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Check availability on Castellina in Chianti Hotels with a Pool

Tonight
Oct 1 - Oct 2
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Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Castellina in Chianti hotels with a pool

A pool with clear water and a row of white lounge chairs facing a scenic hillside view.
An outdoor patio with round tables and chairs, surrounded by potted plants and flowers.
A cozy living room with two beige sofas, a glass coffee table, and a patterned rug.
A stone-walled hallway with a staircase, a glass table with a red cushion, and a wooden cabinet.

1. Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
  • Dive into the tranquil waters of a seasonal outdoor pool surrounded by the charm of this Beaux Arts hotel and attached winery.
₩277,675
₩314,657 total
includes taxes & fees
Oct 21 - Oct 22
Palazzo Squarcialupi
A clear blue pool with lounge chairs and a stone building in the background.
A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.
A stone building with a wooden bench outside.
A rustic living room with exposed wooden beams, a sofa, a coffee table, and a dining area with chairs.

2. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
  • Sun-drenched Tuscan pool retreat offers garden-framed relaxation and poolside cocktails.
₩137,996
₩156,406 total
includes taxes & fees
Oct 26 - Oct 27
Hotel Colle Etrusco Salivolpi
A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.
A cozy living room with a fireplace, comfortable seating, and a rustic ceiling.
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.
A vineyard landscape with rows of grapevines and a person holding a glass.

3. Locanda le Piazze

Locanda le Piazze
Castellina in Chianti
  • Savor countryside luxury at the outdoor pool, where vineyard views and poolside cocktails create an idyllic Tuscan escape.
₩466,471
₩522,329 total
includes taxes & fees
Oct 12 - Oct 13
Locanda le Piazze
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 stone building with a courtyard, a covered seating area, and a small bell tower.
A cozy living room with a stone fireplace, striped sofas, and a coffee table.

4. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
  • Countryside farm stay's outdoor pool beckons with scenic vineyard views.
₩112,969
₩130,407 total
includes taxes & fees
Oct 25 - Oct 26
Borgo di Pietrafitta Relais
A pool with lounge chairs and umbrellas, surrounded by stone tiles and trees.
A long table set for dining in a tunnel with wine barrels on one side.
A spacious bedroom with a large bed, a desk, and a chair. There is a painting on the wall and a window with curtains.
A sculpture of two figures in a garden with a windmill in the background.

5. Agriturismo Villa Godenano - Pool & Suites

Agriturismo Villa Godenano - Pool & Suites
Castellina in Chianti
  • Dive into this Tuscan paradise with a seasonal pool and umbrellas for ultimate summer relaxation.
₩203,120
₩229,573 total
includes taxes & fees
Oct 28 - Oct 29
Agriturismo Villa Godenano - Pool & Suites
A swimming pool with lounge chairs and an umbrella, surrounded by trees.
A room with a wooden floor, a bathtub, a chair, a bed, and large windows offering a view of the countryside.
A spacious living room with two sofas, a coffee table, and a mural of trees on the walls.
A stately building with a grand entrance, multiple arches, and a well-lit facade.

6. Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
₩335,361
₩378,119 total
includes taxes & fees
Oct 25 - Oct 26
Fattoria di Vegi
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.
A courtyard with stone buildings, tables with white tablecloths, and chairs arranged for dining.

7. Castello La Leccia

Castello La Leccia
Castellina in Chianti
  • Castello La Leccia's seasonal pool offers Tuscan countryside refreshment and vineyard views all summer long.
₩370,110
₩413,262 total
includes taxes & fees
Oct 17 - Oct 18
Castello La Leccia
A clear blue pool with lounge chairs and umbrellas, surrounded by lush greenery and a forested hillside.
A bench in a park with a lamp post and a building in the background.
A spacious living room with striped sofas, a coffee table, and a chandelier.
A hallway with a wooden altar, benches, and a carpet with a floral pattern.

8. Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti
  • Tuscan poolside paradise boasts an outdoor swimming spot and a hot tub in scenic countryside settings.
₩187,910
₩215,912 total
includes taxes & fees
Oct 17 - Oct 18
Villa Casalecchi Country Hotel
A pool area with a view of vineyards and hills.
A stone building with a wooden door and a balcony with flower planters.
A buffet setup with various baked goods and pastries, including a bundt cake, arranged on a wooden table with a stone wall background.
An outdoor dining area with tables and chairs, a pergola structure, and potted plants.

9. Riserva di Fizzano Residence

Riserva di Fizzano Residence
Castellina in Chianti
  • Vineyard retreat's outdoor pool offers tranquil relaxation with Tuscan sunshine and idyllic views.
₩258,242
₩287,142 total
includes taxes & fees
Oct 4 - Oct 5
Riserva di Fizzano Residence
A pool area with lounge chairs and umbrellas, surrounded by greenery and trees.
A stone building with an arched entrance, a wooden door, and a small balcony with a railing.
A stone-walled room with tables set for dining, a staircase, and a lamp.
A stone building with a large arched doorway, a bench, and a potted plant outside.

10. Albergo Il Colombaio

Albergo Il Colombaio
Castellina in Chianti
  • Lounge beneath Italian sunshine at the inviting outdoor pool, where rural charm meets relaxation at this countryside retreat.
₩209,331
₩234,875 total
includes taxes & fees
Oct 5 - Oct 6
Albergo Il Colombaio
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Choose what matters most at hotels with a pool in Castellina in Chianti

Breakfast included
4 stars
5 stars
Spa
Hot tub

Hotels with pools and free breakfast in Castellina in Chianti

A long table set for dining in a tunnel with wine barrels on one side.
A pool with lounge chairs and umbrellas, surrounded by stone tiles and trees.
A spacious bedroom with a large bed, a desk, and a chair. There is a painting on the wall and a window with curtains.
A sculpture of two figures in a garden with a windmill in the background.

Agriturismo Villa Godenano - Pool & Suites

Agriturismo Villa Godenano - Pool & Suites
Castellina in Chianti
₩203,120
₩229,573 total
includes taxes & fees
Oct 28 - Oct 29
Agriturismo Villa Godenano - Pool & Suites
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 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.
A spa room with a stone ceiling, a circular hot tub, a window, and a bench.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
₩277,675
₩314,657 total
includes taxes & fees
Oct 21 - Oct 22
Palazzo Squarcialupi
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 stone building with a courtyard, a covered seating area, and a small bell tower.
A cozy living room with a stone fireplace, striped sofas, and a coffee table.

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
₩112,969
₩130,407 total
includes taxes & fees
Oct 25 - Oct 26
Borgo di Pietrafitta Relais
A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.
A stone building with a wooden bench outside.
A clear blue pool with lounge chairs and a stone building in the background.
A rustic living room with exposed wooden beams, a sofa, a coffee table, and a dining area with chairs.

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
₩137,996
₩156,406 total
includes taxes & fees
Oct 26 - Oct 27
Hotel Colle Etrusco Salivolpi
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.
A stone building with a wooden door and a balcony with flower planters.
A buffet setup with various baked goods and pastries, including a bundt cake, arranged on a wooden table with a stone wall background.
An outdoor dining area with tables and chairs, a pergola structure, and potted plants.

Riserva di Fizzano Residence

Riserva di Fizzano Residence
Castellina in Chianti
₩258,242
₩287,142 total
includes taxes & fees
Oct 4 - Oct 5
Riserva di Fizzano Residence
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
A building with arched windows, a courtyard with a pond, and a metal fence.
A view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.
A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
₩82,339
₩99,784 total
includes taxes & fees
Oct 6 - Oct 7
Hotel Casafrassi
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.
A spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.
A vineyard landscape with rows of grapevines and a person holding a glass.
A modern interior with a bar area, seating, and a staircase.

Locanda le Piazze

Locanda le Piazze
Castellina in Chianti
₩466,471
₩522,329 total
includes taxes & fees
Oct 12 - Oct 13
Locanda le Piazze
A stone building with an arched entrance, a wooden door, and a small balcony with a railing.
A stone staircase leading to a wooden balcony with a view of a mountainous landscape.
A stone building with a large arched doorway, a bench, and a potted plant outside.
A pool area with lounge chairs and umbrellas, surrounded by greenery and trees.

