Hotels with Swimming Pool, Chianti Region Tuscany

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

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Check availability on Chianti Region Hotels with Swimming Pool

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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.

P20,725

P23,501 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.

P10,848

P14,093 total

includes taxes & fees

Oct 19 - Oct 20

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.

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.

P10,363

P11,821 total

includes taxes & fees

Nov 3 - Nov 4

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.

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.

4. 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.

P8,912

P10,225 total

includes taxes & fees

Nov 9 - Nov 10

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

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

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

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

5. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Float in tuscan splendor with vineyard views from two pools at this wine country hotel.

P23,946

P27,044 total

includes taxes & fees

Nov 3 - Nov 4

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

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.

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

6. Dievole Wine Resort

Castelnuovo Berardenga

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

P17,098

P19,371 total

includes taxes & fees

Nov 9 - Nov 10

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

A dining table with wine glasses, a bottle, and plates of food, set against a window with a view of a balcony and flowers.

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

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

7. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Sun-kissed pools in tuscan splendor beckon with historic charm and breathtaking views.

P6,921

P8,036 total

includes taxes & fees

Nov 1 - Nov 2

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

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

8. Castello La Leccia

Castellina in Chianti

Castello La Leccia's seasonal pool offers Tuscan countryside refreshment and vineyard views all summer long.

P12,598

P14,139 total

includes taxes & fees

Nov 2 - Nov 3

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

Castello La Leccia

Castellina in Chianti

P12,598

P14,139 total

includes taxes & fees

Nov 2 - Nov 3

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

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

Castello di Tornano Wine Resort

Gaiole in Chianti

P9,549

P11,067 total

includes taxes & fees

Oct 25 - Oct 26

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

P11,473

P12,620 total

includes taxes & fees

Oct 29 - Oct 30

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

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

Belvedere di San Leonino

Castellina in Chianti

P6,815

P7,919 total

includes taxes & fees

Oct 13 - Oct 14

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

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

A modern spa area with a wooden sauna, a glass-enclosed shower, and a marble-floored pool.

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

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

P6,784

P7,603 total

includes taxes & fees

Nov 8 - Nov 9

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 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.

Borgo di Pietrafitta Relais

Castellina in Chianti

P5,565

P6,403 total

includes taxes & fees

Oct 25 - Oct 26

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

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

P4,865

P5,773 total

includes taxes & fees

Nov 11 - Nov 12

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

A pool area with a view of a hilly landscape.

A bedroom with a large bed, a bedside table, and a chair.

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

Borgo Del Cabreo

Greve in Chianti

P14,968

P16,747 total

includes taxes & fees

Oct 13 - Oct 14

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

P8,912

P10,225 total

includes taxes & fees

Nov 9 - Nov 10

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

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

P6,921

P8,036 total

includes taxes & fees

Nov 1 - Nov 2

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4-star hotels with pools in Chianti Region

Belvedere di San Leonino

Castellina in Chianti

P6,815

P7,919 total

includes taxes & fees

Oct 13 - Oct 14

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

P6,921

P8,036 total

includes taxes & fees

Nov 1 - Nov 2

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

P6,784

P7,603 total

includes taxes & fees

Nov 8 - Nov 9

Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

P8,912

P10,225 total

includes taxes & fees

Nov 9 - Nov 10

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

Hotel Villa Campomaggio

Radda in Chianti

P10,363

P11,821 total

includes taxes & fees

Nov 3 - Nov 4

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

P4,865

P5,773 total

includes taxes & fees

Nov 11 - Nov 12

Relais Vignale & Spa

Radda in Chianti

P10,848

P14,093 total

includes taxes & fees

Oct 19 - Oct 20

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

P15,656

P17,644 total

includes taxes & fees

Oct 25 - Oct 26

A spa area with a stone ceiling, a pool, and two sun loungers.

A courtyard with outdoor seating, stone walls, and a staircase.

A spa area with multiple white massage chairs arranged in a row, a brick ceiling, and a staircase in the background.

A buffet area with various fruits and a bar with bottles.

Hotel Palazzo San niccolò & Spa

Radda in Chianti

P6,104

P7,137 total

includes taxes & fees

Nov 11 - Nov 12

A spa area with a stone ceiling, a large bathtub, and a seating area.

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

A rectangular pool with clear water, surrounded by white lounge chairs and a grassy area.

A bedroom with a bed, bedside tables, a sofa, a window with curtains, and a wall with a painting.

Palazzo Squarcialupi

Castellina in Chianti

P12,183

P13,823 total

includes taxes & fees

Oct 18 - Oct 19

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5-star hotels with pools in Chianti Region

A bedroom with a bed, two bedside tables, a mirror, and a window with curtains.

