TOP Family Friendly Hotels in Pienza for 2026 - 𝗙𝗿𝗲𝗲 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 on Select Hotels | Expedia Singapore

A historic square with a prominent tower and statues.

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Check availability on Pienza Family friendly Hotels

Tonight

10 Oct - 11 Oct

Tomorrow

11 Oct - 12 Oct

Next weekend

16 Oct - 18 Oct

In two weeks

23 Oct - 25 Oct

Our top choices for Pienza family-friendly hotels

A living room with a sofa, armchairs, a coffee table, a cabinet, and a lamp.

A historic town with a prominent church, a courtyard with a swimming pool, and terraced buildings.

A bathroom with a toilet, bidet, sink, and shower.

A buffet setup with various food items and condiments.

1. Relais Cloister Pienza

Pienza

S$189

includes taxes & fees

25 Oct - 26 Oct

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

A hotel room with a bed, a desk with a computer, a TV, a wardrobe, and a mirror.

A buffet with various desserts and pastries, a painting on the wall, and wooden paneling.

A modern bathroom with two sinks, a shower, and a toilet.

2. Hotel San Gregorio

Pienza

Tuscan residence welcomes families with outdoor pool, hot tubs, and optional babysitting services just steps from Palazzo Piccolomini.

S$191

includes taxes & fees

8 Nov - 9 Nov

Two people sitting at a round table outdoors with a scenic view of mountains in the background.

A breakfast buffet with various food items and beverages.

A bar area with a wooden bar counter, three orange chairs, and a variety of bottles and glasses.

A hotel entrance with a sign reading "Hotel Corsignano," a paved driveway, and a large terracotta pot.

3. Hotel Corsignano

Pienza

Families find paradise with babysitting services, bicycle rentals, and two hot tubs just steps from Pienza's historic treasures.

S$192

includes taxes & fees

10 Nov - 11 Nov

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 cozy living room with a fireplace, comfortable seating, and a table set with various desserts.

A stone building with a tiled roof, surrounded by a grassy area and flowering plants.

4. Agriturismo Il Macchione

Pienza

Splash into family fun at this Pienza retreat where kids adore the playground while parents unwind poolside at the winery.

S$191

includes taxes & fees

5 Nov - 6 Nov

A room with a green cabinet, a mirror, a sink, and a television.

A cozy dining area with a table set for four, surrounded by wooden chairs and a patterned tablecloth.

A cozy living room with a fireplace, a dining area, and a black leather chair.

A bedroom with a bed, a nightstand, a lamp, a chair, a table, and a window with a view of greenery.

5. Affitacamere Maria Gabriella

Pienza

S$178

includes taxes & fees

3 Nov - 4 Nov

An outdoor dining area with wooden tables and benches, stone walls, and greenery.

A stone corridor with a vaulted ceiling and an arched doorway at the end.

A modern living room with a white sofa, a coffee table, and a bookshelf.

A courtyard with a stone building, arched openings, and a covered seating area.

6. La Bandita Townhouse

Pienza

S$612

includes taxes & fees

3 Nov - 4 Nov

A cozy room with a fireplace, two armchairs, and a table.

A building with a stone facade, surrounded by trees and shrubs, and illuminated by warm lights.

An outdoor dining area with tables set for two, surrounded by chairs, and large windows offering a view of the greenery outside.

A cozy room with a pool table, comfortable seating, and a large arched window offering a view of the outdoors.

7. Tenuta Santo Pietro

Pienza

S$342

includes taxes & fees

12 Oct - 13 Oct

A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

A cozy dining area with a table, chairs, a flower centerpiece, and a window with curtains.

A room with a view of a historic town, featuring stone buildings and a clear sky.

A bedroom with a four-poster bed, a wooden chest, a desk with a chair, and a window with blue curtains.

8. PienzaLettings Suites

Pienza

S$114

includes taxes & fees

2 Nov - 3 Nov

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 living room with a sofa, armchairs, a coffee table, a cabinet, and a lamp.

