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

A stone castle with battlements overlooking a lush valley with vineyards.

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Check availability on Gaiole in Chianti Family friendly Hotels

Tonight

11 Oct - 12 Oct

Tomorrow

12 Oct - 13 Oct

Next weekend

16 Oct - 18 Oct

In two weeks

23 Oct - 25 Oct

Our top choices for Gaiole in Chianti family-friendly hotels

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

A stone building with a garden, tall trees, and a clear blue sky.

A restaurant with stone walls and a high ceiling, featuring tables set for dining.

An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.

1. Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

S$479

includes taxes & fees

30 Oct - 31 Oct

A stone building with a tiled roof, surrounded by a well-maintained garden and a view of rolling hills.

A stone building with a tiled roof, a stone pathway, and a well-maintained lawn.

A stone building with a tiled roof, surrounded by a well-maintained garden with potted plants and a pathway.

A pool with a view of a mountainous landscape and a village in the background.

2. Cavarchino B&B

Gaiole in Chianti

S$220

includes taxes & fees

11 Nov - 12 Nov

A swimming pool with a view of a historic building surrounded by olive trees.

An outdoor café with tables and chairs, surrounded by stone walls and greenery.

A stone building with a circular tower, a gravel pathway, and a metal archway leading to a wooden door.

An aerial view of a castle with a courtyard, surrounded by vineyards and dense trees.

3. Castello di Meleto

Gaiole in Chianti

S$198

includes taxes & fees

12 Oct - 13 Oct

A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.

A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.

An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

4. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

Tuscan retreat offers poolside cabanas, kid-supervised swimming, and free bicycle rentals for memorable family adventures.

S$139

includes taxes & fees

22 Oct - 23 Oct

A stone building with a yellow sign reading "b&b erioico".

A modern dining area with a wooden table, glass vases, and a staircase with glass railings.

A stone building with a balcony, a bike rental sign, and a chair in the foreground.

A bathroom with a glass shower enclosure, a toilet, a sink with a wooden vanity, and a window with curtains.

5. L' Eroico

Gaiole in Chianti

S$197

includes taxes & fees

2 Nov - 3 Nov

A dining table with a meal, wine glasses, and a pepper mill.

A stone building with a tower, surrounded by people dining at tables with candles.

An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.

A stone archway leading to a window with a view of tall trees and a distant landscape.

6. Castello di Tornano Wine Resort

Gaiole in Chianti

S$226

includes taxes & fees

25 Oct - 26 Oct

A traditional stone building with a garden featuring geometric hedges and potted plants.

A breakfast setting with a table set for two, including plates of fruit, a cup of coffee, a glass of juice, and a bottle of wine.

A formal garden with geometric hedges, a stone building with green shutters, and a staircase leading to a covered area.

A view of a garden with neatly trimmed hedges and a central water feature.

7. Badia a Coltibuono

Gaiole in Chianti

S$225

includes taxes & fees

22 Oct - 23 Oct

A pool with a statue in the center, surrounded by trees and hills.

Room

A spacious bedroom with a large bed, a wooden chair, and a view of the outdoors through an open door.

A breakfast buffet with various meats, cheeses, and bread, set against a stone wall backdrop.

8. Borgo Casa al Vento

Gaiole in Chianti

S$248

includes taxes & fees

1 Nov - 2 Nov

View all properties

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

Pool

Breakfast included

All-inclusive

4 stars

5 stars

Family-friendly hotels with pools in Gaiole in Chianti

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

A stone building with a garden, tall trees, and a clear blue sky.

A restaurant with stone walls and a high ceiling, featuring tables set for dining.

An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.

Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

S$479

includes taxes & fees

30 Oct - 31 Oct

A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.

A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.

An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

S$139

includes taxes & fees

22 Oct - 23 Oct

A swimming pool with a view of a historic building surrounded by olive trees.

An outdoor café with tables and chairs, surrounded by stone walls and greenery.

A stone building with a circular tower, a gravel pathway, and a metal archway leading to a wooden door.

An aerial view of a castle with a courtyard, surrounded by vineyards and dense trees.

Castello di Meleto

Gaiole in Chianti

S$198

includes taxes & fees

12 Oct - 13 Oct

A stone building with a tiled roof, surrounded by a well-maintained garden and a view of rolling hills.

A stone building with a tiled roof, a stone pathway, and a well-maintained lawn.

