A stone building with a clock tower, steps leading up to it, and people walking around.

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Check availability on Castellina in Chianti Family Hotels

This weekend
Aug 7 - Aug 9
Next weekend
Aug 14 - Aug 16

Our top choices for Castellina in Chianti family-friendly hotels

Game room

1. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (184 reviews)
  • cleanliness
    Create memories at this countryside retreat with a dedicated playground, outdoor pool, and family adventures for all ages.
The price is ₩191,403
₩217,187 total
includes taxes & fees
Aug 27 - Aug 28
Borgo di Pietrafitta Relais
Gift shop

2. Belvedere di San Leonino

Belvedere di San Leonino
4.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (190 reviews)
  • cleanliness
    Tuscan family adventures await at this hillside haven with a sparkling outdoor pool, wine tastings, and kid-friendly activities.
The price is ₩183,313
₩211,599 total
includes taxes & fees
Aug 23 - Aug 24
Belvedere di San Leonino
Lounge

3. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
The price is ₩131,830
₩151,650 total
includes taxes & fees
Aug 4 - Aug 5
Mariani Bed & Breakfast
Panoramic Apartment (2) | Terrace/patio

4. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
8.8 out of 10, Excellent, (3 reviews)
The price is ₩187,338
₩216,027 total
includes taxes & fees
Aug 30 - Aug 31
Casa Vacanze Squarcialupi
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

5. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
The price is ₩176,471
₩200,762 total
includes taxes & fees
Aug 30 - Aug 31
Residenzia del Sogno
Outdoor banquet area

6. Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany
5.0 star property
Casole d'Elsa
9.6 out of 10, Exceptional, (83 reviews)
  • cleanliness
    Family-friendly adventures in the Tuscan countryside await at this historic estate with pools, tennis, and luxurious spa escapes.
The price is ₩2,721,058
₩2,996,482 total
includes taxes & fees
Aug 14 - Aug 15
Castello di Casole, A Belmond Hotel, Tuscany
Aerial view

7. Hotel Athena

Hotel Athena
4.0 star property
Siena Historical Center
9.2 out of 10, Wonderful, (1,002 reviews)
The price is ₩232,982
₩264,573 total
includes taxes & fees
Aug 21 - Aug 22
Hotel Athena
Breakfast meal

8. Palazzo Ravizza

Palazzo Ravizza
4.0 star property
Siena Historical Center
9.4 out of 10, Exceptional, (837 reviews)
The price is ₩230,776
₩262,151 total
includes taxes & fees
Aug 24 - Aug 25
Palazzo Ravizza
Rooftop terrace

9. Villa del Sole Siena

Villa del Sole Siena
Siena City Centre
9.8 out of 10, Exceptional, (672 reviews)
  • cleanliness
    Kids can explore historic Siena from this inviting hotel that offers cribs, continental breakfast, and proximity to Piazza del Campo.
The price is ₩280,584
₩316,937 total
includes taxes & fees
Aug 26 - Aug 27
Villa del Sole Siena
2 bars/lounges

10. Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione
5.0 star property
Siena City Centre
9.2 out of 10, Wonderful, (622 reviews)
  • cleanliness
    Family adventures await at this Siena luxury hotel with in-room babysitting and cultural attractions steps away.
The price is ₩512,836
₩580,713 total
includes taxes & fees
Aug 26 - Aug 27
Grand Hotel Continental Siena – Starhotels Collezione
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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Choose what matters most at family-friendly hotels in Castellina in Chianti

Pool
Breakfast included

Top Castellina in Chianti Hotel Reviews

Palazzo Montebello

Palazzo Montebello

10/10 Excellent
"Very convenient location Quiet inside and outside. Comfortable and helpful staff.."
Pallavi 2-night trip
Posted 8 hours ago
Palazzo Montebello

Frequently asked questions

What's Castellina in Chianti like for family-friendly vacations?
The remote destination of Castellina in Chianti is a great choice if you've been thinking about a vacation with the kids. The swimming spots and forests are just a few things that make this the ideal place for a family vacation. Take to the air and fly into Florence Airport, Peretola (FLR), which is located 23.2 mi (37.4 km) from the city center.
What's the best hotel for a family vacation in Castellina in Chianti?
Belvedere di San Leonino is a hotel with an outdoor pool and a restaurant, and it's a top choice on Expedia for families. Borgo di Pietrafitta Relais is another good option for your family trip.
How many family-friendly hotels will I find in Castellina in Chianti?
Expedia has 5 family-friendly hotels and other accommodations in Castellina in Chianti.
When's the best time to book a family-friendly vacation in Castellina in Chianti?
The hottest months are usually August and July with an average temp of 72°F, while the coldest months are January and February with an average of 44°F. Average annual precipitation for Castellina in Chianti is 37 inches.
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 might want to check out some interesting spots such as Archaeological Museum of Chianti, Walls of Monteriggioni, and Chianti Observatory. Make sure you have lots of time for activities like Borgo di Vescine - Tenute di Castelvecchi and Museo del Cristallo di Colle di Val d'Elsa.