A buffet setup with various food items and condiments.

A poolside area with lounge chairs and umbrellas, a stone wall, and a clear sky.

A room with a herringbone floor, a bed, a sofa, a desk, and a view through a window.

Relais Cloister Pienza

Pienza

S$189

includes taxes & fees

25 Oct - 26 Oct

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

A hotel room with a bed, a desk with a computer, a TV, a wardrobe, and a mirror.

A buffet with various desserts and pastries, a painting on the wall, and wooden paneling.

A building with a symmetrical facade, a central entrance, and a fountain in the courtyard.

Hotel San Gregorio

Pienza

S$191

includes taxes & fees

8 Nov - 9 Nov

Two people sitting at a round table outdoors with a scenic view of mountains in the background.

A breakfast buffet with various food items and beverages.

A bar area with a wooden bar counter, three orange chairs, and a variety of bottles and glasses.

A hotel entrance with a sign reading "Hotel Corsignano," a paved driveway, and a large terracotta pot.

Hotel Corsignano

Pienza

S$192

includes taxes & fees

10 Nov - 11 Nov

A patio area with outdoor seating, potted plants, and a view of the landscape.

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 well-maintained garden with a brick pathway, various potted plants, and trees.

Affitacamere Maria Gabriella

Pienza

S$178

includes taxes & fees

3 Nov - 4 Nov

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 cozy living room with a fireplace, comfortable seating, and a table set with various desserts.

A stone building with a tiled roof, surrounded by a grassy area and flowering plants.

Agriturismo Il Macchione

Pienza

S$191

includes taxes & fees

5 Nov - 6 Nov

A cozy room with a fireplace, two armchairs, and a table.

A building with a stone facade, surrounded by trees and shrubs, and illuminated by warm lights.

An outdoor dining area with tables set for two, surrounded by chairs, and large windows offering a view of the greenery outside.

A cozy room with a pool table, comfortable seating, and a large arched window offering a view of the outdoors.

Tenuta Santo Pietro

Pienza

S$342

includes taxes & fees

12 Oct - 13 Oct

An outdoor dining area with wooden tables and benches, stone walls, and greenery.

A stone corridor with a vaulted ceiling and an arched doorway at the end.

A modern living room with a white sofa, a coffee table, and a bookshelf.

A courtyard with a stone building, arched openings, and a covered seating area.

La Bandita Townhouse

Pienza

S$612

includes taxes & fees

3 Nov - 4 Nov

A modern interior with a stone wall, wooden paneling, and a television.

A dining area with tables and chairs, a buffet with various food items, and large windows offering a view of trees.

A rectangular swimming pool with clear water, surrounded by a brick patio.

A villa with a tower, a swimming pool, and a well-maintained garden.

Hotel Rutiliano Centro Benessere

Pienza

S$280

includes taxes & fees

15 Oct - 16 Oct

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 rustic stone building with a tower, surrounded by lush greenery and a vegetable garden.

A large outdoor swimming pool with multiple sections, surrounded by lounge chairs and a modern building with a unique roof structure.

Podere Spedalone

Pienza

S$222

includes taxes & fees

30 Oct - 31 Oct

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 swimming pool with sun loungers and umbrellas, surrounded by lush greenery and a house with a tiled roof.

A cozy reading room with a fireplace, bookshelves, and comfortable seating.

A bedroom with a canopy bed, wooden flooring, a bedside table, and a built-in bookshelf.

L'Olmo

Pienza

S$637

includes taxes & fees

2 Nov - 3 Nov

View all properties

Family-friendly hotels with pools in Pienza

A living room with a sofa, armchairs, a coffee table, a cabinet, and a lamp.

A buffet setup with various food items and condiments.

A poolside area with lounge chairs and umbrellas, a stone wall, and a clear sky.

A room with a herringbone floor, a bed, a sofa, a desk, and a view through a window.