A stone building with a tiled roof, surrounded by a well-maintained garden with potted plants and a pathway.

A pool with a view of a mountainous landscape and a village in the background.

Cavarchino B&B

Gaiole in Chianti

S$220

includes taxes & fees

11 Nov - 12 Nov

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

A stone building with a tower, surrounded by people dining at tables with candles.

An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.

A stone archway leading to a window with a view of tall trees and a distant landscape.

Castello di Tornano Wine Resort

Gaiole in Chianti

S$226

includes taxes & fees

25 Oct - 26 Oct

A traditional stone building with a garden featuring geometric hedges and potted plants.

A breakfast setting with a table set for two, including plates of fruit, a cup of coffee, a glass of juice, and a bottle of wine.

A formal garden with geometric hedges, a stone building with green shutters, and a staircase leading to a covered area.

A view of a garden with neatly trimmed hedges and a central water feature.

Badia a Coltibuono

Gaiole in Chianti

S$225

includes taxes & fees

22 Oct - 23 Oct

A pool with a statue in the center, surrounded by trees and hills.

Room

A spacious bedroom with a large bed, a wooden chair, and a view of the outdoors through an open door.

A breakfast buffet with various meats, cheeses, and bread, set against a stone wall backdrop.

Borgo Casa al Vento

Gaiole in Chianti

S$248

includes taxes & fees

1 Nov - 2 Nov

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

A stone building with a window and a light fixture.

A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.

A pool surrounded by lush greenery and vineyards, with a stone building in the background.

Agriturismo San Sano

Gaiole in Chianti

S$106

includes taxes & fees

2 Nov - 3 Nov

A stone building with a garden in front.

A woman sitting by a pool with lounge chairs and umbrellas in the background.

A view through a window with a metal grid, featuring a stone building, greenery, and a clear sky.

A courtyard with stone walls, potted plants, and a metal fence.

Borgo Argenina

Gaiole in Chianti

S$251

includes taxes & fees

15 Oct - 16 Oct

A swimming pool with a colorful inflatable ring and a water fountain.

A pathway leading to a swimming pool surrounded by dense greenery and trees.

A neatly made bed with a purple pillow, two bedside tables with lamps, and a wooden door.

A rustic villa with a gravel driveway, surrounded by olive trees and a clear blue sky.

Agriturismo Crocino in Chianti

Gaiole in Chianti

S$203

includes taxes & fees

11 Nov - 12 Nov

View all properties

Family-friendly hotels with free breakfast in Gaiole in Chianti

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

A stone building with a garden, tall trees, and a clear blue sky.

A restaurant with stone walls and a high ceiling, featuring tables set for dining.

An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.

Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

S$479

includes taxes & fees

30 Oct - 31 Oct

A swimming pool with a view of a historic building surrounded by olive trees.

An outdoor café with tables and chairs, surrounded by stone walls and greenery.

A stone building with a circular tower, a gravel pathway, and a metal archway leading to a wooden door.

An aerial view of a castle with a courtyard, surrounded by vineyards and dense trees.

Castello di Meleto

Gaiole in Chianti

S$198

includes taxes & fees

12 Oct - 13 Oct

A stone building with a tiled roof, surrounded by a well-maintained garden and a view of rolling hills.

A stone building with a tiled roof, a stone pathway, and a well-maintained lawn.

A stone building with a tiled roof, surrounded by a well-maintained garden with potted plants and a pathway.

A pool with a view of a mountainous landscape and a village in the background.

Cavarchino B&B

Gaiole in Chianti

S$220

includes taxes & fees

11 Nov - 12 Nov

A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.

A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.

An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

S$139

includes taxes & fees

22 Oct - 23 Oct

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

A stone building with a tower, surrounded by people dining at tables with candles.

An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.

A stone archway leading to a window with a view of tall trees and a distant landscape.

Castello di Tornano Wine Resort

Gaiole in Chianti

S$226

includes taxes & fees

25 Oct - 26 Oct

A traditional stone building with a garden featuring geometric hedges and potted plants.

A breakfast setting with a table set for two, including plates of fruit, a cup of coffee, a glass of juice, and a bottle of wine.

A formal garden with geometric hedges, a stone building with green shutters, and a staircase leading to a covered area.

A view of a garden with neatly trimmed hedges and a central water feature.