An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.

Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

P20,725

P23,501 total

includes taxes & fees

Oct 30 - Oct 31

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

Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

P23,946

P27,044 total

includes taxes & fees

Nov 3 - Nov 4

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 aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.

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

Borgo Vescine

Radda in Chianti

P29,361

P32,860 total

includes taxes & fees

Nov 4 - Nov 5

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

Chapter Chianti, a Member of Design Hotels

Cavriglia

P16,887

P18,998 total

includes taxes & fees

Oct 13 - Oct 14

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

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

A bedroom with a wooden ceiling, a stone wall, a bed, a desk, a chair, a sofa, and a window with curtains.

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

Pieve Aldina - Relais & Châteaux

Radda in Chianti

P21,832

P24,578 total

includes taxes & fees

Oct 22 - Oct 23

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

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

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

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

The Club House

Castelnuovo Berardenga

P22,429

P25,375 total

includes taxes & fees

Nov 11 - Nov 12

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.

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

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

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

COMO Castello Del Nero

Tavarnelle Val di Pesa

P46,056

P51,225 total

includes taxes & fees

Nov 11 - Nov 12

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

P34,450

P38,599 total

includes taxes & fees

Oct 21 - Oct 22

A historic stone building with multiple windows and a courtyard.

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.

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

Borgo San Felice Resort

Castelnuovo Berardenga

P47,464

P52,914 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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

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

LHP Certaldo Resort

Certaldo

P6,982

P8,102 total

includes taxes & fees

Oct 19 - Oct 20

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.

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Top Chianti Region Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."

Villa I Barronci Resort & Spa

10/10 Excellent

"Great spot and friendly staff."

Castello Vicchiomaggio

10/10 Excellent

"A unique stay with a picturesque view. Breakfast, lunch, and dinner were fantastic. The property was great for relaxing at but also a good launching spot for exploring some of the nearby towns and sites."

Borgo Vescine

10/10 Excellent

"The staff was amazing and incredibly kind."

Relais Vignale & Spa

10/10 Excellent

"In a convenient location."

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."

Hu Norcenni Girasole Village

10/10 Excellent

"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."

Villa Casagrande Resort & SPA

8/10 Good

"Restaurant was great. Towels have too much use"

Park Hotel Chianti

10/10 Excellent

"The staff are very helpful and kind."

Hotels with Swimming Pool in Chianti Region, Tuscany

Change your mind

Treat yourself

Be picky

Check availability on Chianti Region Hotels with Swimming Pool

Our top choices for Chianti Region hotels with a pool

1. Castello di Spaltenna- Small Luxury Hotels of the World

2. Relais Vignale & Spa

3. Hotel Villa Campomaggio

4. Hotel Borgo di Cortefreda Relais - Place of Charme

5. Borgo Scopeto Wine & Country Relais

6. Dievole Wine Resort

7. Palazzo Leopoldo Dimora Storica & Spa

8. Castello La Leccia

9. Chapter Chianti, a Member of Design Hotels

10. COMO Castello Del Nero

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

Hotels with pools and free breakfast in Chianti Region

Castello La Leccia

Castello di Tornano Wine Resort

Castello Vicchiomaggio

Belvedere di San Leonino

Villa Casagrande Resort & SPA

Borgo di Pietrafitta Relais

Villa I Barronci Resort & Spa

Borgo Del Cabreo

Hotel Borgo di Cortefreda Relais - Place of Charme

Palazzo Leopoldo Dimora Storica & Spa

4-star hotels with pools in Chianti Region

Belvedere di San Leonino

Palazzo Leopoldo Dimora Storica & Spa

Villa Casagrande Resort & SPA

Hotel Borgo di Cortefreda Relais - Place of Charme

Hotel Villa Campomaggio

Villa I Barronci Resort & Spa

Relais Vignale & Spa

Villa Le Barone

Hotel Palazzo San niccolò & Spa

Palazzo Squarcialupi

5-star hotels with pools in Chianti Region

Castello di Spaltenna- Small Luxury Hotels of the World

Borgo Scopeto Wine & Country Relais

Borgo Vescine

Chapter Chianti, a Member of Design Hotels

Pieve Aldina - Relais & Châteaux

The Club House

COMO Castello Del Nero

Hotel Le Fontanelle

Borgo San Felice Resort

LHP Certaldo Resort

Top Chianti Region Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

Villa I Barronci Resort & Spa

Castello Vicchiomaggio

Borgo Vescine

Relais Vignale & Spa

Villa Le Barone

Hu Norcenni Girasole Village

Villa Casagrande Resort & SPA

Park Hotel Chianti

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