TOP Family Friendly Hotels in Castellina in Chianti for 2026 - 𝗙𝗿𝗲𝗲 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 on Select Hotels | Expedia Singapore

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Check availability on Castellina in Chianti Family friendly Hotels

Tonight

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10 Oct - 11 Oct

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Next weekend

16 Oct - 18 Oct

Our top choices for Castellina in Chianti family-friendly hotels

A small wooden cabin surrounded by a circular gravel path, with a playground in the background.

A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.

A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and lush greenery, overlooking a valley.

A dining area with a stone wall, wooden beams, and a table set for four with wine glasses and plates.

1. Borgo di Pietrafitta Relais

Castellina in Chianti

Create memories at this countryside retreat with a dedicated playground, outdoor pool, and family adventures for all ages.

S$130

includes taxes & fees

25 Oct - 26 Oct

A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.

A rustic interior with a brick archway, wooden beams, a bar area, and potted plants.

A stone building with a wooden bench outside.

A clear blue pool with lounge chairs and a stone building in the background.

2. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

S$156

includes taxes & fees

12 Oct - 13 Oct

A spa area with a stone ceiling, a large bathtub, and a seating area.

A garden with a gravel path leading to a white metal table and chairs, surrounded by red roses and a large terracotta pot.

A historic building with a courtyard, stone arches, and a tiled roof.

A bedroom with a bed, bedside tables, a sofa, a window with curtains, and a wall with a painting.

3. Palazzo Squarcialupi

Castellina in Chianti

S$288

includes taxes & fees

18 Oct - 19 Oct

A stately building with a grand entrance, multiple arches, and a well-lit facade.

A room with a wooden floor, a bathtub, a chair, a bed, and large windows offering a view of the countryside.

A swimming pool with lounge chairs and an umbrella, surrounded by trees.

A restaurant with stone walls, wooden furniture, and a wine cellar.

4. Fattoria di Vegi

Castellina in Chianti

S$386

includes taxes & fees

20 Oct - 21 Oct

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.

A person relaxing in a hot tub with a view of a building and trees in the background.

A rustic stone building with a garden in front.

A poolside area with lounge chairs and a view of the night sky.

5. 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.

S$165

includes taxes & fees

15 Oct - 16 Oct

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

A bedroom with a bed, bedside tables, a chair, and a window with curtains.

A room with a dining table set for two, a TV on a wooden stand, and a view of a vineyard through a glass door.

A balcony with a table set for two, overlooking a vineyard and distant hills.

6. Casa Vacanze Squarcialupi

Castellina in Chianti

S$169

includes taxes & fees

6 Nov - 7 Nov

A long table set for dining in a tunnel with wine barrels on one side.

A sculpture of two figures in a garden with a windmill in the background.

A spacious bedroom with a large bed, a desk, and a chair. There is a painting on the wall and a window with curtains.

A castle-like building with a swimming pool and a well-maintained garden.

7. Agriturismo Villa Godenano - Pool & Suites

Castellina in Chianti

S$240

includes taxes & fees

26 Oct - 27 Oct

A historic building with a stone facade, multiple windows with shutters, and a well-maintained garden with potted plants and flowers.

A spacious living room with striped sofas, a coffee table, and a chandelier.

A bench in a park with a lamp post and a building in the background.

A hallway with a wooden altar, benches, and a carpet with a floral pattern.

8. Villa Casalecchi Country Hotel

Castellina in Chianti

Outdoor pool paradise in Chianti where families relax under Tuscan sun, with cots available and horseback riding nearby.

S$217

includes taxes & fees

11 Oct - 12 Oct

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

Pool

Breakfast included

All-inclusive

4 stars

5 stars

Family-friendly hotels with pools in Castellina in Chianti

A spa area with a stone ceiling, a large bathtub, and a seating area.

A garden with a gravel path leading to a white metal table and chairs, surrounded by red roses and a large terracotta pot.

A historic building with a courtyard, stone arches, and a tiled roof.

A bedroom with a bed, bedside tables, a sofa, a window with curtains, and a wall with a painting.

Palazzo Squarcialupi

Castellina in Chianti

S$288

includes taxes & fees

18 Oct - 19 Oct

A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.

A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and lush greenery, overlooking a valley.

A stone building with a courtyard, a covered seating area, and a small bell tower.

A cozy living room with a stone fireplace, striped sofas, and a coffee table.