Badia a Coltibuono

Gaiole in Chianti

S$225

includes taxes & fees

22 Oct - 23 Oct

A stone building with a yellow sign reading "b&b erioico".

A hotel room with neatly folded towels on the bed, a wooden headboard, and a green pendant light.

A modern dining area with a wooden table, glass vases, and a staircase with glass railings.

An aerial view of a town with a central square, surrounding buildings, and vineyards.

L' Eroico

Gaiole in Chianti

S$197

includes taxes & fees

2 Nov - 3 Nov

A pool with a statue in the center, surrounded by trees and hills.

Room

A spacious bedroom with a large bed, a wooden chair, and a view of the outdoors through an open door.

A breakfast buffet with various meats, cheeses, and bread, set against a stone wall backdrop.

Borgo Casa al Vento

Gaiole in Chianti

S$248

includes taxes & fees

1 Nov - 2 Nov

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

A stone building with a window and a light fixture.

A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.

A pool surrounded by lush greenery and vineyards, with a stone building in the background.

Agriturismo San Sano

Gaiole in Chianti

S$106

includes taxes & fees

2 Nov - 3 Nov

A stone building with a garden in front.

A woman sitting by a pool with lounge chairs and umbrellas in the background.

A view through a window with a metal grid, featuring a stone building, greenery, and a clear sky.

A courtyard with stone walls, potted plants, and a metal fence.

Borgo Argenina

Gaiole in Chianti

S$251

includes taxes & fees

15 Oct - 16 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 Gaiole in Chianti Hotel Reviews

Villa Olmi Firenze

Villa Olmi Firenze

10/10 Excellent

"Everything is unique and sweet and this property from the front desk staff to breakfast to the villa and all the way to the garden. It’s a gorgeous place and we will return for sure!!"

Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

10/10 Excellent

"Modern Hotel, A/C, great breakfast, and Taxis available non stop!"

Hu Firenze Camping In Town

Hu Firenze Camping In Town

10/10 Excellent

"Loved the place. Our cabin was perfect & it’s right on a bus line into town."

Hotel Athena

Hotel Athena

10/10 Excellent

"Lovely hotel in Siena. Well located for exploring on foot with the main Palazzo and the Duomo no more than 15 minutes away. Really enjoyed the rooftop patio!"

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Beautiful hotel and very helpful staff. Excellent location in the heart of Siena. Disappointed with our hotel room. Not up to our expectations."

Borgo Vescine

Borgo Vescine

10/10 Excellent

"The staff was amazing and incredibly kind."

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

Hotel Mulino di Firenze, WorldHotels Crafted

Hotel Mulino di Firenze, WorldHotels Crafted

10/10 Excellent

"From the moment we arrived to the moment we left the staff were fantastic. Lapo, at the front desk, was extremely helpful in making last minute arrangements for anything we needed. The entire staff from the porters, bar tenders, cleaning staff and managers were friendly and accommodating. The property was picturesque and absolutely stunning. We wish we would have stayed more days just to enjoy the property itself. If you're having an afternoon drink on the patio bar or enjoying a scrumptious evening meal in the restaurant you will not be disappointed."

Poderi Arcangelo

Poderi Arcangelo

10/10 Excellent

"Beautiful property, nice and helping staff. We enjoy our stay ."

Frequently asked questions

What's Gaiole in Chianti like for family-friendly holidays?

You may want to consider the remote destination of Gaiole in Chianti if you've been thinking about a trip for the whole family. The swimming spots, castle and famous monuments are just a few things that make this an attractive family holiday destination. Arrange a flight into Peretola Airport (FLR), which is located 25.9 mi (41.7 km) from the city centre.

What's the best family accommodation in Gaiole in Chianti?

Agriturismo San Sano is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families. Other good options to stay with the children include Ultimo Mulino Wellness Country Hotel and Agriturismo Crocino in Chianti.

How many family hotels will I be able to find in Gaiole in Chianti?

Expedia has 6 family-friendly hotels and other accommodation options in Gaiole in Chianti.

When's the best time to book a family-friendly holiday in Gaiole 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 Gaiole in Chianti is 935 mm.

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

While you and your family are visiting Gaiole in Chianti, you may want to explore some child-friendly attractions such as Gaiole in Chianti Stadium, Borgo di Vescine - Tenute di Castelvecchi and Villa a Sesta Polo Club. Make sure that you have lots of time for activities such as Chianti Observatory and Siena Circuit.

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