A historic square with a prominent tower and statues.

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Check availability on Pienza Family-Friendly Hotels

Tonight
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

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 modern bathroom with two sinks, a shower, and a toilet.
A swimming pool with a water feature, surrounded by greenery and a table with chairs.
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.
5.965.980 ₫
6.745.088 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Hotel San Gregorio
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 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.

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.
5.151.765 ₫
5.849.452 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Hotel Corsignano
A villa with a swimming pool, terraced garden, and a view of distant mountains.
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.
A fire pit with burning logs, surrounded by stone blocks and a metal grill.

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.
5.344.609 ₫
6.001.055 ₫ total
includes taxes & fees
24 Sept - 25 Sept
Agriturismo Il Macchione
A swimming pool with a stone wall and a metal ladder, surrounded by trees and a clear sky.
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.
An outdoor dining setup with various dishes on rustic wooden tables, set against a scenic backdrop of rolling hills and a sunset.

4. Podere Spedalone

Podere Spedalone
Pienza
  • This Tuscan farm stay delights families with seasonal outdoor pool, hiking trails, and complimentary breakfast buffet each morning.
5.192.631 ₫
5.833.879 ₫ total
includes taxes & fees
11 Sept - 12 Sept
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 bedroom with a canopy bed, wooden flooring, a bedside table, and a built-in bookshelf.
A swimming pool with sun loungers and umbrellas, surrounded by lush greenery and a house with a tiled roof.

5. L'Olmo

L'Olmo
Pienza
19.212.646 ₫
21.255.896 ₫ total
includes taxes & fees
29 Aug - 30 Aug
L'Olmo
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 balcony with a view of a green landscape and a body of water.
A dining area with brick walls, large windows, and a rustic stone ceiling. Tables are set with white tablecloths and candles.

6. Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
Trequanda
4.825.265 ₫
5.398.955 ₫ total
includes taxes & fees
22 Sept - 23 Sept
Borgo Sant'Ambrogio Resort
A hanging chair in a grassy area with a view of a hilly landscape.
A stone balcony with an arched view of a rural landscape, including fields and distant hills.
A pool area with lounge chairs and umbrellas, surrounded by a field of lavender.
An arched doorway leading to a room with a large window, stone walls, and a potted plant outside.

7. Locanda Vesuna

Locanda Vesuna
Trequanda
  • Immerse in family poolside fun at this Tuscan hotel with kids' playground, game room, and seasonal rooftop swimming.
4.003.328 ₫
4.495.150 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Locanda Vesuna
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 breakfast buffet with various food items and beverages.
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

Hotel Corsignano
Pienza
5.151.765 ₫
5.849.452 ₫ total
includes taxes & fees
30 Aug - 31 Aug
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 swimming pool with a water feature, surrounded by greenery and a table with chairs.
A buffet with various desserts and pastries, a painting on the wall, and wooden paneling.

Hotel San Gregorio

Hotel San Gregorio
Pienza
5.965.980 ₫
6.745.088 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Hotel San Gregorio
A villa with a swimming pool, terraced garden, and a view of distant mountains.
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.
A fire pit with burning logs, surrounded by stone blocks and a metal grill.

Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
5.344.609 ₫
6.001.055 ₫ total
includes taxes & fees
24 Sept - 25 Sept
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 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.
A swimming pool with sun loungers and umbrellas, surrounded by lush greenery and a house with a tiled roof.

L'Olmo

L'Olmo
Pienza
19.212.646 ₫
21.255.896 ₫ total
includes taxes & fees
29 Aug - 30 Aug
L'Olmo
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.
A large outdoor swimming pool with multiple sections, surrounded by lounge chairs and a modern building with a unique roof structure.

Podere Spedalone

Podere Spedalone
Pienza
5.192.631 ₫
5.833.879 ₫ total
includes taxes & fees
11 Sept - 12 Sept
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

Tenuta Santo Pietro

Tenuta Santo Pietro

10/10 Excellent
"Such a wonderful stay. The view is breathtaking and Bertina and her team delightful. Our favorite place in Tuscany."
Annie 2-night trip
Posted 15 hours ago
Tenuta Santo Pietro
Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"We had an exceptional nice stay. I can highly recommend the Corsignano to anyone. It’s just a couple minutes walking distance from the old town … I will definitely stay here again on my next visit to Pienza"
Rene 1-night trip
Posted 2 days ago
Hotel Corsignano
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"This property was amazing from the moment we booked. Chiara was extremely helpful with looking into horseback riding and other tours for us. I made a mistake in booking and she caught it and corrected it before we even arrived. She was great. Additionally, the room was beautiful and really clean. The food was delicious and every waitstaff that we encountered was polite and attentive--it could not have been a better experience."
Amy 2-night trip
Posted 13 days ago
Castello di Velona Resort Thermal SPA & Winery
Agriturismo La Sovana

Agriturismo La Sovana

10/10 Excellent
"Beautiful stay here. Restaurant was fantastic and they prepared special dishes to meet our vegetarian needs. Buffet breakfast with fresh cappuccinos was wonderful. Room was impeccably clean with daily cleaning service. This was our second time here and we are hoping to return to this authentic Tuscany resort. You will likely not find a better place to stay at in Tuscany."
Karen 4-night trip
Posted 3 weeks ago
Agriturismo La Sovana
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Best hotel ever."
Ray 2-night trip
Posted 1 month ago
Castiglion del Bosco, A Rosewood Hotel
Hotel San Gregorio

Hotel San Gregorio

10/10 Excellent
"The hotel was beautiful maintained and a very convenient location. We stayed in a newly renovated room which was quite modern and clean with excellent spaces for clothes and toiletries which I appreciated! Our room didn’t have a view, it looked onto another building which I was a bit disappointed about. The breakfast was average, too many sweet dessert choices for my taste, but there were eggs and and a nice yogurt bar. The pool area looks nicer in the pictures than it does in person but the pool itself was nice and refreshing. They could have furnished the pool area nicer considering the area we were in! The staff were helpful and friendly, hotel was very convenient with lots of parking and it was very clean."
Traci 2-night trip
Posted 3 months ago
Hotel San Gregorio

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.
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 Palazzo Borgia. Make sure that you have lots of time for activities such as Museo Diocesano and Artemisia Gallery.

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