've been considering a getaway with the kids. The castle here makes this an attractive vacation spot for families.
What's the best accommodation for a family vacation in Pienza?
Hotel Corsignano is a hotel with a restaurant and free parking, and it's a top choice on Expedia for families. Other good choices to stay with the kids include Podere Spedalone and Agriturismo Il Macchione.
How many family-friendly hotels are there in Pienza?
Expedia has 10 family-friendly hotels and other accommodations in Pienza.
When's the best time to book a family-friendly vacation in Pienza?
The hottest months are usually August and July with an average temp of 69°F, while the coldest months are January and February with an average of 42°F. Average annual precipitation for Pienza is 42 inches.
What's there to see and do with your family in Pienza?
While you are visiting Pienza, you might want to round up the kiddos and make time to see interesting attractions such as Palazzo Piccolomini, Historic Centre of Pienza, and Museo Diocesano. Make sure you have lots of time for activities like Palazzo Borgia and Artemisia Gallery.