TOP Chianti Region Hotels with FREE Breakfast for 2026 - 𝗙𝗿𝗲𝗲 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 on Select Hotels | Expedia Singapore

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Check availability on Chianti Region Hotels with free breakfast

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16 Oct - 18 Oct

Our top choices for Chianti Region hotels with free breakfast

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.

An interior corridor with arches, columns, and a brick wall.

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

1. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Wake up to local Tuscan cuisine at this idyllic historic B&B surrounded by serene gardens.

S$148

includes taxes & fees

2 Nov - 3 Nov

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.

2. Borgo di Pietrafitta Relais

Castellina in Chianti

S$130

includes taxes & fees

27 Oct - 28 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 person relaxing in a hot tub with a view of a building and trees in the background.

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

3. Belvedere di San Leonino

Castellina in Chianti

S$167

includes taxes & fees

10 Oct - 11 Oct

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

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

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

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

4. Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

Daily champagne breakfast in a luxurious tuscan setting with panoramic countryside views.

S$133

includes taxes & fees

8 Nov - 9 Nov

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

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

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

A historic stone building with a large arched window and a small balcony.

5. Castello di Tornano Wine Resort

Gaiole in Chianti

S$225

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

6. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

S$164

includes taxes & fees

1 Nov - 2 Nov

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

A spacious living room with a high ceiling, large windows with diamond-patterned blinds, a sofa set, a coffee table, and a painting on the wall.

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

A pool area with a view of a hilly landscape.

7. Borgo Del Cabreo

Greve in Chianti

S$371

includes taxes & fees

11 Oct - 12 Oct

A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

A dining area with a table set for two, featuring wine bottles and bread.

A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.

A courtyard with stone buildings, outdoor tables set for dining, and a gravel ground.

8. Castello La Leccia

Castellina in Chianti

A tranquil morning begins with complimentary local cuisine breakfast at this charming Tuscan hotel, where regional flavours start each day.

S$288

includes taxes & fees

3 Nov - 4 Nov

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Choose what matters most at hotels with breakfast available in Chianti Region

Pool

4 stars

5 stars

Wifi included

Family-friendly

Hotels with free breakfast and pools in Chianti Region

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

27 Oct - 28 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 woman sitting on a chair in a room with a staircase, a wall-mounted light, and a tiled floor.

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

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

S$108

includes taxes & fees

8 Nov - 9 Nov

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.

An indoor dining area with stone walls, tables set with tablecloths and chairs, and hanging pendant lights.

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

Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

S$194

includes taxes & fees

24 Oct - 25 Oct

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

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

An indoor swimming pool with clear glass walls, wooden beams, and large windows.

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

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

S$146

includes taxes & fees

8 Nov - 9 Nov

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

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

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

A historic stone building with a large arched window and a small balcony.

Castello di Tornano Wine Resort

Gaiole in Chianti

S$225

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

S$164

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

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

Belvedere di San Leonino

Castellina in Chianti

S$167

includes taxes & fees

10 Oct - 11 Oct

A covered outdoor seating area with a tiled roof, surrounded by lush greenery and a view of distant hills.

An outdoor patio area with tables and chairs, a reception desk, and potted plants.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery.

A view from a covered outdoor area with a paved floor, leading to a garden with various plants and a distant landscape.

Hotel Villa San Giorgio

Poggibonsi

S$86

includes taxes & fees

8 Nov - 9 Nov

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

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

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.

Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

S$152

includes taxes & fees

21 Oct - 22 Oct

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

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

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

A stone building with a window and a light fixture.

Agriturismo San Sano

Gaiole in Chianti

S$106

includes taxes & fees

2 Nov - 3 Nov

View all properties

4-star hotels with free breakfast in Chianti Region

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

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

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.

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

S$164

includes taxes & fees

1 Nov - 2 Nov

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.

An indoor dining area with stone walls, tables set with tablecloths and chairs, and hanging pendant lights.

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

Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

S$194

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

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

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

S$108

includes taxes & fees

8 Nov - 9 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 person relaxing in a hot tub with a view of a building and trees in the background.

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

Belvedere di San Leonino

Castellina in Chianti

S$167

includes taxes & fees

10 Oct - 11 Oct

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

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

An indoor swimming pool with clear glass walls, wooden beams, and large windows.

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

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

S$146

includes taxes & fees

8 Nov - 9 Nov

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

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

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.

Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

S$152

includes taxes & fees

21 Oct - 22 Oct

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

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.

A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.

Relais Vignale & Spa

Radda in Chianti

S$287

includes taxes & fees

22 Oct - 23 Oct

A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.

A dining area with wooden tables and chairs, large windows offering a view of a forested landscape.

A breakfast buffet with various pastries, fruits, and beverages.

A swimming pool with lounge chairs and a pergola, surrounded by a garden and a building with a tiled roof.

Villa Sabolini

Colle di Val d'Elsa

S$119

includes taxes & fees

3 Nov - 4 Nov

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.

