The Best Hotels with a Pool in Chianti Region from ￥13,724 in 2026

A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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Our top choices for Chianti Region hotels with a pool

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.

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.

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

Serene pools with vineyard views offer both indoor and outdoor aquatic escapes.

￥52,537

￥59,574 total

includes taxes & fees

Oct 30 - Oct 31

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

2. 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.

￥25,560

￥33,591 total

includes taxes & fees

Oct 26 - Oct 27

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

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

3. Dievole Wine Resort

Castelnuovo Berardenga

Splash into luxury at a Tuscan wine resort with two outdoor pools and vineyard views.

￥42,365

￥48,028 total

includes taxes & fees

Oct 28 - Oct 29

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

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.

4. COMO Castello Del Nero

Tavarnelle Val di Pesa

Seasonal outdoor pool oasis in Tuscan wine country offers private poolside dining and luxury spa treatments.

￥124,991

￥138,917 total

includes taxes & fees

Oct 30 - Oct 31

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

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

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

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

5. 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.

￥26,824

￥30,572 total

includes taxes & fees

Nov 2 - Nov 3

A poolside area with lounge chairs and umbrellas.

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

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

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

6. Chapter Chianti, a Member of Design Hotels

Cavriglia

￥42,648

￥47,979 total

includes taxes & fees

Oct 14 - Oct 15

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

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

7. Hotel Le Fontanelle

Castelnuovo Berardenga

Dive into tranquil luxury at this hotel's indoor and seasonal outdoor pools, complemented by a poolside bar and loungers.

￥76,850

￥86,319 total

includes taxes & fees

Oct 21 - Oct 22

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

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

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

A bartender at a bar with a variety of liquor bottles in the background.

8. Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa

Discover a Tuscan oasis with a seasonal pool sanctuary, loungers for sunbathing, and poolside drinks service in wine country.

￥20,884

￥24,042 total

includes taxes & fees

Oct 24 - Oct 25

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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

Relais Vignale & Spa

Radda in Chianti

￥25,560

￥33,591 total

includes taxes & fees

Oct 26 - Oct 27

Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

￥52,537

￥59,574 total

includes taxes & fees

Oct 30 - Oct 31

A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

Dievole Wine Resort

Castelnuovo Berardenga

￥42,365

￥48,028 total

includes taxes & fees

Oct 28 - Oct 29

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

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

A room with a view of a valley, a stone shelf with flowers, a wooden bench, and a fireplace.

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

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

￥18,468

￥21,380 total

includes taxes & fees

Nov 2 - Nov 3

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

A reception area with a wooden ceiling, a reception desk, and seating.

Chapter Chianti, a Member of Design Hotels

Cavriglia

￥42,648

￥47,979 total

includes taxes & fees

Oct 14 - Oct 15

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

Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa

￥20,884

￥24,042 total

includes taxes & fees

Oct 24 - Oct 25

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.

Castello Vicchiomaggio

Greve in Chianti

￥26,914

￥29,606 total

includes taxes & fees

Oct 29 - Oct 30

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

￥45,021

￥50,236 total

includes taxes & fees

Oct 28 - Oct 29

COMO Castello Del Nero

Tavarnelle Val di Pesa

￥124,991

￥138,917 total

includes taxes & fees

Oct 30 - Oct 31

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

Villa Le Barone

Greve in Chianti

￥39,688

￥44,726 total

includes taxes & fees

Oct 25 - Oct 26

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