A historic square with a prominent tower and statues.

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Check availability on Pienza Family-Friendly Hotels

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Pienza family-friendly hotels

Two people sitting at a round table outdoors with a scenic view of mountains in the background.
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.
A hotel entrance with a sign reading "Hotel Corsignano," a paved driveway, and a large terracotta pot.

1. Hotel Corsignano

Hotel Corsignano
Pienza
  • Families find paradise with babysitting services, bicycle rentals, and two hot tubs just steps from Pienza's historic treasures.
Rp3.533.238
Rp4.008.207 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 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.
A swimming pool with a water feature, surrounded by greenery and a table with chairs.

2. 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.
Rp2.580.499
Rp2.960.234 total
includes taxes & fees
28 Oct - 29 Oct
Hotel San Gregorio
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 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.

3. 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.
Rp3.503.460
Rp3.935.351 total
includes taxes & fees
27 Oct - 28 Oct
Agriturismo Il Macchione
A room with a green cabinet, a mirror, a sink, and a television.
A patio area with outdoor seating, potted plants, and a view of the landscape.
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.

4. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
Rp1.965.675
Rp2.667.070 total
includes taxes & fees
7 Oct - 8 Oct
Affitacamere Maria Gabriella
A swimming pool with a stone wall and a metal ladder, surrounded by trees and a clear sky.
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.
A restaurant with a rustic interior, featuring exposed brick arches, wooden beams, and a bar area in the background.

5. Podere Spedalone

Podere Spedalone
Pienza
  • This Tuscan farm stay delights families with seasonal outdoor pool, hiking trails, and complimentary breakfast buffet each morning.
Rp2.781.400
Rp3.140.637 total
includes taxes & fees
30 Oct - 31 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 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 bedroom with a canopy bed, wooden flooring, a bedside table, and a built-in bookshelf.

6. L'Olmo

L'Olmo
Pienza
Rp8.920.644
Rp9.893.805 total
includes taxes & fees
1 Nov - 2 Nov
L'Olmo
A cave-like interior with a central hot spring, rocky formations, and a staircase leading to a higher level.
A glass-enclosed pool area with multiple levels and seating, surrounded by trees and stone walls.
A bathroom with a glass shower enclosure, a white sink, and a mirror.
An indoor rock formation with a hot tub and a waterfall feature.

7. Wellness Center Casanova Hotel e SPA

Wellness Center Casanova Hotel e SPA
San Quirico d'Orcia
  • A Tuscan family retreat with tennis courts, pool, and outdoor activities for adventurous kids of all ages.
Rp3.738.499
Rp4.193.936 total
includes taxes & fees
6 Oct - 7 Oct
Wellness Center Casanova Hotel e SPA
A large estate with multiple buildings, a swimming pool, and expansive green fields.
A swimming pool with a view of a hilly landscape, surrounded by trees and grass.
A restaurant with brick arches, white tablecloths, and floral centerpieces.
A dining area with brick walls, large windows, and a rustic stone ceiling. Tables are set with white tablecloths and candles.

8. Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
Trequanda
Rp3.017.072
Rp3.379.939 total
includes taxes & fees
13 Oct - 14 Oct
Borgo Sant'Ambrogio Resort
A hanging chair in a grassy area with a view of a hilly landscape.
A stone courtyard with a fountain, outdoor seating, and a view of the countryside.
A pool area with lounge chairs and umbrellas, surrounded by a field of lavender.
A stone balcony with an arched view of a rural landscape, including fields and distant hills.

9. Locanda Vesuna

Locanda Vesuna
Trequanda
  • Immerse in family poolside fun at this Tuscan hotel with kids' playground, game room, and seasonal rooftop swimming.
Rp3.706.658
Rp4.138.484 total
includes taxes & fees
13 Oct - 14 Oct
Locanda Vesuna
A rustic interior with exposed brick walls, a stone archway, and wooden furniture.
A bathroom with a bathtub, a large wall-mounted painting, a cushioned bench, and a rustic wooden floor.
A rustic building with a tiled roof overlooking a rural landscape with fields and a distant mountain.
A stone-walled bedroom with a bed, two bedside lamps, a wooden bench, and a window with curtains.

10. Locanda In Tuscany

Locanda In Tuscany
Castiglione d'Orcia
Rp4.036.243
Rp4.521.413 total
includes taxes & fees
27 Oct - 28 Oct
Locanda In Tuscany
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

Two people sitting at a round table outdoors with a scenic view of mountains in the background.
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.
A hotel entrance with a sign reading "Hotel Corsignano," a paved driveway, and a large terracotta pot.

Hotel Corsignano

Hotel Corsignano
Pienza
Rp3.533.238
Rp4.008.207 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 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.
A swimming pool with a water feature, surrounded by greenery and a table with chairs.

Hotel San Gregorio

Hotel San Gregorio
Pienza
Rp2.580.499
Rp2.960.234 total
includes taxes & fees
28 Oct - 29 Oct
Hotel San Gregorio
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 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
Rp3.503.460
Rp3.935.351 total
includes taxes & fees
27 Oct - 28 Oct
Agriturismo Il Macchione
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 bedroom with a canopy bed, wooden flooring, a bedside table, and a built-in bookshelf.

L'Olmo

L'Olmo
Pienza
Rp8.920.644
Rp9.893.805 total
includes taxes & fees
1 Nov - 2 Nov
L'Olmo
A patio area with outdoor seating, potted plants, and a view of the landscape.
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.
A cozy dining area with a table set for four, surrounded by wooden chairs and a patterned tablecloth.

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
Rp1.965.675
Rp2.667.070 total
includes taxes & fees
7 Oct - 8 Oct
Affitacamere Maria Gabriella
An outdoor dining setup with various dishes on rustic wooden tables, set against a scenic backdrop of rolling hills and a sunset.
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.
A restaurant with a rustic interior, featuring exposed brick arches, wooden beams, and a bar area in the background.

Podere Spedalone

Podere Spedalone
Pienza
Rp2.781.400
Rp3.140.637 total
includes taxes & fees
30 Oct - 31 Oct
Podere Spedalone
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
"All good"
Leo 4-night trip
Posted 1 hour ago
Hotel San Gregorio
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Castiglion del Bosco is truly exquisite, the perfect way to experience Tuscany in luxury while still feeling completely surrounded by nature. The property is impeccable, from the beautiful gardens and grounds to the elegant rooms. Everything feels authentically Italian, refined and incredibly well maintained. The service is exceptional and very personalized. The staff genuinely goes out of their way to make you feel welcome. General Manager Nicola Migheli even greeted us personally upon arrival, which was a lovely touch. We also saw him regularly walking the property with his team, and it was clear how hands-on he is with every detail. One thing to know is that getting in and out requires about 40 minutes on a bumpy dirt road. It wasn’t terrible, but worth mentioning if you plan to explore frequently. That said, this is a hotel you don’t need to leave. It’s a beautiful place to slow down, relax and enjoy Tuscany in a truly special setting. We absolutely loved our stay!"
Carole 5-night trip
Posted 7 hours ago
Castiglion del Bosco, A Rosewood Hotel
La Bandita Townhouse

La Bandita Townhouse

10/10 Excellent
"Great 12 room boutique hotel in the heart of Pienza."
Robert 1-night trip
Posted 3 days ago
La Bandita Townhouse
Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"Everything was perfect the staff the hotel."
steve 1-night trip
Posted 6 days 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 10 days ago
Villa di Piazzano - Small Luxury Hotel of the World

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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