Chianti Region Family Friendly Hotels, Tuscany: Chianti Region Hotel Guide

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Our top choices for Chianti Region 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 stone building with a courtyard, a covered seating area, and a small bell tower.

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.

€85

includes taxes & fees

25 Oct - 26 Oct

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.

A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

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

2. La Certosa di Pontignano

Castelnuovo Berardenga

€97

includes taxes & fees

25 Oct - 26 Oct

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 wooden door, outdoor seating, and a pergola with vines.

A stone building with a window and a light fixture.

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

3. Agriturismo San Sano

Gaiole in Chianti

Sip Tuscan wines by the pool while kids explore the playground and garden at this family-friendly farmhouse retreat.

€75

includes taxes & fees

18 Oct - 19 Oct

A sauna room with wooden benches, a stone basin, and a window.

A poolside area with outdoor seating and umbrellas, overlooking a scenic landscape.

A table with breakfast items, a clear view of the countryside, and a white umbrella.

A woman sitting on a chair in a room with a staircase, a wall-mounted light, and a tiled floor.

4. Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

A perfect family escape awaits in Italy, complete with outdoor pools, spa amenities, and nearby castle adventures for the whole family.

€80

includes taxes & fees

1 Nov - 2 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.

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

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

5. Castello di Tornano Wine Resort

Gaiole in Chianti

€147

includes taxes & fees

26 Oct - 27 Oct

A pool with a view of a lush valley and distant buildings.

A courtyard with stone buildings, arched doorways, and potted plants.

A terraced vineyard with stone walls and a stone pathway leading to a seating area with metal chairs and tables.

A garden with neatly trimmed hedges, a gravel path, and a stone barrel.

6. Castello Vicchiomaggio

Greve in Chianti

€167

includes taxes & fees

27 Oct - 28 Oct

An outdoor dining area with a pool, potted plants, and umbrellas.

A villa with a swimming pool, outdoor seating, and a garden.

An outdoor dining area with a table set for two, overlooking a pool and vineyard.

A restaurant with a table set for two, overlooking a scenic landscape.

7. Relais Vignale & Spa

Radda in Chianti

Family paradise at historic wine country hotel with rooftop pool and arcade room for all-ages entertainment.

€188

includes taxes & fees

26 Oct - 27 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.

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

A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.

8. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

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

€99

includes taxes & fees

22 Oct - 23 Oct

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

Breakfast included

Pool

All-inclusive

4 stars

5 stars

Family-friendly hotels with free breakfast in Chianti Region

A pool with a view of a lush valley and distant buildings.

A courtyard with stone buildings, arched doorways, and potted plants.

A terraced vineyard with stone walls and a stone pathway leading to a seating area with metal chairs and tables.

A garden with neatly trimmed hedges, a gravel path, and a stone barrel.

Castello Vicchiomaggio

Greve in Chianti

€167

includes taxes & fees

27 Oct - 28 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 dining area with a stone wall, wooden beams, and a table set for four with wine glasses and plates.

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

Borgo di Pietrafitta Relais

Castellina in Chianti

€85

includes taxes & fees

25 Oct - 26 Oct

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.

A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

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

La Certosa di Pontignano

Castelnuovo Berardenga

€97

includes taxes & fees

25 Oct - 26 Oct

An outdoor dining area with a pool, potted plants, and umbrellas.

A villa with a swimming pool, outdoor seating, and a garden.

An outdoor dining area with a table set for two, overlooking a pool and vineyard.

A restaurant with a table set for two, overlooking a scenic landscape.

Relais Vignale & Spa

Radda in Chianti

€188

includes taxes & fees

26 Oct - 27 Oct

A poolside area with outdoor seating and umbrellas, overlooking a scenic landscape.

A table with breakfast items, a clear view of the countryside, and a white umbrella.

A bedroom with a large bed, a view of a green landscape through a sliding door, and a potted plant on the windowsill.

A pathway lined with wooden fences and benches, leading to a covered seating area with tables and chairs.

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

€80

includes taxes & fees

1 Nov - 2 Nov

A couple dining at an outdoor table with a view of the countryside.

A spacious room with high arched ceilings, a wooden dining table, chairs, and a bookshelf.

A narrow street with buildings on either side, a flag, and a bench.

A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

€120

includes taxes & fees

2 Nov - 3 Nov

A spacious living area with a large window, a sofa, a green armchair, and a patterned armchair.

A kitchen area with a marble countertop, a stone wall, and a sign reading "Cooking Class".

A stone building with a tower, a glass structure, and outdoor seating.

A swimming pool with clear water, surrounded by lounge chairs and trees.

Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

€113

includes taxes & fees

1 Nov - 2 Nov

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

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

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

Belvedere di San Leonino

Castellina in Chianti

€126

includes taxes & fees

15 Oct - 16 Oct

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 wooden door, outdoor seating, and a pergola with vines.

A stone building with a window and a light fixture.

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

Agriturismo San Sano

Gaiole in Chianti

€75

includes taxes & fees

18 Oct - 19 Oct

A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.

A rustic outdoor setting with a stone building, round tables, and outdoor seating.

