Top Hotels with Swimming Pools in Chianti Region | Expedia.com.sg

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Check availability on Chianti Region Hotels with Swimming Pools

Tonight

14 Sept - 15 Sept

Tomorrow

15 Sept - 16 Sept

This weekend

18 Sept - 20 Sept

Next weekend

25 Sept - 27 Sept

Our top choices for Chianti Region hotels with a pool

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 striped sofa.

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.

1. Borgo di Pietrafitta Relais

Castellina in Chianti

Countryside farm stay's outdoor pool beckons with scenic vineyard views.

S$199

includes taxes & fees

4 Oct - 5 Oct

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

A stone-walled room with a brick ceiling, featuring a row of white sofas and a small table with a candle.

A courtyard with stone flooring, arched walkways, and a central fountain.

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

2. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Swim through captivating seasons at this hotel with both indoor and outdoor pools, spa treatments, and an attached winery.

S$194

includes taxes & fees

30 Sept - 1 Oct

A landscaped garden with a swimming pool, a vineyard in the background, and a stone pathway.

A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

A spa area with stone flooring, wooden chairs, a table with amenities, and a view of a garden through a glass door.

An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.

3. Hotel Villa Campomaggio

Radda in Chianti

Soak in mountain views from the sun-drenched outdoor pool at this Tuscan retreat where spa treatments and regional cuisine await.

S$293

includes taxes & fees

12 Oct - 13 Oct

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

A rustic stone building with a garden in front.

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

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.

4. Belvedere di San Leonino

Castellina in Chianti

Scenic Tuscan escape with a poolside paradise and winery at your doorstep.

S$186

includes taxes & fees

15 Oct - 16 Oct

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.

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.

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

5. Chapter Chianti, a Member of Design Hotels

Cavriglia

S$397

includes taxes & fees

6 Oct - 7 Oct

A pool with a pink flamingo float, surrounded by lounge chairs and a stone deck.

A bedroom with a bed, a chair, a red table, and a wardrobe.

A terrace with two chairs and a table, overlooking a scenic landscape with hills and a sunset.

A multi-story building with a tiled roof, surrounded by greenery and trees.

6. La Pensione di Vignamaggio

Panzano in Chianti

Dive into poolside tranquility with a seasonal outdoor pool nestled among gardens and a charming terrace at this Italian retreat.

S$302

includes taxes & fees

12 Oct - 13 Oct

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

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

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

A bedroom with a large arched window, a bed, a hanging light fixture, and a view of a green landscape.

7. Castello Vicchiomaggio

Greve in Chianti

Refreshing infinity pool with breathtaking views awaits at this charming Tuscan farm stay with winery.

S$339

includes taxes & fees

29 Sept - 30 Sept

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

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

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

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

8. Relais Vignale & Spa

Radda in Chianti

Discover a seasonal rooftop sanctuary with dual pools, poolside bar service, and stunning vineyard views in historic wine country.

S$294

includes taxes & fees

8 Oct - 9 Oct

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Choose what matters most at hotels with a pool in Chianti Region

Breakfast included

4 stars

5 stars

Hot tub

Spa

Hotels with pools and free breakfast in Chianti Region

A rustic stone interior with a dining area, two armchairs, a table with a lamp, and a view through an arched doorway.

A stone building with a courtyard, a tall tree, and a view of the countryside.

A narrow street with stone buildings, a wrought iron gate, and a street lamp.

A swimming pool with lounge chairs and a pergola, surrounded by a landscaped garden and a view of a forested hillside.

Castello di Volpaia

Radda in Chianti

S$343

includes taxes & fees

14 Oct - 15 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 pathway lined with wooden fences and benches, leading to a covered seating area with tables and chairs.

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

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

S$161

includes taxes & fees

15 Oct - 16 Oct

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

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.

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

Villa Le Barone

Greve in Chianti

S$337

includes taxes & fees

11 Oct - 12 Oct

An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.

A clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.

A room with a sofa, a desk, a bunk bed, and a patterned floor.

A yellow building with stone pillars, multiple windows, and a statue in the garden.

Villa San Lucchese

Poggibonsi

S$182

includes taxes & fees

14 Oct - 15 Oct

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

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

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

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

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

S$194

includes taxes & fees

30 Sept - 1 Oct

A well-maintained garden with geometric hedges and a pathway leading to a building with multiple windows and outdoor seating.

A restaurant with tables set for dining, large umbrellas, and a view of the landscape.

A stone building with a large wooden door and arched entrance, flanked by potted plants.

A room with a large window offering a view of a vineyard and distant hills.

Palagina la Dimora

Figline e Incisa Valdarno

S$179

includes taxes & fees

28 Sept - 29 Sept

A wooden chair and table with a bottle and wine glass.

A circular pond with a wooden fence, surrounded by well-maintained bushes and trees.

A historic building with a clock tower, surrounded by trees and a stone wall.

A hotel room with a wooden desk, a television, two beds, and a large window with curtains.

B&B Poggiobonizio

Poggibonsi

S$105

includes taxes & fees

21 Sept - 22 Sept

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

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.

Belvedere di San Leonino

Castellina in Chianti

S$186

includes taxes & fees

15 Oct - 16 Oct

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

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

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.

Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa

S$198

includes taxes & fees

15 Oct - 16 Oct

A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.

A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.

A vineyard landscape with rows of grapevines and a person holding a glass.

A spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.

Locanda le Piazze

Castellina in Chianti

S$538

includes taxes & fees

24 Sept - 25 Sept

View all properties

4-star hotels with pools in Chianti Region

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

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

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

S$161

includes taxes & fees

15 Oct - 16 Oct

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

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.

