Book the Best Hotels with POOL in Chianti Region in 2026

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Check availability on Chianti Region Hotels with a Pool

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

1. Borgo di Pietrafitta Relais

Castellina in Chianti

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

CA $126

CA $145 total

includes taxes & fees

Oct 14 - Oct 15

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

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

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.

CA $190

CA $213 total

includes taxes & fees

Sep 30 - Oct 1

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

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

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

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

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.

CA $283

CA $321 total

includes taxes & fees

Oct 12 - Oct 13

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

A rustic stone building with a garden in front.

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

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.

CA $177

CA $204 total

includes taxes & fees

Sep 23 - Sep 24

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

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

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.

5. Chapter Chianti, a Member of Design Hotels

Cavriglia

CA $386

CA $434 total

includes taxes & fees

Oct 6 - Oct 7

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

A view through an arched window of a lush landscape with trees and hills.

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.

CA $297

CA $326 total

includes taxes & fees

Oct 14 - Oct 15

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

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

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.

7. Castello Vicchiomaggio

Greve in Chianti

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

CA $337

CA $371 total

includes taxes & fees

Sep 29 - Sep 30

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

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

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

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.

CA $248

CA $322 total

includes taxes & fees

Oct 8 - Oct 9

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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

CA $337

CA $377 total

includes taxes & fees

Oct 7 - Oct 8

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

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.

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

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

CA $151

CA $176 total

includes taxes & fees

Oct 15 - Oct 16

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 restaurant with multiple tables set for dining, featuring wooden beams and a chandelier.

Villa Le Barone

Greve in Chianti

CA $327

CA $369 total

includes taxes & fees

Oct 11 - Oct 12

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

A room with a fireplace, two armchairs, a sofa, a chandelier, and a large mirror on the wall.

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

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

Villa San Lucchese

Poggibonsi

CA $176

CA $203 total

includes taxes & fees

Sep 16 - Sep 17

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.

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

CA $190

CA $213 total

includes taxes & fees

Sep 30 - Oct 1

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

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.

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

Palagina la Dimora

Figline e Incisa Valdarno

CA $174

CA $194 total

includes taxes & fees

Sep 29 - Sep 30

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

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.

A hotel reception area with a reception desk, a hallway leading to the rooms, and a staircase.

B&B Poggiobonizio

Poggibonsi

CA $99

CA $115 total

includes taxes & fees

Sep 18 - Sep 19

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

CA $177

CA $204 total

includes taxes & fees

Sep 23 - Sep 24

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

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

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.

Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa

CA $195

CA $225 total

includes taxes & fees

Oct 7 - Oct 8

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

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

A modern interior with a bar area, seating, and a staircase.

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

Locanda le Piazze

Castellina in Chianti

CA $527

CA $589 total

includes taxes & fees

Sep 24 - Sep 25

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