Family friendly Hotels, Pienza Tuscany | Expedia

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Check availability on Pienza Family friendly Hotels

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Oct 16 - Oct 18

Our top choices for Pienza family-friendly hotels

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

A hotel room with a bed, bedside lamps, a desk with a coffee maker, and a window with curtains.

1. Relais Cloister Pienza

Pienza

P8,051

P9,278 total

includes taxes & fees

Oct 25 - Oct 26

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.

2. Hotel San Gregorio

Pienza

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

P8,768

P10,066 total

includes taxes & fees

Nov 6 - Nov 7

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

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

A patio area with wicker furniture, a glass table, and a pool in the background.

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

3. Hotel Corsignano

Pienza

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

P9,029

P10,353 total

includes taxes & fees

Nov 4 - Nov 5

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

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

A modern interior with a white sofa, wooden coffee table, and bookshelves filled with books.

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

4. La Bandita Townhouse

Pienza

P24,441

P27,166 total

includes taxes & fees

Nov 3 - Nov 4

A villa with a swimming pool, terraced garden, and a view of distant mountains.

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

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

A fire pit with burning logs, surrounded by stone blocks and a metal grill.

5. Agriturismo Il Macchione

Pienza

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

P8,895

P10,066 total

includes taxes & fees

Nov 5 - Nov 6

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

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.

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

6. Hotel Rutiliano Centro Benessere

Pienza

P12,234

P13,738 total

includes taxes & fees

Oct 8 - Oct 9

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

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

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

A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and greenery.

7. Tenuta Santo Pietro

Pienza

P16,102

P17,994 total

includes taxes & fees

Oct 8 - Oct 9

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

A wooden door with a sign, a staircase with blue steps, and a metal handrail.

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

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

8. PienzaLettings Suites

Pienza

P5,070

P5,858 total

includes taxes & fees

Nov 2 - Nov 3

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

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

A hotel room with a bed, bedside lamps, a desk with a coffee maker, and a window with curtains.

Relais Cloister Pienza

Pienza

P8,051

P9,278 total

includes taxes & fees

Oct 25 - Oct 26

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

Pienza

P8,768

P10,066 total

includes taxes & fees

Nov 6 - Nov 7

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

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

A patio area with wicker furniture, a glass table, and a pool in the background.

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

Hotel Corsignano

Pienza

P9,029

P10,353 total

includes taxes & fees

Nov 4 - Nov 5

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 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.

Affitacamere Maria Gabriella

Pienza

P6,815

P9,246 total

includes taxes & fees

Oct 7 - Oct 8

A villa with a swimming pool, terraced garden, and a view of distant mountains.

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

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

A fire pit with burning logs, surrounded by stone blocks and a metal grill.

Agriturismo Il Macchione

Pienza

P8,895

P10,066 total

includes taxes & fees

Nov 5 - Nov 6

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

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

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

A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and greenery.

Tenuta Santo Pietro

Pienza

P16,102

P17,994 total

includes taxes & fees

Oct 8 - Oct 9

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

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

A modern interior with a white sofa, wooden coffee table, and bookshelves filled with books.

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

La Bandita Townhouse

Pienza

P24,441

P27,166 total

includes taxes & fees

Nov 3 - Nov 4

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

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.

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

Hotel Rutiliano Centro Benessere

Pienza

P12,234

P13,738 total

includes taxes & fees

Oct 8 - Oct 9

An outdoor dining setup with various dishes on rustic wooden tables, set against a scenic backdrop of rolling hills and a sunset.

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

A restaurant with a rustic interior, featuring exposed brick arches, wooden beams, and a bar area in the background.

A rustic villa with traditional architecture, surrounded by olive groves and a mountainous backdrop.

Podere Spedalone

Pienza

P9,642

P10,888 total

includes taxes & fees

Oct 25 - Oct 26

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 living room with a sofa, coffee table, TV, bookshelves, and a decorative lamp.

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

L'Olmo

Pienza

P28,115

P31,208 total

includes taxes & fees

Nov 2 - Nov 3

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

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

A hotel room with a bed, bedside lamps, a desk with a coffee maker, and a window with curtains.

Relais Cloister Pienza

Pienza

P8,051

P9,278 total

includes taxes & fees

Oct 25 - Oct 26

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

Pienza

P8,768

P10,066 total

includes taxes & fees

Nov 6 - Nov 7

A villa with a swimming pool, terraced garden, and a view of distant mountains.

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

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

A fire pit with burning logs, surrounded by stone blocks and a metal grill.

Agriturismo Il Macchione

Pienza

P8,895

P10,066 total

includes taxes & fees

Nov 5 - Nov 6

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

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

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

A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and greenery.

Tenuta Santo Pietro

Pienza

P16,102

P17,994 total

includes taxes & fees

Oct 8 - Oct 9

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

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.

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

Hotel Rutiliano Centro Benessere

Pienza

P12,234

P13,738 total

includes taxes & fees

Oct 8 - Oct 9

An outdoor dining setup with various dishes on rustic wooden tables, set against a scenic backdrop of rolling hills and a sunset.

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

A restaurant with a rustic interior, featuring exposed brick arches, wooden beams, and a bar area in the background.

A rustic villa with traditional architecture, surrounded by olive groves and a mountainous backdrop.

Podere Spedalone

Pienza

P9,642

P10,888 total

includes taxes & fees

Oct 25 - Oct 26

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 living room with a sofa, coffee table, TV, bookshelves, and a decorative lamp.

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

L'Olmo

Pienza

P28,115

P31,208 total

includes taxes & fees

Nov 2 - Nov 3

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

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 !!!"

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."

Hotel Corsignano

Hotel Corsignano

10/10 Excellent

"Everything was perfect the staff the hotel."

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 Agriturismo Il Macchione and Podere Spedalone.

How many family-friendly hotels are there in Pienza?

Expedia has 9 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.

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