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

Villa Le Barone

Greve in Chianti

S$337

includes taxes & fees

11 Oct - 12 Oct

A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

A spa area with stone flooring, wooden chairs, a table with amenities, and a view of a garden through a glass door.

An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.

A courtyard with a stone building, wooden pergola, and raised garden beds with various plants.

Hotel Villa Campomaggio

Radda in Chianti

S$293

includes taxes & fees

12 Oct - 13 Oct

An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.

A clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.

A room with a sofa, a desk, a bunk bed, and a patterned floor.

A yellow building with stone pillars, multiple windows, and a statue in the garden.

Villa San Lucchese

Poggibonsi

S$182

includes taxes & fees

14 Oct - 15 Oct

A well-maintained garden with geometric hedges and a pathway leading to a building with multiple windows and outdoor seating.

A restaurant with tables set for dining, large umbrellas, and a view of the landscape.

A stone building with a large wooden door and arched entrance, flanked by potted plants.

A room with a large window offering a view of a vineyard and distant hills.

Palagina la Dimora

Figline e Incisa Valdarno

S$179

includes taxes & fees

28 Sept - 29 Sept

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

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

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

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

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

S$194

includes taxes & fees

30 Sept - 1 Oct

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

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

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.

Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa

S$198

includes taxes & fees

15 Oct - 16 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 poolside area with lounge chairs and a view of the night sky.

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.

Belvedere di San Leonino

Castellina in Chianti

S$186

includes taxes & fees

15 Oct - 16 Oct

A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.

A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.

A vineyard landscape with rows of grapevines and a person holding a glass.

A spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.

Locanda le Piazze

Castellina in Chianti

S$538

includes taxes & fees

24 Sept - 25 Sept

A person sitting in a corner of a room with tiled walls and a bench.

A poolside area with lounge chairs, umbrellas, and a swimming pool.

A fountain in a park with tall trees and a clear sky.

A covered outdoor dining area with tables and chairs, a pool, and a garden in the background.

Hotel Il Piccolo Castello

Monteriggioni

S$214

includes taxes & fees

20 Sept - 21 Sept

View all properties

5-star hotels with pools in Chianti Region

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

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

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

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

Borgo Vescine

Radda in Chianti

S$1,180

includes taxes & fees

25 Sept - 26 Sept

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

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

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 pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.

Hotel Le Fontanelle

Castelnuovo Berardenga

S$719

includes taxes & fees

6 Oct - 7 Oct

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

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

A historic estate with a central courtyard, surrounded by lush gardens and vineyards.

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

Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

S$818

includes taxes & fees

8 Oct - 9 Oct

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 room with a large window offering a view of a hilly landscape. There is a sofa with patterned upholstery and a lamp on a side table.

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

Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

S$597

includes taxes & fees

5 Oct - 6 Oct

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

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

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

A bar area with a high ceiling, wooden beams, and a bar counter with stools.

Chapter Chianti, a Member of Design Hotels

Cavriglia

S$397

includes taxes & fees

6 Oct - 7 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 large, multi-story building with a symmetrical facade, multiple windows, and a central entrance.

A courtyard with a stone bridge over a small water feature, surrounded by greenery and a building with arched windows.

LHP Certaldo Resort

Certaldo

S$205

includes taxes & fees

13 Oct - 14 Oct

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

An indoor dining area with brick arches, tables set for dining, and a view of the outdoors.

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

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

The Club House

Castelnuovo Berardenga

S$1,203

includes taxes & fees

27 Sept - 28 Sept

An outdoor dining area with wicker chairs and tables, white tablecloths, and umbrellas, overlooking a scenic landscape.

A dining area with stone walls, wooden beams, and round tables set for a meal.

A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.

A bar area with a dark bar counter, red chairs, and a fireplace.

Villa Le Calvane

Montespertoli

S$861

includes taxes & fees

3 Oct - 4 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 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.

A resort with a swimming pool, terraced gardens, and a view of rolling hills.

COMO Castello Del Nero

Tavarnelle Val di Pesa

S$1,431

includes taxes & fees

1 Oct - 2 Oct

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

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

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

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

Pieve Aldina - Relais & Châteaux

Radda in Chianti

S$530

includes taxes & fees

30 Sept - 1 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

Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent

"Clean, comfortable, upgraded, true a/c, and beautiful"

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."

Villa Le Barone

Villa Le Barone

10/10 Excellent

"Excellent stay with wonderful , friendly staff!"

Palagina la Dimora

Palagina la Dimora

10/10 Excellent

"Wonderful Tuscany escape. Charming villa with spectacular views and amazing restaurant overlooking vineyards. Tecla at reception and the rest of the staff made the stay so special. Can’t wait to return!"

Hotel Villa Campomaggio

Hotel Villa Campomaggio

10/10 Excellent

"This resort is one of the most beautiful properties I have ever stayed in. Free use of the spa just was icing on the cake! Great breakfast spread and our dinner in the restaurant was delicious! We will be back!!"

Villa Il Palagio

Villa Il Palagio

10/10 Excellent

"Great loved everything thank you!"

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village

10/10 Excellent

"Amazing venue , lots of kids entertainment. Lots of facilities- shops restaurants. Splash parks were brilliant. Highly recommended."

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

10/10 Excellent

"Incredible property, steeped in history. The rooms are beautifully traditional and the staff incredibly friendly. A beautiful place to unwind for a few days in Tuscany! We would re-book in a heartbeat."

Park Hotel Chianti

Park Hotel Chianti

10/10 Excellent

"A clean hotel, we got upgraded so no issues on room was updated and pleasant, AC could have been stronger but was ok, nice buffet breakfast with good assortment of food:) Front desk ladies were helpful in giving restaurant suggestions in the surrounding area 👌"

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