Relais Cloister Pienza

Pienza

S$189

includes taxes & fees

25 Oct - 26 Oct

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

A hotel room with a bed, a desk with a computer, a TV, a wardrobe, and a mirror.

A buffet with various desserts and pastries, a painting on the wall, and wooden paneling.

A building with a symmetrical facade, a central entrance, and a fountain in the courtyard.

Hotel San Gregorio

Pienza

S$191

includes taxes & fees

8 Nov - 9 Nov

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 cozy living room with a fireplace, comfortable seating, and a table set with various desserts.

A stone building with a tiled roof, surrounded by a grassy area and flowering plants.

Agriturismo Il Macchione

Pienza

S$191

includes taxes & fees

5 Nov - 6 Nov

A cozy room with a fireplace, two armchairs, and a table.

A building with a stone facade, surrounded by trees and shrubs, and illuminated by warm lights.

An outdoor dining area with tables set for two, surrounded by chairs, and large windows offering a view of the greenery outside.

A cozy room with a pool table, comfortable seating, and a large arched window offering a view of the outdoors.

Tenuta Santo Pietro

Pienza

S$342

includes taxes & fees

12 Oct - 13 Oct

A modern interior with a stone wall, wooden paneling, and a television.

A dining area with tables and chairs, a buffet with various food items, and large windows offering a view of trees.

A rectangular swimming pool with clear water, surrounded by a brick patio.

A villa with a tower, a swimming pool, and a well-maintained garden.

Hotel Rutiliano Centro Benessere

Pienza

S$280

includes taxes & fees

15 Oct - 16 Oct

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 rustic stone building with a tower, surrounded by lush greenery and a vegetable garden.

A large outdoor swimming pool with multiple sections, surrounded by lounge chairs and a modern building with a unique roof structure.

Podere Spedalone

Pienza

S$222

includes taxes & fees

30 Oct - 31 Oct

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 swimming pool with sun loungers and umbrellas, surrounded by lush greenery and a house with a tiled roof.

A cozy reading room with a fireplace, bookshelves, and comfortable seating.

A bedroom with a canopy bed, wooden flooring, a bedside table, and a built-in bookshelf.

L'Olmo

Pienza

S$637

includes taxes & fees

2 Nov - 3 Nov

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 San Gregorio

Hotel San Gregorio

8/10 Good

"Great location, clean room and communal space. We were disappointed that we were given a room with jacuzzi but no shower and refrigerator was broken. Overall a nice experience"

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Nice and quiet excellent hospitality"

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"Stunning property; a real representation of Tuscany with the long driveway of tall trees; staff was amazing; food was excellent; gardens, picturesque! We would highly recommend! Overall amazing !!!"

Palazzuolo

Palazzuolo

10/10 Excellent

"Excellent room, good location, the staff is very gentle, the breakfast is good"

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano

10/10 Excellent

"Our stay for our honeymoon was amazing. We loved our room and we were upgraded to a suite because they had it available. All the staff were kind and helpful. They carried our luggage up two flights of stairs to our room, helped make reservations, called taxis for us, etc. The property was beautiful, maintained nicely, and was very quiet. Really have no complaints. To note it is outside of city Centre of Siena so you will need taxis back and forth to the city for meals etc. which can get quite pricey so just plan ahead. Our room could’ve been cleaned a little better in between each day but overall it was still very clean. We would definitely stay there again!!"

La Bandita Townhouse

La Bandita Townhouse

10/10 Excellent

"Great 12 room boutique hotel in the heart of Pienza."

Hotel Villa Ricci

Hotel Villa Ricci

10/10 Excellent

"Personal, muy amable y educado, muy cálida, recepción, lindo hotel. Lo aconsejo para quienes quieran visitar la toscana y sobretodo Montepulciano."

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Amazing views. Relaxing stay! A very romantic hotel, though I was surprised by the number of families there; given its location and amenities, I had assumed it was geared towards couples. That isn't a negative comment, though—it was simply a case of my own mistaken perception."

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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