A stone building with a clock tower, steps leading up to it, and people walking around.

Castellina in Chianti Hotel Guide - Hotels with Pool in Castellina in Chianti, Tuscany

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Check availability on Castellina in Chianti Hotels with Pool

Tonight
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Castellina in Chianti hotels with a pool

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 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.

1. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
  • Countryside farm stay's outdoor pool beckons with scenic vineyard views.
€91
includes taxes & fees
25 Oct - 26 Oct
Borgo di Pietrafitta Relais
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 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.

2. 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.
€201
includes taxes & fees
2 Nov - 3 Nov
Castello La Leccia
A clear blue pool with lounge chairs and a stone building in the background.
A stone building with a wooden bench outside.
A rustic interior with a brick archway, wooden beams, a bar area, and potted plants.
A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.

3. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
  • Sun-drenched Tuscan pool retreat offers garden-framed relaxation and poolside cocktails.
€123
includes taxes & fees
18 Oct - 19 Oct
Hotel Colle Etrusco Salivolpi
A poolside area with lounge chairs and a view of the night sky.
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.
A person relaxing in a hot tub with a view of a building and trees in the background.

4. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
  • Scenic Tuscan escape with a poolside paradise and winery at your doorstep.
€111
includes taxes & fees
13 Oct - 14 Oct
Belvedere di San Leonino
A rectangular pool with clear water, surrounded by white lounge chairs and a grassy area.
A bathroom with a large sink, toilet, and walk-in shower.
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.

5. 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.
€196
includes taxes & fees
18 Oct - 19 Oct
Palazzo Squarcialupi
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
A bar area with brick arches, wooden barrels, leather seating, and a wine rack.
A view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.
A building with arched windows, a courtyard with a pond, and a metal fence.

6. Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
  • Sun-soaked seasonal pool oasis in the heart of a Tuscan wine resort with loungers and umbrellas.
€65
includes taxes & fees
12 Oct - 13 Oct
Hotel Casafrassi
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 sculpture of two figures in a garden with a windmill in the background.
A castle-like building with a swimming pool and a well-maintained garden.

7. 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.
€167
includes taxes & fees
26 Oct - 27 Oct
Agriturismo Villa Godenano - Pool & Suites
A pool area with lounge chairs and umbrellas, surrounded by greenery and trees.
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.
A stone staircase leading to a wooden balcony with a view of a mountainous landscape.

8. 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.
€153
includes taxes & fees
12 Oct - 13 Oct
Albergo Il Colombaio
A swimming pool with lounge chairs and an umbrella, surrounded by trees.
A spacious living room with two sofas, a coffee table, and a mural of trees on the walls.
A restaurant with stone walls, wooden furniture, and a wine cellar.
A room with a wooden floor, a bathtub, a chair, a bed, and large windows offering a view of the countryside.

9. Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
€259
includes taxes & fees
22 Oct - 23 Oct
Fattoria di Vegi
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, set against a stone building with a garden.
A stone building with multiple windows and a chimney.
A rustic interior with exposed wooden beams, a wooden dining table with wine bottles, a sofa, and a staircase leading to an upper level.
A stone building with a gravel driveway leading to a table set for dining, surrounded by greenery and a vineyard in the background.

10. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
€130
includes taxes & fees
8 Nov - 9 Nov
Agriturismo La Ferrozzola
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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 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 pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.
A courtyard with stone buildings, outdoor tables set for dining, and a gravel ground.

Castello La Leccia

Castello La Leccia
Castellina in Chianti
€201
includes taxes & fees
2 Nov - 3 Nov
Castello La Leccia
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 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
€91
includes taxes & fees
25 Oct - 26 Oct
Borgo di Pietrafitta Relais
A spa area with a stone ceiling, a large bathtub, and a seating area.
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.
A historic building with a courtyard, stone arches, and a tiled roof.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
€196
includes taxes & fees
18 Oct - 19 Oct
Palazzo Squarcialupi
A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.
A clear blue pool with lounge chairs and a stone building in the background.
A rustic interior with a brick archway, wooden beams, a bar area, and potted plants.
A stone building with a wooden bench outside.