Borgo di Pietrafitta Relais

Castellina in Chianti

S$130

includes taxes & fees

25 Oct - 26 Oct

A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.

A rustic interior with a brick archway, wooden beams, a bar area, and potted plants.

A stone building with a wooden bench outside.

A clear blue pool with lounge chairs and a stone building in the background.

Hotel Colle Etrusco Salivolpi

Castellina in Chianti

S$156

includes taxes & fees

12 Oct - 13 Oct

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.

A person relaxing in a hot tub with a view of a building and trees in the background.

A rustic stone building with a garden in front.

A poolside area with lounge chairs and a view of the night sky.

Belvedere di San Leonino

Castellina in Chianti

S$165

includes taxes & fees

15 Oct - 16 Oct

A long table set for dining in a tunnel with wine barrels on one side.

A sculpture of two figures in a garden with a windmill in the background.

A spacious bedroom with a large bed, a desk, and a chair. There is a painting on the wall and a window with curtains.

A castle-like building with a swimming pool and a well-maintained garden.

Agriturismo Villa Godenano - Pool & Suites

Castellina in Chianti

S$240

includes taxes & fees

26 Oct - 27 Oct

A stately building with a grand entrance, multiple arches, and a well-lit facade.

A well-decorated living room with a sofa, a coffee table, and a vase with flowers.

A swimming pool with lounge chairs and an umbrella, surrounded by trees.

A restaurant with stone walls, wooden furniture, and a wine cellar.

Fattoria di Vegi

Castellina in Chianti

S$386

includes taxes & fees

20 Oct - 21 Oct

A historic building with a stone facade, multiple windows with shutters, and a well-maintained garden with potted plants and flowers.

A spacious living room with striped sofas, a coffee table, and a chandelier.

A bench in a park with a lamp post and a building in the background.

A hallway with a wooden altar, benches, and a carpet with a floral pattern.

Villa Casalecchi Country Hotel

Castellina in Chianti

S$217

includes taxes & fees

11 Oct - 12 Oct

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

A stone-walled room with tables set for dining, a staircase, and a lamp.

A stone building with a large arched doorway, a bench, and a potted plant outside.

A stone staircase leading to a wooden balcony with a view of a mountainous landscape.

Albergo Il Colombaio

Castellina in Chianti

S$209

includes taxes & fees

11 Oct - 12 Oct

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

A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

A view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.

A building with arched windows, a courtyard with a pond, and a metal fence.

Hotel Casafrassi

Castellina in Chianti

S$93

includes taxes & fees

18 Oct - 19 Oct

A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

A stone building with a wooden door and a balcony with flower planters.

An outdoor dining area with tables and chairs, a pergola structure, and potted plants.

A pool area with a view of vineyards and hills.

Riserva di Fizzano Residence

Castellina in Chianti

S$278

includes taxes & fees

19 Oct - 20 Oct

View all properties

Family-friendly hotels with free breakfast in Castellina in Chianti

A spa area with a stone ceiling, a large bathtub, and a seating area.

A garden with a gravel path leading to a white metal table and chairs, surrounded by red roses and a large terracotta pot.

A historic building with a courtyard, stone arches, and a tiled roof.

A bedroom with a bed, bedside tables, a sofa, a window with curtains, and a wall with a painting.

Palazzo Squarcialupi

Castellina in Chianti

S$288

includes taxes & fees

18 Oct - 19 Oct

A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.

A rustic interior with a brick archway, wooden beams, a bar area, and potted plants.

A stone building with a wooden bench outside.

A clear blue pool with lounge chairs and a stone building in the background.

Hotel Colle Etrusco Salivolpi

Castellina in Chianti

S$156

includes taxes & fees

12 Oct - 13 Oct

A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.

A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and lush greenery, overlooking a valley.

A stone building with a courtyard, a covered seating area, and a small bell tower.

A cozy living room with a stone fireplace, striped sofas, and a coffee table.

Borgo di Pietrafitta Relais

Castellina in Chianti

S$130

includes taxes & fees

25 Oct - 26 Oct

A long table set for dining in a tunnel with wine barrels on one side.

A sculpture of two figures in a garden with a windmill in the background.

A spacious bedroom with a large bed, a desk, and a chair. There is a painting on the wall and a window with curtains.

A castle-like building with a swimming pool and a well-maintained garden.

