A historic square with a prominent tower and statues.

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Check availability on Pienza Family-Friendly Hotels

Tonight
26 Sept - 27 Sept
Tomorrow
27 Sept - 28 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Our top choices for Pienza family-friendly hotels

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.
A swimming pool with a water feature, surrounded by greenery and a table with chairs.
A modern bathroom with two sinks, a shower, and a toilet.
A buffet with various desserts and pastries, a painting on the wall, and wooden paneling.

1. Hotel San Gregorio

Hotel San Gregorio
Pienza
  • Tuscan residence welcomes families with outdoor pool, hot tubs, and optional babysitting services just steps from Palazzo Piccolomini.
Rp3.455.989
Rp3.923.895 total
includes taxes & fees
6 Oct - 7 Oct
Hotel San Gregorio
Two people sitting at a round table outdoors with a scenic view of mountains in the background.
A bar area with a wooden bar counter, three orange chairs, and a variety of bottles and glasses.
A breakfast buffet with various food items and beverages.
A hotel entrance with a sign reading "Hotel Corsignano," a paved driveway, and a large terracotta pot.

2. Hotel Corsignano

Hotel Corsignano
Pienza
  • Families find paradise with babysitting services, bicycle rentals, and two hot tubs just steps from Pienza's historic treasures.
Rp3.452.331
Rp3.919.953 total
includes taxes & fees
19 Oct - 20 Oct
Hotel Corsignano
A room with a green cabinet, a mirror, a sink, and a television.
A bedroom with a bed, a nightstand, a lamp, a chair, a table, and a window with a view of greenery.
A cozy dining area with a table set for four, surrounded by wooden chairs and a patterned tablecloth.
A patio area with outdoor seating, potted plants, and a view of the landscape.

3. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
Rp1.976.377
Rp2.681.591 total
includes taxes & fees
7 Oct - 8 Oct
Affitacamere Maria Gabriella
A villa with a swimming pool, terraced garden, and a view of distant mountains.
A stone building with a gravel pathway leading to the entrance.
A fire pit with burning logs, surrounded by stone blocks and a metal grill.
A cozy living room with a fireplace, comfortable seating, and a table set with various desserts.

4. Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
  • Splash into family fun at this Pienza retreat where kids adore the playground while parents unwind poolside at the winery.
Rp3.583.307
Rp4.023.210 total
includes taxes & fees
27 Oct - 28 Oct
Agriturismo Il Macchione
A swimming pool with a stone wall and a metal ladder, surrounded by trees and a clear sky.
A restaurant with a rustic interior, featuring exposed brick arches, wooden beams, and a bar area in the background.
An outdoor dining setup with various dishes on rustic wooden tables, set against a scenic backdrop of rolling hills and a sunset.
A rustic villa with traditional architecture, surrounded by olive groves and a mountainous backdrop.

5. Podere Spedalone

Podere Spedalone
Pienza
  • This Tuscan farm stay delights families with seasonal outdoor pool, hiking trails, and complimentary breakfast buffet each morning.
Rp2.797.697
Rp3.159.038 total
includes taxes & fees
25 Oct - 26 Oct
Podere Spedalone
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.
A cozy reading room with a fireplace, bookshelves, and comfortable seating.
A cozy living room with a sofa, coffee table, TV, bookshelves, and a decorative lamp.
A swimming pool with sun loungers and umbrellas, surrounded by lush greenery and a house with a tiled roof.

6. L'Olmo

L'Olmo
Pienza
Rp12.842.280
Rp14.208.046 total
includes taxes & fees
23 Oct - 24 Oct
L'Olmo
A large estate with multiple buildings, a swimming pool, and expansive green fields.
A dining area with brick walls, large windows, and a rustic stone ceiling. Tables are set with white tablecloths and candles.
A swimming pool with a view of a hilly landscape, surrounded by trees and grass.
A balcony with a view of a green landscape and a body of water.

7. Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
Trequanda
Rp2.916.215
Rp3.269.015 total
includes taxes & fees
26 Oct - 27 Oct
Borgo Sant'Ambrogio Resort
View all properties

Choose what matters most at family-friendly hotels in Pienza

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Family-friendly hotels with free breakfast in Pienza

A patio area with outdoor seating, potted plants, and a view of the landscape.
A well-maintained garden with a brick pathway, various potted plants, and trees.
A bedroom with a bed, a nightstand, a lamp, a chair, a table, and a window with a view of greenery.
A cozy living room with a fireplace, a dining area, and a black leather chair.

