TOP Hotels with Swimming Pool in Chianti Region for 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.

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

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.

₹31,913

₹36,188 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 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.

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.

₹16,704

₹21,701 total

includes taxes & fees

19 Oct - 20 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.

₹15,957

₹18,203 total

includes taxes & fees

3 Nov - 4 Nov

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.

4. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

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

₹37,325

₹42,141 total

includes taxes & fees

6 Nov - 7 Nov

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

A bartender at a bar with a variety of liquor bottles 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 stone building with a wooden door and an arched window.

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.

₹12,568

₹14,475 total

includes taxes & fees

12 Nov - 13 Nov

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

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.

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

6. Dievole Wine Resort

Castelnuovo Berardenga

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

₹23,170

₹26,353 total

includes taxes & fees

9 Nov - 10 Nov

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 splendour beckon with historic charm and breathtaking views.

₹10,658

₹12,374 total

includes taxes & fees

1 Nov - 2 Nov

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

8. Chapter Chianti, a Member of Design Hotels

Cavriglia

₹26,004

₹29,255 total

includes taxes & fees

13 Oct - 14 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 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 dining area with a table set for two, featuring wine bottles and bread.

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

₹19,399

₹21,772 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 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.

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

Castello di Tornano Wine Resort

Gaiole in Chianti

₹14,704

₹17,042 total

includes taxes & fees

25 Oct - 26 Oct

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

Castello Vicchiomaggio

Greve in Chianti

₹17,667

₹19,434 total

includes taxes & fees

29 Oct - 30 Oct

A small, square, concrete structure with a rough texture, possibly a niche or recess in a wall.

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

A rustic stone building with a garden in front.

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.

Belvedere di San Leonino

Castellina in Chianti

₹10,381

₹12,069 total

includes taxes & fees

13 Oct - 14 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.

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

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

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

₹10,446

₹11,707 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 stone building with a courtyard, a covered seating area, and a small bell tower.

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

₹8,570

₹9,860 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

₹7,191

₹8,561 total

includes taxes & fees

11 Nov - 12 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 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.

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

Borgo Del Cabreo

Greve in Chianti

₹20,053

₹22,491 total

includes taxes & fees

13 Oct - 14 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

₹12,568

₹14,475 total

includes taxes & fees

12 Nov - 13 Nov

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

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

₹10,658

₹12,374 total

includes taxes & fees

1 Nov - 2 Nov

View all properties

4-star hotels with pools in Chianti Region

Belvedere di San Leonino

Castellina in Chianti

₹10,381

₹12,069 total

includes taxes & fees

13 Oct - 14 Oct

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

₹10,658

₹12,374 total

includes taxes & fees

1 Nov - 2 Nov

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

₹10,446

₹11,707 total

includes taxes & fees

8 Nov - 9 Nov

Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

₹12,568

₹14,475 total

includes taxes & fees

12 Nov - 13 Nov

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

Hotel Villa Campomaggio

Radda in Chianti

₹15,957

₹18,203 total

includes taxes & fees

3 Nov - 4 Nov

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

₹7,191

₹8,561 total

includes taxes & fees

11 Nov - 12 Nov

Relais Vignale & Spa

Radda in Chianti

₹16,704

₹21,701 total

includes taxes & fees

19 Oct - 20 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 restaurant with multiple tables set for dining, featuring wooden beams and a chandelier.

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

Villa Le Barone

Greve in Chianti

₹24,108

₹27,169 total

includes taxes & fees

25 Oct - 26 Oct

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

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

A luxurious room with ornate ceiling artwork, plush seating, and elegant lighting fixtures.

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

Hotel Palazzo San niccolò & Spa

Radda in Chianti

₹9,399

₹10,989 total

includes taxes & fees

11 Nov - 12 Nov

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

A historic building with a courtyard, stone arches, and a tiled roof.

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

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

Palazzo Squarcialupi

Castellina in Chianti

₹18,760

₹21,286 total

includes taxes & fees

18 Oct - 19 Oct

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5-star hotels with pools in Chianti Region

Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

₹31,913

₹36,188 total

includes taxes & fees

30 Oct - 31 Oct

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

₹37,325

₹42,141 total

includes taxes & fees

6 Nov - 7 Nov

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

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.

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

Borgo Vescine

Radda in Chianti

₹41,595

₹46,621 total

includes taxes & fees

4 Nov - 5 Nov

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

A compact living space with a wooden ceiling, a white sofa, a small table, a potted plant, and a cabinet with circular designs.

Chapter Chianti, a Member of Design Hotels

Cavriglia

₹26,004

₹29,255 total

includes taxes & fees

13 Oct - 14 Oct

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

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.

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

Pieve Aldina - Relais & Châteaux

Radda in Chianti

₹33,618

₹37,847 total

includes taxes & fees

22 Oct - 23 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.

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

The Club House

Castelnuovo Berardenga

₹32,465

₹36,795 total

includes taxes & fees

2 Nov - 3 Nov

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

₹70,920

₹78,879 total

includes taxes & fees

11 Nov - 12 Nov

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

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.

A table set for breakfast with various dishes, drinks, and a newspaper.

Hotel Le Fontanelle

Castelnuovo Berardenga

₹45,091

₹50,684 total

includes taxes & fees

21 Oct - 22 Oct

A historic stone building with multiple windows and a courtyard.

A pool area with lounge chairs and a service person attending to a guest.

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.

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

₹65,048

₹72,636 total

includes taxes & fees

8 Nov - 9 Nov

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 dining area with tables and chairs, a kitchen in the background, and a patterned wall.

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

LHP Certaldo Resort

Certaldo

₹10,751

₹12,477 total

includes taxes & fees

19 Oct - 20 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.

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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."

Hotel Villa Campomaggio

10/10 Excellent

"Great hotel"

Villa Casagrande Resort & SPA

8/10 Good

"Restaurant was great. Towels have too much use"

Explore a world of travel with Expedia

Book Hotels with Swimming Pool in Chianti Region on Expedia.it

Search Hotels with Swimming Pool in Chianti Region

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. Borgo Scopeto Wine & Country Relais

5. Hotel Borgo di Cortefreda Relais - Place of Charme

6. Dievole Wine Resort

7. Palazzo Leopoldo Dimora Storica & Spa

8. Chapter Chianti, a Member of Design Hotels

9. COMO Castello Del Nero

10. Castello La Leccia

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

Hotel Villa Campomaggio

Villa Casagrande Resort & SPA

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