Agriturismo Villa Godenano - Pool & Suites

Castellina in Chianti

S$240

includes taxes & fees

26 Oct - 27 Oct

A stately building with a grand entrance, multiple arches, and a well-lit facade.

A well-decorated living room with a sofa, a coffee table, and a vase with flowers.

A swimming pool with lounge chairs and an umbrella, surrounded by trees.

A restaurant with stone walls, wooden furniture, and a wine cellar.

Fattoria di Vegi

Castellina in Chianti

S$386

includes taxes & fees

20 Oct - 21 Oct

A historic building with a stone facade, multiple windows with shutters, and a well-maintained garden with potted plants and flowers.

A spacious living room with striped sofas, a coffee table, and a chandelier.

A bench in a park with a lamp post and a building in the background.

A hallway with a wooden altar, benches, and a carpet with a floral pattern.

Villa Casalecchi Country Hotel

Castellina in Chianti

S$217

includes taxes & fees

11 Oct - 12 Oct

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

A stone-walled room with tables set for dining, a staircase, and a lamp.

A stone building with a large arched doorway, a bench, and a potted plant outside.

A stone staircase leading to a wooden balcony with a view of a mountainous landscape.

Albergo Il Colombaio

Castellina in Chianti

S$209

includes taxes & fees

11 Oct - 12 Oct

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.

A person relaxing in a hot tub with a view of a building and trees in the background.

A rustic stone building with a garden in front.

A poolside area with lounge chairs and a view of the night sky.

Belvedere di San Leonino

Castellina in Chianti

S$165

includes taxes & fees

15 Oct - 16 Oct

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

A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

A view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.

A building with arched windows, a courtyard with a pond, and a metal fence.

Hotel Casafrassi

Castellina in Chianti

S$93

includes taxes & fees

18 Oct - 19 Oct

A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

A stone building with a wooden door and a balcony with flower planters.

An outdoor dining area with tables and chairs, a pergola structure, and potted plants.

A pool area with a view of vineyards and hills.

Riserva di Fizzano Residence

Castellina in Chianti

S$278

includes taxes & fees

19 Oct - 20 Oct

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 Castellina in Chianti Hotel Reviews

Hotel Albani Firenze

Hotel Albani Firenze

10/10 Excellent

"Beautiful hotel! Great location close to the market, attractions and train station. Breakfast was excellent with a good variety of items and great service."

Plus Florence - Hostel

Plus Florence - Hostel

10/10 Excellent

"Buena ubicacion, habitacion limpia. Desayuno bueno, delicioso y barato. El personal del hotel muy amable y siempre dispuesto a ayudar. Definotivamente lo recomiendo 100%.🌻"

Hu Firenze Camping In Town

Hu Firenze Camping In Town

10/10 Excellent

"Très agréable, offrant les avantages du camping et de la ville"

Villa Neroli

Villa Neroli

10/10 Excellent

"Great and affordable hotel outside Florence so we could have a pool to cool down in. Lovely restaurant on site, didn’t explore food options in walking distance. Helpful staff who explained bus routes etc into Florence Bus route with various app really easy to follow and buy ticket. Took about 20 mins to get into centre. We travelled in August and it was late 30’s temp wise each day so was a relief to come back to the hotel each afternoon to cool off in air con and pool. The family room we had was two enormous Rooms very spacious. Second room had space for three kids. Wonderful hotel would recommend and return if I was ever going back to Florence"

Grand Hotel Cavour

Grand Hotel Cavour

10/10 Excellent

"Staff was friendly and accommodating! Rooms were very clean and SPACIOUS! Would definitely return!"

Art Hotel Villa Agape

Art Hotel Villa Agape

10/10 Excellent

"Loved this hotel. We stayed here for one night before flying home and it was beautiful, well maintained and food was good."

Grand Hotel Baglioni

Grand Hotel Baglioni

10/10 Excellent

"Great hotel within walking distance of the historic centre of Florence. Helpful and knowledgeable staff. Amazing views from the rooftop bar/ restaurant. Thank you"

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.

What's the best family accommodation 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 choice for your child-friendly holiday.

How many family hotels can I expect to find in Castellina in Chianti?

Expedia has 5 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 Chianti Observatory. Make sure that you have lots of time for activities such as Borgo di Vescine - Tenute di Castelvecchi and Archeodromo di Poggibonsi.

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