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 stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

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

17 Nov - 18 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 555 total

includes taxes & fees

30 Nov - 1 Dec

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 2,038 total

includes taxes & fees

18 Nov - 19 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

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

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

Casa Vacanze Squarcialupi

Castellina in Chianti

8/10 Good

Jeffrey

Albergo Il Colombaio

Castellina in Chianti

10/10 Excellent

Christine

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 courtyard with wicker furniture, a building with multiple windows and arches, and well-maintained greenery.

Palazzo Ravizza

Siena Historical Center

10/10 Excellent

Anonymous traveler

A historic building complex with multiple structures, including a large central building with arches and smaller surrounding buildings.

Hotel Athena

Siena Historical Center

10/10 Excellent

Jenn

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

Hotel Chiusarelli

Siena City Centre

10/10 Excellent

Lorenzo

A historic square with a central fountain, surrounded by stone buildings with arched windows and a prominent tower.

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 building with a staircase, potted plants, and a garden area.

Art Hotel Villa Agape - Place of Charme

Oltrarno

10/10 Excellent

Amazing in every way. The beauty of waking around is unlike any other. When we got there after a long day of traveling we had just missed the lunchtime to eat, and when went to shower the handle broke off- this is not a complaint. First they extended lunch without being asked and fixed the shower within minutes. From there on everything was amazing. Take time to eat the incredible breakfast in the garden, watch the breathtaking sunset in the back it’s incredible. Alessio- does it all he was...

John

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

The entrance to Hotel Spadaï Firenze with a modern design, including a reception desk and a chandelier.

Hotel Spadai

Historic Centre of Florence

10/10 Excellent

Richard

A lobby with ornate columns, a reception desk, and a staircase.

Bernini Palace

Historic Centre of Florence

10/10 Excellent

Sarah

A modern interior with a glass elevator, a seating area with orange cushions, and a bookshelf filled with books.

Hotel Milu Florence

Historic Centre of Florence

10/10 Excellent

What a fantastic experience at Milu! To start, the staff was friendly and made us feel at home right away. Our room was clean and quiet, with the most amazing shower! We enjoyed the breakfast on the patio and found it to be a very satisfying way to start the day. The hotel maintained a relaxed feel while still being vibrant - colorful, modern art and design to enjoy while relaxing with a cup of tea from the open library. We would definitely stay again, thanks Milu for a great experience!

Kelly

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

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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