A group of people standing on a balcony with a tiled roof and a window.

Find Family Hotels in Castellina in Chianti

Dates

November 2026

December 2026

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Our top choices for Castellina in Chianti family-friendly hotels

A stone building with an arched entrance, a wooden door, and a small balcony with a railing.

1. Albergo Il Colombaio

Castellina in Chianti

AED 614 total

includes taxes & fees

10 Dec - 11 Dec

A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

2. Belvedere di San Leonino

Castellina in Chianti

Tuscan family adventures await at this hillside haven with a sparkling outdoor pool, wine tastings, and kid-friendly activities.

AED 456 total

includes taxes & fees

12 Nov - 13 Nov

A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

3. Casa Vacanze Squarcialupi

Castellina in Chianti

AED 486 total

includes taxes & fees

11 Nov - 12 Nov

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

4. Agriturismo La Ferrozzola

Castellina in Chianti

AED 532 total

includes taxes & fees

10 Nov - 11 Nov

A stone-paved entrance with a grill, potted plants, and a door leading to an interior space.

5. Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

Castellina in Chianti

AED 522 total

includes taxes & fees

11 Nov - 12 Nov

A brick building with a garden, a metal fence, and a clear sky.

6. Casa Marisa in Castellina in Chianti

Castellina in Chianti

AED 1,105 total

includes taxes & fees

11 Nov - 12 Nov

A bedroom with a bed, bedside tables, a dresser, a window with curtains, and wall-mounted lights.

7. Apartment 'La Casa Della Gina' with Wi-Fi

Castellina in Chianti

AED 1,989 total

includes taxes & fees

15 Nov - 16 Nov

A rustic outdoor dining area with a stone wall, wooden furniture, and potted plants.

8. La Misura, cottage with garden and swimming pool on the hills of Chianti

Castellina in Chianti

An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

9. Hotel Casafrassi

Castellina in Chianti

AED 266 total

includes taxes & fees

18 Nov - 19 Nov

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

10. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

AED 309 total

includes taxes & fees

10 Nov - 11 Nov

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Choose what matters most at family-friendly hotels in Castellina in Chianti

Pool

Breakfast included

Family-friendly hotels with pools in Castellina in Chianti

Hotel Casafrassi

Castellina in Chianti

AED 266 total

includes taxes & fees

18 Nov - 19 Nov

La Misura, cottage with garden and swimming pool on the hills of Chianti

Castellina in Chianti

View all properties

Top Castellina in Chianti Hotel Reviews

Belvedere di San Leonino

Castellina in Chianti

10/10 Excellent

Oh wow, perfect vacation and a real Tuscany atmosphere, the hotel is a magical old yet perfectly renovated property, the room was amazingly clean and equipped with everything we needed, the pool was open until 8pm and it’s never crowded, very peaceful area, almost like a fantasy movie, breakfast was great, especially the cheese , local pastries and coffee , the staff was lovely, very friendly and helpful, but the real deal was DINNER , I cannot say enough about the food and wine they make,...

Lior

Albergo Il Colombaio

Castellina in Chianti

10/10 Excellent

Christine

Casa Vacanze Squarcialupi

Castellina in Chianti

8/10 Good

Jeffrey

Hotel Casafrassi

Castellina in Chianti

10/10 Excellent

Rita

La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

10/10 Excellent

Jeffrey

A terrace with wicker chairs and a table set for breakfast, overlooking a historic town with terracotta buildings and cypress trees.

Villa del Sole Siena

Siena City Centre

10/10 Excellent

Linna

A table with breakfast items and a wicker chair, overlooking a scenic landscape.

Palazzo Ravizza

Siena Historical Center

10/10 Excellent

Anonymous traveler

A lobby with a marble floor, a chandelier, a reception desk, and large green plants.

Hotel Chiusarelli

Siena City Centre

10/10 Excellent

Lorenzo

An outdoor dining area with tables and chairs, surrounded by a brick wall and greenery.

Hotel Athena

Siena Historical Center

10/10 Excellent

Jenn

An outdoor café with tables and chairs, a stone building with arched windows, and a sign for 'Albergo Cisterna'.

La Cisterna

San Gimignano City Centre

10/10 Excellent

Old hotel in an old mountain top town. Given the limitations of this environment the Cisterna is a great little hotel that met all of our needs .The Cisterna is located in Cisterna Square in town close to sights, dining and a valley view walkway. The views to the valley from the rooms is amazing. The rooms are a good size and are modernized and comfortable. The staff is great (friendly and helpful). Many choices for dining close by (in the square) but others will require some minor hills and...

David

A rooftop terrace with a table set for dining, candles, and a vase of flowers, overlooking a historic cityscape with notable architecture.

Hotel Santa Maria Novella

Historic Centre of Florence

10/10 Excellent

Nick

A pool area with two seating areas, each with a covered table and chairs, surrounded by a pool.

Hotel Horto Convento

Historic Centre of Florence

10/10 Excellent

Jassiel

A view from a window overlooking a busy square with historic buildings, a carousel, and a café table with a book and cup.

Hotel Pendini

Historic Centre of Florence

10/10 Excellent

William

A garden pathway with white flowers and a glass structure overhead.

Hotel Orto de’ Medici

Historic Centre of Florence

10/10 Excellent

Christopher

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 Archeodromo di Poggibonsi.

Find Family Hotels in Castellina in Chianti

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Castellina in Chianti family-friendly hotels

1. Albergo Il Colombaio

2. Belvedere di San Leonino

3. Casa Vacanze Squarcialupi

4. Agriturismo La Ferrozzola

5. Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

6. Casa Marisa in Castellina in Chianti

7. Apartment 'La Casa Della Gina' with Wi-Fi

8. La Misura, cottage with garden and swimming pool on the hills of Chianti

9. Hotel Casafrassi

10. La Certosa di Pontignano - Place of Charme

Choose what matters most at family-friendly hotels in Castellina in Chianti

Family-friendly hotels with pools in Castellina in Chianti

Hotel Casafrassi

Top Castellina in Chianti Hotel Reviews

Belvedere di San Leonino

10/10 Excellent

Frequently Asked Questions

What's Castellina in Chianti like for family-friendly vacations?

What's the best hotel for a family vacation in Castellina in Chianti?

How many family-friendly hotels will I find in Castellina in Chianti?

When’s the best time to book a family-friendly vacation in Castellina in Chianti?

What's there to see and do with your family in Castellina in Chianti?

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