Top 10 Hotels with Pool & Accommodation in Chianti Region from NZ$158 | Expedia

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Check availability on Chianti Region Hotels with Pool

Tonight

22 Sept - 23 Sept

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23 Sept - 24 Sept

This weekend

25 Sept - 27 Sept

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Our top choices for Chianti Region hotels with a pool

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

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

A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.

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

1. 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.

NZ$378

includes taxes & fees

8 Oct - 9 Oct

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

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

2. 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.

NZ$364

includes taxes & fees

20 Oct - 21 Oct

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

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

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.

3. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

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

NZ$340

includes taxes & fees

21 Oct - 22 Oct

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 bedroom with a bed, a chair, a red table, and a wardrobe.

A multi-story building with a tiled roof, surrounded by greenery and trees.

4. 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.

NZ$456

includes taxes & fees

22 Oct - 23 Oct

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

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.

5. Chapter Chianti, a Member of Design Hotels

Cavriglia

NZ$542

includes taxes & fees

6 Oct - 7 Oct

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

A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.

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

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

6. Borgo di Pietrafitta Relais

Castellina in Chianti

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

NZ$158

includes taxes & fees

19 Oct - 20 Oct

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

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

A woman sitting on a chair in a room with a staircase, a wall-mounted light, and a tiled floor.

A bathroom with a bathtub, a stone wall, and a wooden door.

7. Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

Sip poolside bliss at this luxury Tuscan retreat where serene mountain views frame your aquatic sanctuary.

NZ$233

includes taxes & fees

22 Oct - 23 Oct

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

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

8. 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.

NZ$257

includes taxes & fees

30 Sept - 1 Oct

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

Breakfast included

4 stars

5 stars

Spa pool

Spa

Hotels with pools and free breakfast in Chianti Region

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

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

Borgo di Pietrafitta Relais

Castellina in Chianti

NZ$158

includes taxes & fees

19 Oct - 20 Oct

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

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

A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.

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

Relais Vignale & Spa

Radda in Chianti

NZ$378

includes taxes & fees

8 Oct - 9 Oct

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

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.

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

Castello Vicchiomaggio

Greve in Chianti

NZ$311

includes taxes & fees

27 Sept - 28 Sept

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

NZ$310

includes taxes & fees

19 Oct - 20 Oct

A pool with a stone wall and a tree, surrounded by a clear sky and distant mountains.

A bedroom with a large bed, bedside lamps, a chair, and a chandelier.

A stone wall, a pink building, and a pool with a garden.

A minimalist room with a wooden desk, two chairs, a mirror, and a vase with flowers.

Villa Barberino

Meleto

NZ$303

includes taxes & fees

23 Oct - 24 Oct

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 bedroom with a bed, a chair, a red table, and a wardrobe.

A multi-story building with a tiled roof, surrounded by greenery and trees.

La Pensione di Vignamaggio

Panzano in Chianti

NZ$456

includes taxes & fees

22 Oct - 23 Oct

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

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

A woman sitting on a chair in a room with a staircase, a wall-mounted light, and a tiled floor.

A pathway lined with wooden fences and benches, leading to a covered seating area with tables and chairs.

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

NZ$233

includes taxes & fees

22 Oct - 23 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 rustic stone building with a garden in front.

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

Belvedere di San Leonino

Castellina in Chianti

NZ$252

includes taxes & fees

23 Sept - 24 Sept

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.

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.

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

NZ$257

includes taxes & fees

30 Sept - 1 Oct

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.

A bar area with a high ceiling, wooden beams, and a bar counter with stools.

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

Chapter Chianti, a Member of Design Hotels

Cavriglia

NZ$542

includes taxes & fees

6 Oct - 7 Oct

View all properties

4-star hotels with pools in Chianti Region

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

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

A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.

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

Relais Vignale & Spa

Radda in Chianti

NZ$378

includes taxes & fees

8 Oct - 9 Oct

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

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.

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

Hotel Villa Campomaggio

Radda in Chianti

NZ$364

includes taxes & fees

20 Oct - 21 Oct

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

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

A woman sitting on a chair in a room with a staircase, a wall-mounted light, and a tiled floor.

A pathway lined with wooden fences and benches, leading to a covered seating area with tables and chairs.

Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

NZ$233

includes taxes & fees

22 Oct - 23 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 rustic stone building with a garden in front.

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

Belvedere di San Leonino

Castellina in Chianti

NZ$252

includes taxes & fees

23 Sept - 24 Sept

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.

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.

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

NZ$257

includes taxes & fees

30 Sept - 1 Oct

A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.

An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.

A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

NZ$200

includes taxes & fees

22 Oct - 23 Oct

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

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

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

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

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

NZ$340

includes taxes & fees

21 Oct - 22 Oct

A pool with clear water and a row of white lounge chairs facing a scenic hillside view.

A spa room with a stone ceiling, a circular hot tub, a window, and a bench.

A spa room with a stone ceiling, a window with frosted glass, a bed with pillows, and a wall-mounted artwork.

A stone-walled hallway with a staircase, a glass table with a red cushion, and a wooden cabinet.

Palazzo Squarcialupi

Castellina in Chianti

NZ$398

includes taxes & fees

21 Oct - 22 Oct

A clear swimming pool with a view of a lush green landscape and distant hills.

A garden with pink roses, a lawn, and a white umbrella.

A bar area with a fireplace, bar stools, a table with bottles, and a shelf with glasses.