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
Rp1.976.377
Rp2.681.591 total
includes taxes & fees
7 Oct - 8 Oct
Affitacamere Maria Gabriella
Two people sitting at a round table outdoors with a scenic view of mountains in the background.
A bar area with a wooden bar counter, three orange chairs, and a variety of bottles and glasses.
A breakfast buffet with various food items and beverages.
A hotel entrance with a sign reading "Hotel Corsignano," a paved driveway, and a large terracotta pot.

Hotel Corsignano

Hotel Corsignano
Pienza
Rp3.452.331
Rp3.919.953 total
includes taxes & fees
19 Oct - 20 Oct
Hotel Corsignano
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.
A swimming pool with a water feature, surrounded by greenery and a table with chairs.
A building with a symmetrical facade, a central entrance, and a fountain in the courtyard.
A buffet with various desserts and pastries, a painting on the wall, and wooden paneling.

Hotel San Gregorio

Hotel San Gregorio
Pienza
Rp3.455.989
Rp3.923.895 total
includes taxes & fees
6 Oct - 7 Oct
Hotel San Gregorio
A villa with a swimming pool, terraced garden, and a view of distant mountains.
A stone building with a gravel pathway leading to the entrance.
A fire pit with burning logs, surrounded by stone blocks and a metal grill.
A cozy living room with a fireplace, comfortable seating, and a table set with various desserts.

Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
Rp3.583.307
Rp4.023.210 total
includes taxes & fees
27 Oct - 28 Oct
Agriturismo Il Macchione
An outdoor dining setup with various dishes on rustic wooden tables, set against a scenic backdrop of rolling hills and a sunset.
A restaurant with a rustic interior, featuring exposed brick arches, wooden beams, and a bar area in the background.
A large outdoor swimming pool with multiple sections, surrounded by lounge chairs and a modern building with a unique roof structure.
A rustic villa with traditional architecture, surrounded by olive groves and a mountainous backdrop.

Podere Spedalone

Podere Spedalone
Pienza
Rp2.797.697
Rp3.159.038 total
includes taxes & fees
25 Oct - 26 Oct
Podere Spedalone
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.
A cozy reading room with a fireplace, bookshelves, and comfortable seating.
A cozy living room with a sofa, coffee table, TV, bookshelves, and a decorative lamp.
A swimming pool with sun loungers and umbrellas, surrounded by lush greenery and a house with a tiled roof.

L'Olmo

L'Olmo
Pienza
Rp12.842.280
Rp14.208.046 total
includes taxes & fees
23 Oct - 24 Oct
L'Olmo
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.
View all properties

Top Pienza Hotel Reviews

Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"Everything was perfect the staff the hotel."
steve 1-night trip
Posted 1 day ago
Hotel Corsignano
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"
Beren 2-night trip
Posted 6 days ago
Villa di Piazzano - Small Luxury Hotel of the World
Hotel San Gregorio

Hotel San Gregorio

8/10 Good
"Quaint but modern hotel walking distance to all - good breakfast and service in hotel restaurant. Spacious rooms with air conditioning (which gets turned off when staff cleans room - call desk to turn back on), safe, and bathroom with tub- but no shower curtain- took a while to learn how to negotiate using the shower handle. Pool area is restful. Enjoyed our stay"
JANET 3-night trip
Posted 8 days ago
Hotel San Gregorio
Tenuta Santo Pietro

Tenuta Santo Pietro

10/10 Excellent
"Beautiful place to stay halfway between Pienza and Montepulciano. The food was some of the best we had during our entire time in Italy and we loved spending our afternoon by the pool with a drink."
Jenny 2-night trip
Posted 11 days ago
Tenuta Santo Pietro
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Very warm and friendly service."
Abdel 2-night trip
Posted 13 days ago
Castiglion del Bosco, A Rosewood Hotel
La Bandita Townhouse

La Bandita Townhouse

10/10 Excellent
"Fantastic venue! Loved Pienza! The Inn was beautiful and the staff extremely friendly and welcoming. We would love to go back"
Ross 1-night trip
Posted 3 weeks ago
La Bandita Townhouse

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.
What's the best family accommodation 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 options to stay with the children include Agriturismo Il Macchione and Podere Spedalone.
How many family hotels will I find in Pienza?
Expedia has 9 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.

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