Albergo Il Colombaio

Albergo Il Colombaio
Castellina in Chianti
₩209,331
₩234,875 total
includes taxes & fees
Oct 5 - Oct 6
Albergo Il Colombaio
A stately building with a grand entrance, multiple arches, and a well-lit facade.
A well-decorated living room with a sofa, a coffee table, and a vase with flowers.
A spacious living room with two sofas, a coffee table, and a mural of trees on the walls.
A swimming pool with lounge chairs and an umbrella, surrounded by trees.

Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
₩335,361
₩378,119 total
includes taxes & fees
Oct 25 - Oct 26
Fattoria di Vegi
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 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 stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
₩176,589
₩203,459 total
includes taxes & fees
Oct 27 - Oct 28
Belvedere di San Leonino
View all properties

4-star hotels with pools in Castellina in Chianti

A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.
A spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.
A vineyard landscape with rows of grapevines and a person holding a glass.
A modern interior with a bar area, seating, and a staircase.

Locanda le Piazze

Locanda le Piazze
Castellina in Chianti
₩466,471
₩522,329 total
includes taxes & fees
Oct 12 - Oct 13
Locanda le Piazze
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 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.
A spa room with a stone ceiling, a circular hot tub, a window, and a bench.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
₩277,675
₩314,657 total
includes taxes & fees
Oct 21 - Oct 22
Palazzo Squarcialupi
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
A building with arched windows, a courtyard with a pond, and a metal fence.
A view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.
A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
₩82,339
₩99,784 total
includes taxes & fees
Oct 6 - Oct 7
Hotel Casafrassi
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 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 stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
₩176,589
₩203,459 total
includes taxes & fees
Oct 27 - Oct 28
Belvedere di San Leonino
A historic building with a stone facade, multiple windows with shutters, and a well-maintained garden with potted plants and flowers.
A bench in a park with a lamp post and a building in the background.
A spacious living room with striped sofas, a coffee table, and a chandelier.
A hallway with a wooden altar, benches, and a carpet with a floral pattern.

Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti
₩187,910
₩215,912 total
includes taxes & fees
Oct 17 - Oct 18
Villa Casalecchi Country Hotel
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.
View all properties

Top Castellina in Chianti Hotel Reviews

Italiana Hotels Florence

Italiana Hotels Florence

8/10 Good
"Greta place and friendly staff. Pool closed early in the month due to rain that was disappointing"
Jodie 2-night trip
Posted 1 day ago
Italiana Hotels Florence
Villa Neroli

Villa Neroli

10/10 Excellent
"The staff was amazing and very helpful on recommendations for dining/attractions. I will be back for breakfast - excellent selections and the staff was excellent!!"
Jennifer 3-night trip
Posted 4 days ago
Villa Neroli

Frequently asked questions

What's it like visiting Castellina in Chianti?
If spending time by the pool is your idea of the perfect getaway, you might want to think about relaxing Castellina in Chianti, which has 7 places to stay with pools. While you're here, you can explore attractions like City Hall Castellina In Chianti and Castellina Fortress, and then unwind poolside at one of the accommodations in Castellina in Chianti that guests like for their pools.
What are some hotels with pools in Castellina in Chianti?
Residenzia del Sogno: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Podere Palazzolo: Offers a sauna, a seasonal outdoor pool, and spa services.
How many hotels with pools are there in Castellina in Chianti?
Expedia has 7 hotels in Castellina in Chianti for your poolside break.
What is there to see and do in Castellina in Chianti?
The picturesque setting of Chianti Sculpture Park and Sentierelsa Trail showcase the area's natural beauty. Discover sights such as City Hall Castellina In Chianti, Castellina Fortress, and Archaeological Museum of Chianti during your stay. The countryside and wineries are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Castellina in Chianti?
You may want to consider an accommodation with an outdoor swimming pool if you will be visiting Castellina in Chianti in the warmest months of August, July, or June when the average temperature is 72°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 44°F.

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