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

Villa Le Barone

Greve in Chianti

NZ$489

includes taxes & fees

23 Oct - 24 Oct

A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.

A swimming pool with lounge chairs and a pergola, surrounded by a garden and a building with a tiled roof.

A well-lit outdoor bar area with a wooden structure, surrounded by lush greenery and stone pathways.

A breakfast buffet with various pastries, fruits, and beverages.

Villa Sabolini

Colle di Val d'Elsa

NZ$257

includes taxes & fees

19 Oct - 20 Oct

View all properties

5-star hotels with pools in Chianti Region

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.

A bar area with a high ceiling, wooden beams, and a bar counter with stools.

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

Chapter Chianti, a Member of Design Hotels

Cavriglia

NZ$542

includes taxes & fees

6 Oct - 7 Oct

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

NZ$963

includes taxes & fees

21 Oct - 22 Oct

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

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

NZ$778

includes taxes & fees

21 Oct - 22 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

NZ$1,119

includes taxes & fees

22 Oct - 23 Oct

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

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.

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

NZ$1,117

includes taxes & fees

7 Oct - 8 Oct

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

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.

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

LHP Certaldo Resort

Certaldo

NZ$264

includes taxes & fees

22 Oct - 23 Oct

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

A stone building with outdoor seating and a garden with roses.

Borgo San Felice Resort

Castelnuovo Berardenga

NZ$1,470

includes taxes & fees

11 Oct - 12 Oct

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

A restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.

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

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

Hotel Le Fontanelle

Castelnuovo Berardenga

NZ$992

includes taxes & fees

21 Oct - 22 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.

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

A large indoor swimming pool with clear water, surrounded by modern architecture and a glass railing.

The Club House

Castelnuovo Berardenga

NZ$1,356

includes taxes & fees

21 Oct - 22 Oct

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.

An outdoor dining area with tables and chairs, a chef preparing food, and a scenic view in the background.

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

COMO Castello Del Nero

Tavarnelle Val di Pesa

NZ$1,654

includes taxes & fees

17 Oct - 18 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

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village

10/10 Excellent

"Perfect can’t fault it. Maybe a bigger train/bus at peak times would help. Lovely restaurant, bars, ice cream. Clean swimming pools. Good, kind, friendly staff. Safe place. Clean accommodation. Peaceful environment. Must take mosquito treatment as they’re bad out here. Lovely bonus is the pump at the pools to pump donuts up. Can’t fault it. Will 100000% return."

Relais Vignale & Spa

Relais Vignale & Spa

10/10 Excellent

"Beautiful small medieval town with castle and narrow streets. Close to wineries but not much else to do….location is very beautiful on top of hill."

Park Hotel Chianti

Park Hotel Chianti

10/10 Excellent

"The staff are very helpful and kind."

Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent

"very nice historic hotel with great views of the country side and great atmphere. Room size and ammenities were wonderful. The breakfeast was great. Restaurant was nice with historic dishes. Only down side was the gluten and nut free options were limited...mainly for gluten sufferers, since the only gluten free pasta is Penne, which is not great for all dishes and frustratingsince Italy produces a very large variety of great gluten free pasta shapes. Also, my travel partner and I did the same pasta, one gluten free (penne) and one not gluten free. The non-gluten-free pasta came beautifully presented, while the gluten-free pasta came like it was thrown together last minute… like as if you were sitting at your own kitchen table. Impression given with the dinner is that people with allergies, are more a bit of a bother, and the typical mission in Italy, to give visitors an excellent culinary experience, is more less abandoned for people with allergies. that said, accommodating allergies is very difficult these days and at least the menu was clear about which foods contain which allergens."

Palagina la Dimora

Palagina la Dimora

8/10 Good

"Nice property to relax. Pool is nice. Breakfast is meh but works. Room was spacious although felt outdated and lacking lighting. Some staff were very helpful while some could have been more friendly."

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"The experience was exceptional, the dinners in both restaurants on site were spectacular. The staff was amazing, friendly, and made our stay very memorable. We are planning to return soon."

COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent

"The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back."

Borgo Vescine

Borgo Vescine

10/10 Excellent

"⭐️⭐️⭐️⭐️⭐️ We genuinely did not want to leave Borgo Vescine was everything we hoped a stay in Tuscany would be. The property is absolutely stunning, incredibly peaceful, and so beautifully cared for that once we arrived, we honestly didn’t want to leave. What made the experience even more special was the staff. Everyone we encountered was warm, welcoming and genuinely delightful. The hospitality never felt forced or overly formal. We simply felt very well taken care of throughout our stay. We had dinner at the property and the restaurant was excellent, which made staying in for the evening an easy decision. Breakfast was included with our stay and was such a delicious treat each morning. Being able to wake up somewhere this beautiful, have a wonderful breakfast and then simply enjoy the property was exactly the kind of Tuscan experience we were looking for. The grounds themselves are gorgeous and meticulously maintained, with beautiful views and so many quiet little areas to sit and take everything in. Despite everything the property offers, it still feels serene, intimate and wonderfully quiet. Borgo Vescine is the kind of place that makes you reconsider whatever plans you had for the day because you would rather just stay there. One of our favorite stays in Tuscany and a property I would happily return to. Highly recommend."

Villa Le Barone

Villa Le Barone

10/10 Excellent

"Excellent stay with wonderful , friendly staff!"

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