A modern living room with a white sofa, armchairs, and a coffee table.

Chapter Chianti, a Member of Design Hotels

Cavriglia

€270

includes taxes & fees

6 Oct - 7 Oct

View all properties

Family-friendly hotels with pools in Chianti Region

A pool with a view of a lush valley and distant buildings.

A courtyard with stone buildings, arched doorways, and potted plants.

A terraced vineyard with stone walls and a stone pathway leading to a seating area with metal chairs and tables.

A garden with neatly trimmed hedges, a gravel path, and a stone barrel.

Castello Vicchiomaggio

Greve in Chianti

€167

includes taxes & fees

27 Oct - 28 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 dining area with a stone wall, wooden beams, and a table set for four with wine glasses and plates.

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

Borgo di Pietrafitta Relais

Castellina in Chianti

€85

includes taxes & fees

25 Oct - 26 Oct

An outdoor dining area with a pool, potted plants, and umbrellas.

A villa with a swimming pool, outdoor seating, and a garden.

An outdoor dining area with a table set for two, overlooking a pool and vineyard.

A restaurant with a table set for two, overlooking a scenic landscape.

Relais Vignale & Spa

Radda in Chianti

€188

includes taxes & fees

26 Oct - 27 Oct

A person sitting by a swimming pool with a stone building in the background.

A sunset scene with a person holding a child, benches, and umbrellas in a park setting.

A person relaxing on a sun lounger by a pool with a table beside them holding a drink and a bowl.

A stone building with a wooden door and an arched window.

Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa

€135

includes taxes & fees

24 Oct - 25 Oct

A poolside area with outdoor seating and umbrellas, overlooking a scenic landscape.

A table with breakfast items, a clear view of the countryside, and a white umbrella.

A bedroom with a large bed, a view of a green landscape through a sliding door, and a potted plant on the windowsill.

A pathway lined with wooden fences and benches, leading to a covered seating area with tables and chairs.

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

€80

includes taxes & fees

1 Nov - 2 Nov

A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.

A rustic outdoor setting with a stone building, round tables, and outdoor seating.

A modern living room with a white sofa, armchairs, and a coffee table.

Chapter Chianti, a Member of Design Hotels

Cavriglia

€270

includes taxes & fees

6 Oct - 7 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 stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

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

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

Belvedere di San Leonino

Castellina in Chianti

€126

includes taxes & fees

15 Oct - 16 Oct

A couple dining at an outdoor table with a view of the countryside.

A spacious room with high arched ceilings, a wooden dining table, chairs, and a bookshelf.

A narrow street with buildings on either side, a flag, and a bench.

A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

€120

includes taxes & fees

2 Nov - 3 Nov

A wicker chair, a lantern, and a vase of flowers on a balcony with a mountain view.

A rustic stone building with a tiled roof, surrounded by lush greenery and white flowers.

A bedroom with a large bed, a bedside table, and a chair.

A pool area with a view of a hilly landscape.

Borgo Del Cabreo

Greve in Chianti

€309

includes taxes & fees

11 Oct - 12 Oct

An indoor courtyard with stone flooring, arched columns, and tables set up for dining.

A modern spa area with a wooden sauna, a glass-enclosed shower, and a marble-floored pool.

A modern reception area with a stone counter, a sign for SPA VILLA CASAGRANDE, and a staircase leading to a glass door.

A historic building with a stone facade, arched entrance, and a wooden balcony.

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

€111

includes taxes & fees

1 Nov - 2 Nov

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 Chianti Region Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"From the moment we checked in, This place was a Gem. From the friendly and helpful staff to the beautiful grounds, we were so impressed. Its hard to put into words how wonderful this Hotel is. The food, and drinks were incredible. We also celebrated my wife's birthday at this resort and they did a very special dinner for us to enjoy. Along with Campaign and a personalized Birthday dessert. Special thanks to Noamie (hope i got that right). She was absolutely wonderful. I could go on forever about this Resort. So easy to explore the region while calling this a comfortable landing spot. Can't thank the team enough for a wonderful stay."

Palagina la Dimora

Palagina la Dimora

8/10 Good

"Was staying locally for business but the pools open too late for an early swim, which was the plan...so a bit of a disappointment, upside is that you walk to Sting's pizza place :-)"

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

8/10 Good

"Under renovation so it could have been better"

Relais Vignale & Spa

Relais Vignale & Spa

10/10 Excellent

"In a convenient location."

Villa Le Barone

Villa Le Barone

10/10 Excellent

"Charming place in Tuscany! Everything was absolutely perfect. We highly suggest to dine at the villa, it was exceptional. Breakfast was delicious as well."

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village

10/10 Excellent

"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."

Villa Il Palagio

Villa Il Palagio

10/10 Excellent

"The check in went great and the property is amazingly managed, a beautiful villa in the hills of Tuscany. It felt magic just walking to it, I would absolutely recommend renting a car if you want to go into Florence often."

Hotel Villa Campomaggio

Hotel Villa Campomaggio

10/10 Excellent

"Great hotel"

Park Hotel Chianti

Park Hotel Chianti

10/10 Excellent

"The staff are very helpful and kind."

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