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Check availability on Castellina in Chianti Family-Friendly Hotels

Our top choices for Castellina in Chianti family-friendly hotels

Games room
Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (169)
The price is 2.417.866 ₫
2.783.358 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Borgo di Pietrafitta Relais
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers
Residenzia del Sogno

Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.8 out of 10, Exceptional, (14)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is 3.654.857 ₫
4.144.110 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Residenzia del Sogno
Panoramic Apartment (2) | Terrace/patio
Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
8.0 out of 10, Very good, (2)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is 3.188.181 ₫
3.692.556 ₫ total
includes taxes & fees
14 Jan - 15 Jan 2026
Casa Vacanze Squarcialupi
Front of property
Il Malaspina

Il Malaspina

Il Malaspina
4.0 star property
Historic Centre of Florence
10.0 out of 10, Exceptional, (8)
"Everything was perfect, cleanliness is top notch, staff is super helpful and friendly, Yehia is such a professional and nice guy. The hotel is super cozy and very central location!"
United States
Nadine
The price is 3.004.211 ₫
3.737.008 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Il Malaspina
Outdoor spa tub
IQ Hotel Firenze

IQ Hotel Firenze

IQ Hotel Firenze
4.0 star property
Historic Centre of Florence
9.8 out of 10, Exceptional, (1086)
"Beautiful hotel! Great location! Amazing breakfast! Amazing staff! "
Canada
Blair
The price is 2.554.950 ₫
3.242.821 ₫ total
includes taxes & fees
16 Jan - 17 Jan 2026
IQ Hotel Firenze
Garden
Orto De Medici Hotel

Orto De Medici Hotel

Orto De Medici Hotel
4.0 star property
Historic Centre of Florence
9.6 out of 10, Exceptional, (1006)
"We had a wonderful time staying and close to a lot of wonderful spots to visit. "
United States
JoAnn
The price is 3.060.297 ₫
3.798.734 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Orto De Medici Hotel
Aerial view
Hotel Athena

Hotel Athena

Hotel Athena
4.0 star property
Siena Historical Center
9.2 out of 10, Wonderful, (1008)
"Excellent hotel, very helpful staff, highly recommended "
United States
Vikram
The price is 2.319.080 ₫
2.643.671 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Hotel Athena
Property entrance
Hotel Palazzetto Rosso

Hotel Palazzetto Rosso

Hotel Palazzetto Rosso
3.0 star property
Siena City Centre
9.8 out of 10, Exceptional, (210)
"Great location and staff. "
United States
Susan
The price is 4.068.266 ₫
4.475.092 ₫ total
includes taxes & fees
15 Jan - 16 Jan 2026
Hotel Palazzetto Rosso
Breakfast meal
Palazzo Ravizza

Palazzo Ravizza

Palazzo Ravizza
4.0 star property
Siena Historical Center
9.4 out of 10, Exceptional, (746)
"We enjoyed our stay here."
United States
LAURIA
The price is 2.729.023 ₫
3.094.577 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Palazzo Ravizza
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.
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Top Castellina in Chianti Hotel Reviews

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Frequently asked questions

What's Castellina in Chianti like for family-friendly holidays?
The remote destination of Castellina in Chianti is a great choice if you've been thinking about a holiday with the children. The swimming spots and forests are just a couple of things that make this the ideal place for a family holiday. Take to the air and fly into Peretola Airport (FLR), which is located 23.2 mi (37.4 km) from the city centre.
How many family hotels can I expect to find in Castellina in Chianti?
Expedia has 11 family-friendly hotels and other accommodation options in Castellina in Chianti.
When's the best time to book a family-friendly holiday in Castellina in Chianti?
The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Castellina in Chianti is 935 mm.
What's there to see and do with your family in Castellina in Chianti?
While you are visiting Castellina in Chianti, you and the family may want to explore some interesting spots such as Archaeological Museum of Chianti, Walls of Monteriggioni and Borgo di Vescine - Tenute di Castelvecchi. Make sure that you have lots of time for activities such as Museo del Cristallo di Colle di Val d'Elsa and Siena State Archives.