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
€123
includes taxes & fees
18 Oct - 19 Oct
Hotel Colle Etrusco Salivolpi
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

Belvedere di San Leonino
Castellina in Chianti
€111
includes taxes & fees
13 Oct - 14 Oct
Belvedere di San Leonino
A stately building with a grand entrance, multiple arches, and a well-lit facade.
A spacious living room with two sofas, a coffee table, and a mural of trees on the walls.
A restaurant with stone walls, wooden furniture, and a wine cellar.
A well-decorated living room with a sofa, a coffee table, and a vase with flowers.

Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
€259
includes taxes & fees
22 Oct - 23 Oct
Fattoria di Vegi
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 sculpture of two figures in a garden with a windmill in the background.
A castle-like building with a swimming pool and a well-maintained garden.

Agriturismo Villa Godenano - Pool & Suites

Agriturismo Villa Godenano - Pool & Suites
Castellina in Chianti
€167
includes taxes & fees
26 Oct - 27 Oct
Agriturismo Villa Godenano - Pool & Suites
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 clear blue pool with lounge chairs and umbrellas, surrounded by lush greenery and a forested hillside.
A spacious living room with striped sofas, a coffee table, and a chandelier.

Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti
€156
includes taxes & fees
12 Oct - 13 Oct
Villa Casalecchi Country Hotel
A stone building with an arched entrance, a wooden door, and a small balcony with a railing.
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.
A stone-walled room with tables set for dining, a staircase, and a lamp.

Albergo Il Colombaio

Albergo Il Colombaio
Castellina in Chianti
€153
includes taxes & fees
12 Oct - 13 Oct
Albergo Il Colombaio
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.
A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.
A modern interior with a bar area, seating, and a staircase.
A vineyard landscape with rows of grapevines and a person holding a glass.

Locanda le Piazze

Locanda le Piazze
Castellina in Chianti
€366
includes taxes & fees
18 Oct - 19 Oct
Locanda le Piazze
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4-star hotels with pools in Castellina in Chianti

A spa area with a stone ceiling, a large bathtub, and a seating area.
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.
A historic building with a courtyard, stone arches, and a tiled roof.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
€196
includes taxes & fees
18 Oct - 19 Oct
Palazzo Squarcialupi
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

Belvedere di San Leonino
Castellina in Chianti
€111
includes taxes & fees
13 Oct - 14 Oct
Belvedere di San Leonino
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.
A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.
A modern interior with a bar area, seating, and a staircase.
A vineyard landscape with rows of grapevines and a person holding a glass.

Locanda le Piazze

Locanda le Piazze
Castellina in Chianti
€366
includes taxes & fees
18 Oct - 19 Oct
Locanda le Piazze
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 clear blue pool with lounge chairs and umbrellas, surrounded by lush greenery and a forested hillside.
A spacious living room with striped sofas, a coffee table, and a chandelier.

Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti
€156
includes taxes & fees
12 Oct - 13 Oct
Villa Casalecchi Country Hotel
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
A bar area with brick arches, wooden barrels, leather seating, and a wine rack.
A view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.
A building with arched windows, a courtyard with a pond, and a metal fence.

Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
€65
includes taxes & fees
12 Oct - 13 Oct
Hotel Casafrassi
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 Castellina in Chianti Hotel Reviews

Villa Neroli

Villa Neroli

10/10 Excellent
"Excelente alojamiento, nuestra habitación muy preciosa con una terraza gigante, el hotel es muy amplio vale la pena!!!"
Pablo 1-night trip
Posted 4 hours ago
Villa Neroli
Hu Firenze Camping In Town

Hu Firenze Camping In Town

10/10 Excellent
"Loved the place. Our cabin was perfect & it’s right on a bus line into town."
Debra 2-night trip
Posted 2 days ago
Hu Firenze Camping In Town
Plus Florence - Hostel

Plus Florence - Hostel

10/10 Excellent
"Buena ubicacion, habitacion limpia. Desayuno bueno, delicioso y barato. El personal del hotel muy amable y siempre dispuesto a ayudar. Definotivamente lo recomiendo 100%.🌻"
Sally 2-night trip
Posted 3 days ago
Plus Florence - Hostel

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 such as City Hall Castellina In Chianti and Castellina Fortress, and then kick back and relax poolside at one of the accommodation options 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 should I expect to find 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 settings 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 accommodation that offers an outdoor pool if you plan to visit Castellina in Chianti in the warmest months of August, July or June, when the average temperature is 22°C. Accommodation with an indoor pool may be what you want if you visit during the coldest months of January, February or December, when the average temp is 6°C.