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

A pool area with lounge chairs, surrounded by well-maintained lawns and trees, with a view of rolling hills in the background.

Palazzo Squarcialupi

Castellina in Chianti

S$289

includes taxes & fees

18 Oct - 19 Oct

A clear swimming pool with a view of a lush green landscape and distant hills.

A courtyard with outdoor seating, a gravel path, and a building covered in ivy.

A bar area with a fireplace, bar stools, a table with bottles, and a shelf with glasses.

A garden with pink roses, a lawn, and a white umbrella.

Villa Le Barone

Greve in Chianti

S$361

includes taxes & fees

25 Oct - 26 Oct

View all properties

5-star hotels with free breakfast in Chianti Region

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

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.

A swimming pool with stone walls and a stone pathway leading to a building with multiple floors and a balcony.

Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

S$479

includes taxes & fees

30 Oct - 31 Oct

A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.

An indoor dining area with wooden tables and chairs, hanging baskets, and large windows offering a view of the outdoors.

A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.

A bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.

Borgo Vescine

Radda in Chianti

S$590

includes taxes & fees

6 Nov - 7 Nov

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

A large indoor swimming pool with clear water, surrounded by modern architecture and a glass railing.

An arched stone structure with a view of a landscaped garden and a building with outdoor seating.

A spacious living area with a high arched ceiling, a sofa set, and a glass coffee table.

The Club House

Castelnuovo Berardenga

S$482

includes taxes & fees

2 Nov - 3 Nov

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

A compact living space with a wooden ceiling, a white sofa, a small table, a potted plant, and a cabinet with circular designs.

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

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

Chapter Chianti, a Member of Design Hotels

Cavriglia

S$387

includes taxes & fees

12 Oct - 13 Oct

A large building with multiple rooms, surrounded by a field of lavender.

A swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.

An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.

An arched brick corridor leading to a dining area with tables set for a meal.

Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

S$533

includes taxes & fees

5 Nov - 6 Nov

A stone building with arched windows, a grassy courtyard, and outdoor seating.

A cozy living room with a sofa, a dining table with chairs, a hanging lamp, and a mirror on the wall.

An aerial view of a residential property with multiple buildings, a swimming pool, and landscaped gardens.

A person relaxing in a clear pool surrounded by natural scenery.

Pieve Aldina - Relais & Châteaux

Radda in Chianti

S$454

includes taxes & fees

22 Oct - 23 Oct

A spacious interior with high arched ceilings, stone walls, and a central round mirror reflecting the room. Tables and chairs are arranged for dining or socializing.

An outdoor dining area with tables and chairs, a chef preparing food, and a scenic view in the background.

An outdoor dining area with a long table set for a meal, surrounded by chairs, and string lights overhead.

A garden with tall cypress trees, a variety of shrubs, and a stone pathway.

COMO Castello Del Nero

Tavarnelle Val di Pesa

S$1,116

includes taxes & fees

30 Oct - 31 Oct

A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.

A table set for breakfast with various dishes, drinks, and a newspaper.

A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.

A restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.

Hotel Le Fontanelle

Castelnuovo Berardenga

S$663

includes taxes & fees

21 Oct - 22 Oct

A historic stone building with multiple windows and a courtyard.

An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.

A room with a large window overlooking a landscape with trees and hills. There are two upholstered sofas with a patterned rug in the center.

A stone building with outdoor seating and a garden with roses.

Borgo San Felice Resort

Castelnuovo Berardenga

S$1,029

includes taxes & fees

11 Oct - 12 Oct

A large building with a swimming pool, surrounded by greenery and outdoor lighting.

A courtyard with a lawn, seating area, and a weeping willow tree.

A dining area with tables and chairs, a kitchen in the background, and a patterned wall.

A large, multi-story building with a symmetrical facade, multiple windows, and a central entrance.

LHP Certaldo Resort

Certaldo

S$187

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 Chianti Region Hotel Reviews

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

8/10 Good

"Beautiful views, good location, nice restaurants nearby, friendly staff, lovely breakfast. The heated pool is a nice touch but was always busy, even now, out of season. Sadly, the place felt a little bit run down in the outdoor areas, broken / rotten outdoor furniture and a lot of rubbish dumped around the car park. Beware the huge ants if you plan to stay in the ‘treehouse’; which we felt would benefit from a little renovation, redecoration and sealing better against insects."

Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent

"Simply amazing. A nice break in a busy trip with beautiful views and lots of space. Just book a villa, they are incredible. I also loved the wine tour and diner at the castle. Only wish they would ship wine to Canada had one of the best white wines I ever tasted there."

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 Toscana Ambassador

Hotel Toscana Ambassador

8/10 Good

"Close to train station"

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."

Park Hotel Chianti

Park Hotel Chianti

10/10 Excellent

"The staff are very helpful and kind."

COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent

"The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back."

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