🏊 Top 10 Chianti Region Hotels with Swimming Pool

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 sunlit patio with a glass roof, stone walls, and outdoor seating.

A stone building with a garden, tall trees, and a clear blue sky.

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

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.

RM1,342

RM1,522 total

includes taxes & fees

30 Oct - 31 Oct

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

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.

RM660

RM866 total

includes taxes & fees

16 Oct - 17 Oct

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

A room with a view of a forest through a window, a table with a lamp, and a chair.

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

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

3. Dievole Wine Resort

Castelnuovo Berardenga

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

RM1,107

RM1,254 total

includes taxes & fees

9 Nov - 10 Nov

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.

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.

4. 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.

RM671

RM766 total

includes taxes & fees

3 Nov - 4 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.

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

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

5. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

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

RM569

RM654 total

includes taxes & fees

14 Nov - 15 Nov

A swimming pool with a view of a forest through large windows.

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.

6. Chapter Chianti, a Member of Design Hotels

Cavriglia

RM1,094

RM1,230 total

includes taxes & fees

15 Oct - 16 Oct

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

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

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.

7. Castello Vicchiomaggio

Greve in Chianti

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

RM899

RM988 total

includes taxes & fees

29 Oct - 30 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 room with a wooden ceiling, a sofa, a coffee table, a lamp, and a TV.

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

8. Villa Le Barone

Greve in Chianti

Dive into luxury at this Tuscan retreat with 2 outdoor pools, mountain views, and a poolside bar for ultimate relaxation.

RM1,010

RM1,138 total

includes taxes & fees

31 Oct - 1 Nov

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

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

A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a tray of items, and a window with curtains.

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

Castello La Leccia

Castellina in Chianti

RM816

RM916 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

Castello di Tornano Wine Resort

Gaiole in Chianti

RM618

RM717 total

includes taxes & fees

25 Oct - 26 Oct

Castello Vicchiomaggio

Greve in Chianti

RM899

RM988 total

includes taxes & fees

29 Oct - 30 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.

Belvedere di San Leonino

Castellina in Chianti

RM437

RM508 total

includes taxes & fees

16 Oct - 17 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.

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

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

RM441

RM494 total

includes taxes & fees

8 Nov - 9 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 cozy living room with a stone fireplace, striped sofas, and a coffee table.

A dining area with a stone wall, wooden beams, and a table set for four with wine glasses and plates.

A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and lush greenery, overlooking a valley.

Borgo di Pietrafitta Relais

Castellina in Chianti

RM360

RM414 total

includes taxes & fees

27 Oct - 28 Oct

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

RM323

RM383 total

includes taxes & fees

13 Nov - 14 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 pool area with a view of a hilly landscape.

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.

Borgo Del Cabreo

Greve in Chianti

RM969

RM1,085 total

includes taxes & fees

16 Oct - 17 Oct

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

Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

RM569

RM654 total

includes taxes & fees

14 Nov - 15 Nov

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

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

RM448

RM520 total

includes taxes & fees

1 Nov - 2 Nov

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